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1 Electronic upplementary Material (EI) for RC dvances. This journal is The Royal ociety of Chemistry 204 upporting Information for ynthesis of thiazolidines via regioselective addition of unsymmetric thioureas to maleic acid derivatives lena. Pankova,* Mikhail. amartsev, Igor. hulgin, Pavel R. Golubev, Margarita. vdontceva, Mikhail. Kuznetsov Experimental section Copies of the and 3 C MR spectra Copies of the 5 - MC spectra References. 77

2 Experimental ection General Information: MR spectroscopic data were recorded with ruker DPX-300, ruker vance 400 and ruker vance 500 spectrometers (300.3, and Mz for, 75.47, 00.6 and Mz for 3 C, respectively) in CDCl 3 and DM-d 6 and were referenced to residual solvent proton signals (δ = 7.26 and 2.50 ppm, respectively) and solvent carbon signals (δ C = and ppm, respectively). DEPT spectra were used for carbon atoms signals assignment. The MR spectroscopic signals of the thiazolidines atoms on the phenyl ring of former thiourea are referred to as and the atoms on the phenyl ring of former maleimide to as. The diastereotopic protons of the C 2 -group of thiazolidines are marked by a and b. Melting points were determined with a tuart MP30 instrument and are uncorrected. Mass spectra were recorded with a ruker Maxis RM-EI-qTF spectrometer (electrospray ionization mode). ingle crystal X-ray data were obtained using an gilent Technologies uperova tlas and an gilent Technologies Xcalibur Eos diffractometers. The samples were measured at a temperature of 00 K. The structures have been solved by the direct methods and refined by means of the ELXL 97 program incorporated in the LEX2 program package. 2 The carbon-bound atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U iso () set to.2u eq (C) and C 0.97 Å for the C 2 groups and U iso () set to.5u eq () and C 0.96 Å for the C 3 groups. Empirical absorption correction was applied in Cryslis Pro program complex 3 using spherical harmonics, implemented in CLE3 PCK scaling algorithm. Column chromatography was performed with Merck silica gel 60 ( mesh). For TLC analysis lugram IL G/UV 254 (Macherey-agel) plates were used. -enzyl- -phenylthiourea 4 was already available in our laboratory. General procedure for the preparation of thioureas 3a-j. 5 tirred mixture of appropriate amine (23 mmol) and isothiocyanate (23 mmol) in ethanol (25 ml) was refluxed until the reaction completion indicated by TLC. The reaction mixture was cooled in an ice bath, a precipitate was filtered and recrystallized from ethanol. -Ethyl- -(4-methoxyphenyl)thiourea (3a). Pale beige crystals, yield 3.6 g (75%), mp C (lit C). Н MR (400 Мz, CDCl 3 ): δ =.5 (t, J = 7.2 z, 3, C 2 C 3 ); 3.65 (dq, J = 5.5, 7.2 z, 2, C 2 ); 3.82 (s, 3, C 3 ); 5.74 (br s,, ); (m, 2, m ); (m, 2, o ); 7.55 (br s,, ) ppm. -Ethyl- -(4-methylphenyl)thiourea (3b). 7 Colorless crystals, yield 3.26 g (73%), mp C (lit C). Н MR (400 Мz, CDCl 3 ): δ =.6 (t, J = 7.2 z, 3, C 2 C 3 ); 2.36 (s, 3, C 3 ); 3.65 (dq, J = 5.4, 7.3 z, 2, C 2 ); 5.89 (br s,, ); 7.08 (d, J = 8.2 z, 2, m ); 7.22 (d, J = 8.2 z, 2, o ); 7.72 (br s,, ) ppm. 2

3 -Ethyl- -phenylthiourea (3c). 9 Colorless crystals, yield 2.57 g (62%), mp 00-0 С (lit С). Н MR (400 Мz, CDCl 3 ): δ =.8 (t, J = 7.2 z, 3 Н, С 3 ); 3.67 (dq, J = 6.8, 7.2 z, 2 Н, C 2 ); 5.97 (br s, Н, ); 7.20 (d, J = 7.5 z, 2 Н, o ); 7.30 (t, J = 7.5 z, Н, p ); (m, 2 Н, m ); 7.79 (br s, Н, ) ppm. -(4-Chlorophenyl)- -ethylthiourea (3d). 7 Colorless crystals, yield 3.80 g (77%), mp 6-7 С (lit. 9 С). Н MR (400 Мz, CDCl 3 ): δ =.9 (t, J = 7.3 z, 3, C 3 ); 3.65 (dq, J = 7.3, 7.3 z, 2, C 2 ); 5.90 (br s,, ); 7.6 (d, J = 8.5 z, 2, o ); 7.39 (d, J = 8.5 z, 2, m ); 7.95 (br s,, ) ppm. -Ethyl- -(4-fluorophenyl)thiourea (3e). Pale beige crystals, yield 3.8 g (70%), mp С (lit С). Н MR (400 Мz, CDCl 3 ): δ =.6 (t, J = 7.2 z, 3, C 3 ); 3.65 (dq, J = 7.0, 7.3 z, 2, C 2 ); 5.84 (br s,, ); (m, 2, o ); (m, 2, m ); 8.3 (br s,, ) ppm. 3 C MR (00 Мz, CDCl 3 ): δ = 4.2 (C 3 ); 40.2 (C 2 ); 7.0 (d, J = 22.7 z, C m ); 27.8 (d, J = 8.7 z, C o ); 32.0 (d, J = 2.6 z, C i ); 6.4 (d, J = z, C p ); 80.7 (C=) ppm. -Ethyl- -(4-nitrophenyl)thiourea (3f). Yellow crystals, yield 3.39 g (66%), mp С (lit С). Н MR (400 Мz, DM-d 6 ): δ =.5 (t, J = 7.2 z, 3 Н, С 3 ); (m, 2 Н, C 2 ); (m, 2 Н, o ); (m, 2 Н, m ); 8.26 (br s, Н, ); 0.06 (br s, Н, ) ppm. 3 C MR (00 Мz, DM-d 6 ): δ = 3.7 (C 3 ); 38.8 (C 2 ); 20.3, 24.5 (C m,o ); 4.7, 46.4 (C i,p ); 79.8 (C=) ppm. -(2,6-Dimethylphenyl)- -methylthiourea (3g). 3 Pink crystals, yield 3.3 g (70%), mp С (lit С). Н MR (400 Мz, CDCl 3 ): δ = 2.26 (s, 6, 2 C 3 ); 3.09 (d, J = 4.7 z, 3, C 3 ); 5.36 (br s,, ); 7.4 (d, J = 7.4 z, 2, m ); (m,, p ); 7.35 (br s,, ) ppm. -Isopropyl- -phenylthiourea (3h). 5 Colorless crystals, yield 3.44 g (77%), mp 0-02 С (lit. 6 0 С) Н MR (400 Мz, CDCl 3 ): δ =.20 (d, J = 6.6 z, 6 Н, C(С 3 ) 2 ); 4.60 (dsept, J = 6.6, 6.6 z, Н, C(С 3 ) 2 ); 5.79 (br s, Н, ); 7.8 (d, J = 7.6 z, 2 Н, o ); (m, Н, p ); (m, 2 Н, m ); 7.67 (br s, Н, ) ppm. -Cyclohexyl- -phenylthiourea (3i). 7 Colorless crystals, yield 4.67 g (87%), mp 5-53 С (lit С) Н MR (400 Мz, CDCl 3 ): δ = (m, 3 Н, с-нех); (m, 2 Н, с-нех); (m, 3 Н, с-нех); (m, 2 Н, с-нех); (br s, Н, С); 5.89 (br s, Н, ); 7.8 (d, J = 7.6 z, 2 Н, o ); (m, Н, p ); (m, 2 Н, m ); 7.75 (br s, Н, ) ppm. -tert-utyl- -phenylthiourea (3j). 9 Colorless crystals, yield 3.96 g (83%), mp С (lit С). Н MR (400 Мz, DM-d 6 ): δ =.47 (s, 9, 3 C 3 ); (m,, 3

4 p ); (m, 2, o ); 7.35 (br s,, ); 7.43 (d, J = 7.6 z, 2 Н, m ); 9.26 (br s,, ) ppm. -Ethyl- -isopropylthiourea (3k). Isopropylamine (.0 ml, 0.69 g,.7 mmol) was added to a stirred solution of ethylisothiocyanate (.0 ml,.02 g,.7 mmol) in diethyl ether (5 ml). fter 2 h a precipitate was filtered, washed with diethyl ether (0 ml) and dried. Colorless crystals, yield.42 g, 83%, mp С. Н MR (400 Мz, DM-d 6 ): δ =.04 (t, J = 7.2 z, 3, C 2 C 3 );.08 (d, J = 6.5 z, 6 Н, C(С 3 ) 2 ); 3.34 (br s, 2, C 2 ); 4.22 (br s,, C); 7. (br s,, ); 7.6 (br s,, ) ppm. Н MR (400 Мz, CDCl 3 ): δ =.22 (t, J = 7.2 z, 3, C 2 C 3 );.23 (d, J = 6.5 z, 6 Н, C(С 3 ) 2 ); 3.42 (br s, 2, C 2 ); 4.23 (br s,, C); 5.57 (br s,, ); 5.73 (br s,, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 4. (C 2 C 3 ); 22.5 (C(С 3 ) 2 ); 38.9 (C 2 ); 46.0 (C); 80. (C=) ppm. RM (EI), m/z: calcd for C [M+] , found General procedure for the preparation of thiazolidines 5aa-ff, 5ga-gf. tirred mixture of thiourea 3a-g ( mmol) and -arylmaleimide 4a-g ( mmol) in i-pr (5 ml) was refluxed for 3-5 h, and then was poured into water (30 ml). precipitate was filtered, washed with water and recrystallized from ethanol/water (:) mixture. 2-(3-Ethyl-2-(4-methoxyphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methoxyphenyl)- acetamide (5aa). eige crystals, yield 320 mg (77%), mp 7-72 C. Me Н MR (300 Мz, CDCl 3 ): δ =.29 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.76 (dd, J = 6., 0.0 z, Н, Н а ); 3.32 (dd, J = 6., 3.99 (m, 2 Н, С 2 СН 3 ); 4.42 (dd, J = 0.0, 3.8 z, Н, C); (m, 6, m, o,m ); 7.34 (d, J = 8.9 z, 2 Н, o ); 7.65 (br s, Н, ) ppm. 3 С MR (75 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.2, 40.3 (СН 2 ); 43.8 (C); 55.4 (2 C 3 ); 4., 4.5 (С m, С m ); 2.8, 22. (С o, С o ); 30.4 (C i ); 4. (C i ); 53.2 (С=); 56.6, 56.7 (С p, С p ); 66.9, 73.9 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found z, Н, b ); 3.76 (s, 3 Н, ОC 3 ); 3.78 (s, 3 Н, ОC 3 ); (3-Ethyl-2-(4-methoxyphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methylphenyl)- acetamide (5ab). eige crystals, yield 30 mg (76%), mp C. Me Me Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.29 (s, 3, C 3 ); 2.79 (dd, J = 6.2, 9.9 z, Н, Н а ); 3.35 (dd, J = 6.2, 4.0 z, Н, b ); 3.79 (s, 3 Н, ОC 3 ); (m, 2 Н, С 2 СН 3 ); 4.44 (dd, J = 9.9, 4.0 z, Н, C);

5 (m, 2, m ); (m, 2, o ); 7.0 (d, J = 8.2 z, 2 Н, m ); 7.34 (d, J = 8.2 z, 2 Н, o ); 7.46 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 20.8 (C 3 ); 38.2, 40.4 (СН 2 ); 43.8 (C); 55.4 (C 3 ); 4.4 (С m ); 9.9 (С o ); 22. (С o ); 29.5 (С m ); 34.3, 34.7 (C i,p ); 4. (C i ); 53.3 (С=); 56.7 (С p ); 67.0, 73.9 (С=О) ppm. Me RM (EI), m/z: calcd for [M+] , found (3-Ethyl-2-(4-methoxyphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide Pale yellow crystals, yield 295 mg (80%), mp C. (5ac). Н MR (300 Мz, CDCl 3 ): δ =.30 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.80 (dd, J = 6.3, 0.0 z, Н, Н а ); 3.37 (dd, J = 6.3, 3.6 z, Н, b ); 3.78 (s, 3 Н, ОC 3 ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 0.0, 3.6 z, Н, C); (m, 4, m,o ); (m, Н, Н p ); (m, 2 Н, Н m ); 7.46 (d, J = 8. z, 2 Н, o ); 7.80 (br s, Н, ) ppm. 3 С MR (75 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.3, 40.5 (СН 2 ); 43.7 (C); 55.4 (C 3 ); 4.5 (С m ); 9.9 (С o ); 22. (С o ); 24.6 (С p ); 29.0 (С m ); 37.3 (C i ); 4. (C i ); 53.2 (С=); 56.8 (С p ); 67., 73.9 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found acetamide (5ad). Colorless crystals, yield 284 mg (68%), mp C. Me Н MR (400 Мz, DM-d 6 ): δ =.20 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.93 (dd, J = 6.6, 9.4 z, Н, Н а ); 3.24 (dd, J = 6.6, 3.5 z, Н, b ); 3.73 (s, 3 Н, C 3 ); (m, 2 Н, С 2 СН 3 ); 4.54 (dd, J = 9.4, 3.5 z, Н, C); (m, 4 Н, Н o,m ); 7.34 (d, J = 8.8 z, 2 Н, Н m ); 7.55 (d, J = 8.8 z, 2 Н, Н o ); 0.25 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.4, 38.7 (СН 2 ); 43.3 (C); 55.2 (C 3 ); 4.4 (С m ); 20.6, 22.0 (С o, ); 26.9 (C p ); 28.7 (С m ); 37.6 (C i ); 4.2 (C i ); 54., 56. (С=, С p ); 67.9, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C Cl 3 3 [M+] , found (4-Chlorophenyl)-2-(3-ethyl-2-(4-methoxyphenyl)imino-4-oxo-,3-thiazolidin-5-yl)- 2-(3-Ethyl-2-(4-methoxyphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-fluorophenyl)- acetamide (5ae). Colorless crystals, yield 320 mg (80%), mp C. Me Cl F Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.80 (dd, J = 6.2, 9.9 z, Н, Н а ); 3.34 (dd, J = 6.2, 4.0 z, Н, b ); 3.79 (s, 3 Н, C 3 ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 9.9, 4.0 z, Н, C); (m, 4, m,o ); (m, 2 Н, Н m ); (m, 2 Н, Н o ); 7.64 (br s, Н, ) ppm. 5

6 3 С MR (75 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.3, 40.4 (СН 2 ); 43.7 (C); 55.4 (C 3 ); 4.5 (С m ); 5.7 (d, J = 22.2 z, С m ); 2.7 (d, J = 8. z, С o ); 22. (С o ); 33.3 (d, J = 2.4 z, C i ); 4.0 (C i ); 53.0, 56.8 (С=, C p ); 59.5 (d, J = z, С p ); 67., 73.9 (С=О) ppm. RM (EI), m/z: calcd for C F 3 3 [M+] , found acetamide (5af). Yellow crystals, yield 334 mg (78%), mp C. Me Н MR (300 Мz, CDCl 3 ): δ =.3 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.89 (dd, J = 6.5, 9. z, Н, Н а ); 3.42 (dd, J = 6.5, 4.4 z, Н, b ); 3.79 (s, 3 Н, ОC 3 ); (m, 2 Н, С 2 СН 3 ); 4.46 (dd, J = 9., 4.4 z, Н, C); (m, 4, m,o ); 7.69 (d, J = 9.0 z, 2 Н, Н o ); 8.9 (d, J = 9.0 z, 2 Н, m ); 8.48 (br s, Н, ) ppm. 3 С MR (75 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.5, 40.8 (СН 2 ); 43.3 (C); 55.4 (C 3 ); 4.5 (С m ); 9.9, 22.0, 25. (C o, С o,m ); 40.9, 43.3, 43.7 (C i, C i,p ); 52.5 (С=); 56.9 (С p ); 67.6, 74. (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found acetamide (5ba). Colorless crystals, yield 275 mg (69%), mp C. Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.2 z, 3 Н, C 2 C 3 ); 2.3 (s, 3 Н, C 3 ); 2.76 (dd, J = 6.2, 9.9 z, Н, Н а ); 3.32 (dd, J = 6.2, 3.9 z, Н, b ); 3.76 (s, 3 Н, ОC 3 ); (m, 2 Н, С 2 СН 3 ); 4.42 (dd, J = 9.9, 3.9 z, Н, C); (m, 4 Н, Н m, o ); 7.2 (d, J = 8. z, 2 Н, m ), (m, 2 Н, Н o ); 7.59 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 20.9 (C 3 ); 38.2, 40.3 (СН 2 ); 43.8 (C); 55.4 (C 3 ); 4. (С m ); 20.8, 22.0 (С o, С o ); 29.8 (С m ); 30.3, 34. (C p, C i ); 45.4 (C i ); 53.3 (С=); 56.6 (С p ); 66.9, 73.9 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (3-Ethyl-2-(4-methoxyphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-nitrophenyl)- 2-(3-Ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methoxyphenyl)- 2-(3-Ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methylphenyl)- acetamide (5bb). Colorless crystals, yield 304 mg (80%), mp C. Me 2 Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.30 (s, 3, C 3 ); 2.32 (s, 3, C 3 ); 2.78 (dd, J = 6.0, 9.9 z, Н, Н а ); 3.35 (dd, J = 6.0, 4.0 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.44 (dd, J = 9.9, 4.0 z, Н, C); 6.86 (d, J = 8. z, 2, o ); (m, 4, m, m ); 7.33 (d, J = 8.2 z, 2, o ); 7.44 (br s, Н, ) ppm. 6

7 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 20.8, 20.9 (C 3 ); 38.2, 40.5 (СН 2 ); 43.8 (C); 9.9, 20.8 (С o, С o ); 29.5, 29.8 (С m, С m ); 34., 34.3, 34.7 (C p, C i,p ); 45.4 (C i ); 53.3 (С=); 66.9, 73.9 (С=О) ppm. RM (EI), m/z: calcd for [M+] , found (3-Ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide Colorless crystals, yield 268 mg (73%), mp 9-92 C. (5bc). Н MR (300 Мz, CDCl 3 ): δ =.30 (t, J = 7. z, 3 Н, C 2 С 3 ); 2.32 (s, 3 Н, C 3 ); 2.79 (dd, J = 6.3, 0.0 z, Н, Н а ); 3.36 (dd, J = 6.3, 3.7 z, Н, b ); (m, 2 Н, C 2 С 3 ); 4.43 (dd, J = 0.0, 3.7 z, Н, C); 6.86 (d, J = 8.2 z, 2 Н, Н o ); (m, 3 Н, Н p, Н m ); (m, 2 Н, Н m ); 7.45 (d, J = 7.8 z, 2 Н, o ); 7.72 (br s, Н, ) ppm. 3 С MR (75 Мz, CDCl 3 ): δ = 2.6 (C 2 С 3 ); 20.9 (C 3 ); 38.3, 40.6 (СН 2 ); 43.8 (C); 9.9, 20.8 (С o, С o ); 24.6 (С p ); 29.0, 29.8 (С m, С m ); 34.2 (C p ); 37.3 (C i ); 45.4 (С i ); 53.2 (С=); 67., 73.9 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (4-Chlorophenyl)-2-(3-ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)- acetamide (5bd). Colorless crystals, yield 307 mg (76%), mp C. Н MR (400 Мz, DM-d 6 ): δ =.20 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.25 (s, 3 Н, C 3 ); 2.94 (dd, J = 6.6, 9.5 z, Н, Н а ); 3.26 (dd, J = 6.6, 3.7 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.54 (dd, J = 9.5, 3.7 z, Н, C); 6.8 (d, J = 8.2 z, 2 Н, Н o ); 7.3 (d, J = 8.2 z, 2 Н, Н m ); 7.34 (d, J = 8.8 z, 2 Н, Н m ); 7.55 (d, J = 8.8 z, 2 Н, Н o ); 0.25 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 20.4 (C 3 ); 37.4, 38.7 (СН 2 ); 43.3 (C); 20.6, 20.8 (С o, С o ); 28.7, 29.6 (С m, С m ); 26.9 (С p ); 33. (С p ); 37.6 (C i ); 45.7 (C i ); 54.2 (С=); 67.9, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C Cl 3 2 [M+] , found (3-Ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-fluorophenyl)acetamide (5be). Colorless crystals, yield 284 mg (74%), mp 60-6 C. Cl F Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.32 (s, 3 Н, C 3 ); 2.79 (dd, J = 6.2, 9.6 z, Н, Н а ); 3.34 (dd, J = 6.2, 4.0 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 9.6, 4.0 z, Н, C); 6.86 (d, J = 8.2 z, 2 Н, Н o ); (m, 2 Н, Н m ); 7.2 (d, J = 8.2 z, 2 Н, Н m ); (m, 2 Н, Н o ); 7.69 (br s, Н, ) ppm. 7

8 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 20.9 (C 3 ); 38.3, 40.4 (СН 2 ); 43.7 (C); 5.7 (d, J = 22.7 z, С m ); 20.8 (С o ); 2.7 (d, J = 7.8 z, С o ); 29.8 (С m ); 33.3 (d, J = 2.9 z, C i ); 34.3 (C p ); 45.3 (C i ); 53. (С=); 59.5 (d, J = z, С p ); 67., 74.0 (С=О) ppm. MKC989 RM (EI), m/z: calcd for C F 3 2 [M+] , found (3-Ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-nitrophenyl)acetamide (5bf). eige crystals, yield 326 mg (79%), mp C. Н MR (400 Мz, CDCl 3 ): δ =.3 (t, J = 7.2 z, 3 Н, C 2 C 3 ); 2.32 (s, 3 Н, C 3 ); 2.89 (dd, J = 6.5, 9.3 z, Н, Н а ); 3.43 (dd, J = 6.5, 4.4 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.45 (dd, J = 9.3, 4.4 z, Н, C); 6.86 (d, J = 8. z, 2 Н, Н o ); 7.3 (d, J = 8. z, 2 Н, Н m ); 7.69 (d, J = 8.8 z, 2 Н, o ); 8.8 (d, J = 8.8 z, 2 Н, m ); 8.52 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 20.9 (C 3 ); 38.5, 40.8 (СН 2 ); 43.3 (C); 9.2, 20.7 (С o, С o ); 25. (С m ); 29.9 (С m ); 34.4 (C p ); 43.3, 43.7 (C i,p ); 45. (C i ); 52.6 (С=); 67.6, 74. (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found Ethyl 4-(((3-ethyl-2-(4-methylphenyl)imino-4-oxo-,3-thiazolidin-5-yl)acetyl)amino)benzoate (5bg). eige crystals, yield 244 mg (56%), mp C. Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.2 z, 3 Н, C 2 C 3 );.38 (t, J = 7.2 z, 3 Н, ОC 2 C 3 ); 2.32 (s, 3 Н, C 3 ); 2.84 (dd, J = 6.5, 9.8 z, Н, Н а ); 3.40 (dd, J = 6.5, 4.0 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.35 (q, J = 7.2 z, 2 Н, C 2 C 3 ); 4.44 (dd, J = 9.8, 4.0 z, Н, C); 6.86 (d, J = 8. z, 2 Н, Н o ); 7.2 (d, J = 8. z, 2 Н, Н m ); 7.56 (d, J = 8.5 z, 2 Н, Н m ); 7.97 (d, J = 8.5 z, 2 Н, Н o ); 8.20 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 4.3 (СН 2 СН 3 ); 20.9 (C 3 ); 38.3, 40.7 (CC 2, СН 2 ); 43.6 (C); 60.9 (СН 2 ); 8.8, 20.8 (С o, С m ); 26.2 (C i ); 29.8, 30.8 (С m, С o ); 34.3 (C p ); 4.5 (C p ); 45.3 (C i ); 53.0 (С=); 67., 66.4, 74.0 (3 С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (3-Ethyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--(4-methoxyphenyl)acetamide 2 C 2 Et Me eige crystals, yield 27 mg (7%), mp 8-83 C. (5ca). Н MR (400 Мz, СDCl 3 ): δ =.3 (t, J = 7.2 z, 3 Н, C 2 C 3 ); 2.77 (dd, J = 6.2, 0.0 z, Н, Н а ); 3.43 (dd, J = 6.2, 3.8 z, Н, b ); 3.76 (s, 3 Н, C 3 ); (m, 2 Н, С 2 СН 3 );

9 (dd, J = 0.0, 3.8 z, Н, C); 6.82 (d, J = 8.8 z, 2 Н, Н m ); 6.96 (d, J = 7.6 z, 2 Н, Н o ); 7. (t, J = 7.3 z, Н, Н p ); (m, 4 Н, Н m, Н o ); 7.59 (br s, Н, ) ppm. 3 С MR (00 Мz, СDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.2, 40.2 (СН 2 ); 43.9 (C); 55.4 (C 3 ); 4. (С m ); 2.0, 2.8 (С o, С o ); 24.6 (C p ); 29.2 (С m ); 30.3 (C i ); 48.0 (C i ); 53.6 (С=); 56.6 (С p ); 66.9, 73.9 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (3-Ethyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--(4-methylphenyl)acetamide Colorless crystals, yield 287 mg (78%), mp 79-8 C. (5cb). Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.2 z, 3 Н, C 2 C 3 ); 2.30 (s, 3, C 3 ); 2.79 (dd, J = 6.2, 0. z, Н, Н а ); 3.35 (dd, J = 6.2, 3.8 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.44 (dd, J = 0., 3.8 z, Н, C); 6.96 (d, J = 7.3 z, 2, o ); (m, 3, p, m ); (m, 4, m, o ); 7.48 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 20.8 (C 3 ); 38.2, 40.3 (СН 2 ); 43.9 (C); 20.0, 2.0 (С o, С o ); 24.6 (C p ); 29.2, 29.5 (С m, С m ); 34.3, 34.7 (C i,p ); 47.9 (C i ); 53.7 (С=); 67.0, 73.9 (С=О) ppm. RM (EI), m/z: calcd for [M+] , found (3-Ethyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--phenylacetamide (5cc). Colorless crystals, yield 243 mg (69%), mp C. MR (400 Mz, DM-d 6 ): δ =.2 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.94 (dd, J = 6.8, 9.8 z, Н, Н а ); 3.25 (dd, J = 6.8, 3.5 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.56 (dd, J = 9.8, 3.5 z, Н, C); 6.93 (d, J = 7.6 z, 2 Н, Н o ); (m, Н, p ), (m, Н, p ); (m, 4 Н, Н m, Н m ); 7.52 (d, J = 7.6 z, 2 Н, Н o ); 0. (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.4, 38.7 (СН 2 ); 43.5 (C); 9., 2.0 (С o, С o ); 23.4, 24.2 (С p, С p ); 28.2, 29.2 (С m, С m ); 38.7 (C i ); 48.2 (C i ); 54.6 (С=); 67.7, 73.6 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (4-Chlorophenyl)-2-(2-phenylimino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)acetamide Cl Colorless crystals, yield 283 mg (73%), mp C. (5cd). Н MR (400 Мz, CDCl 3 ): δ =.3 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.82 (dd, J = 6.3, 0.0 z, Н, Н а ); 3.36 (dd, J = 6.3, 3.7 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.44 (dd, J = 0.0, 3.7 z, Н, C); 6.96 (d, J = 8.6 z, 2 Н, o ); (m, Н, Н p ); (m, 2 Н, m ); (m, 2 Н, m ); 7.42 (d, J = 8.8 z, 2 Н, o ); 7.65 (br s,, ) ppm. 9

10 3 С MR (00 Мz, CDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.3, 40.4 (СН 2 ); 43.7 (C); 20.9, 2.0 (С o, С o ); 24.7 (С p ); 29.0, 29.2 (С m, С m ); 29.7 (C p ); 35.9 (C i ); 47.9 (С i ); 53.3 (С=); 67.0, 73.9 (С=О) ppm. RM (EI), m/z: calcd for C 9 8 Cl 3 2 [M+] , found (3-Ethyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--(4-fluorophenyl)acetamide Colorless crystals, yield 285 mg (77%), mp 5-53 C. (5ce). Н MR (400 Мz, СDCl 3 ): δ =.3 (t, J = 7.2 z, 3 Н, C 2 C 3 ); 2.80 (dd, J = 6.3, 9.9 z, Н, Н а ); 3.35 (dd, J = 6.3, 3.8 z, Н, b ); 7.0 (m, 4 Н, Н o, Н m ); (m, Н, Н p ); (m, 2 Н, Н m ); (m, 2 Н, Н o ); 7.78 (br s, Н, ) ppm. 3 С MR (00 Мz, СDCl 3 ): δ = 2.6 (СН 2 СН 3 ); 38.3, 40.3 (СН 2 ); 43.7 (C); 5.7 (d, J = 22.6 z, С m ); 2.0 (С o ); 2.7 (d, J = 8. z, С o ); 24.7 (С p ); 29.2 (С m ); 33.2 (d, J = 2.2 z, С i ); 47.9 (C i ); 53.4 (С=); 59.5 (d, J = z, С p ); 67., 73.9 (С=О) ppm. RM (EI), m/z: calcd for C 9 8 F 3 2 [M+] , found (3-Ethyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--(4-nitrophenyl)acetamide Yellow crystals, yield 3 mg (78%), mp C. (5cf). Н MR (400 Мz, DM-d 6 ): δ =.22 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 3.05 (dd, J = 7., 9.3 z, Н, Н а ); 3.32 (dd, J = 7., 3.6 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.58 (dd, J = 9.3, 3.6 z, Н, C); 6.92 (d, J = 7.6 z, 2 Н, Н o ); (m, Н, Н p ); (m, 2 Н, Н m ); 7.76 (d, J = 9.2 z, 2 Н, Н o ); 8.20 (d, J = 9.2 z, 2 Н, Н m ); 0.76 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.3 (СН 2 СН 3 ); 37.6, 38.9 (СН 2 ); 43.3 (C); 9.0, 20. (С o, С o ); 24.4 (С p ); 25. (С m ); 29.4 (С m ); 42.5, 44.8 (C i,p ); 48.3 (C i ); 54.6 (С=); 69.0, 73.6 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 9.9, 3.8 z, Н, C); (2-(4-Chlorophenyl)imino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)--(4-methoxyphenyl)- acetamide (5da). Colorless crystals, yield 260 mg (62%), mp C. Cl Н MR (300 Мz, CDCl 3 ): δ =.30 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.80 (dd, J = 6.2, 9.9 z, Н, Н а ); 3.34 (dd, J = 6.2, 3.8 z, Н, b ); 3.78 (s, 3 Н, ОC 3 ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 9.9, 3.8 z, Н, C); 6.82 (d, J = 8.9 z, 2 Н, m ); 6.90 (d, J = 8.6 z, 2 Н, o ); 7.27 (d, J = 8.6 z, 2 Н, Н m ); 7.35 (d, J = 8.9 z, 2 Н, Н o ); 7.52 (br s, Н, ) ppm. F 2 Me 0

11 3 С MR (75 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 38.3, 40. (СН 2 ); 44.0 (C); 55.4 (C 3 ); 4.2 (С m ); 2.9, 22.5 (С o, С o ); 29.3 (С m ); 29.9, 30.2 (C p, C i ); 46.5 (C i ); 54.3 (С=); 56.7 (C p ); 66.7, 73.8 (С=О) ppm. RM (EI), m/z: calcd for C Cl 3 3 [M+] , found acetamide (5db). Pale beige crystals, yield 282 mg (70%), mp C. Cl Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.30 (s, 3, C 3 ); 2.8 (dd, J = 6.3, 9.9 z, Н, Н а ); 3.35 (dd, J = 6.3, 3.8 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.44 (dd, J = 9.9, 3.8 z, Н, C); 6.90 (d, J = 8.7 z, 2, o ); 7.0 (d, J = 8.2 z, 2, m ); (m, 4, m, o ); 7.38 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 20.8 (C 3 ); 38.3, 40.2 (СН 2 ); 43.9 (C); 20.0, 22.5 (С o, С o ); 29.3, 29.5 (С m, С m ); 29.9 (C p ); 34.4, 34.6 (C i,p ); 46.5 (C i ); 54.4 (С=); 66.8, 73.8 (С=О) ppm. Cl RM (EI), m/z: calcd for [M+a] , found (2-(4-Chlorophenyl)imino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide Pale yellow crystals, yield 27 mg (70%), mp 2-23 C. (5dc). Н MR (400 Мz, DM-d 6 ): δ =.2 (t, J = 6.9 z, 3 Н, C 2 C 3 ); 2.95 (dd, J = 6.8, 9.4 z, Н, Н а ); 3.26 (dd, J = 6.8, 3.4 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.55 (dd, J = 9.4, 3.4 z, Н, C); 6.92 (d, J = 7.9 z, 2 Н, Н o ); (m, Н, Н p ); (m, 4 Н, Н m, Н m ); 7.55 (d, J = 7.9 z, 2 Н, Н o ); 0.25 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.4, 39.5 (СН 2 ); 43.4 (C); 20.6, 2.0 (С o, С o ); 24. (С p ); 26.9 (С p ); 28.2, 29.2 (С m, С m ); 37.6 (C i ); 48.2 (C i ); 54.5 (С=); 67.9, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C 9 8 Cl 3 2 [M+] , found (2-(4-Chlorophenyl)imino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)--(4-methylphenyl)- -(4-Chlorophenyl)-2-(2-(4-chlorophenyl)imino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)- acetamide (5dd). Colorless crystals, yield 340 mg (8%), mp C. Cl Cl Н MR (400 Мz, DM-d 6 ): δ =.20 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.97 (dd, J = 6.8, 9.4 z, Н, Н а ); 3.25 (dd, J = 6.8, 3.7 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.57 (dd, J = 9.4, 3.7 z, Н, C); 6.95 (d, J = 8.5 z, 2 Н, Н o ); 7.34 (d, J = 8.8 z, 2 Н, Н m ); 7.38 (d, J = 8.5 z, 2 Н, Н m ); 7.54 (d, J = 8.8 z, 2 Н, Н o ); 0.26 (br s, Н, ) ppm.

12 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.4, 38.5 (СН 2 ); 43.5 (C); 20.6, 22.9 (С o, С o ); 26.9, 28.2 (С p, С p ); 28.7, 29. (С m, С m ); 37.6 (C i ); 47. (C i ); 55.5 (С=); 67.9, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 Cl [M+] , found (2-(4-Chlorophenyl)imino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)--(4-fluorophenyl)acetamide (5de). Colorless crystals, yield 257 mg (63%), mp C. Cl Н MR (400 Мz, CDCl 3 ): δ =.29 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.82 (dd, J = 6.3, 9.8 z, Н, Н а ); 3.37 (dd, J = 6.3, 3.8 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 9.8, 3.8 z, Н, C); (m, 2 Н, o ); (m, 2 Н, m ); (m, 2 Н, m ); (m, 2 Н, o ); 7.70 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 38.3, 40.2 (СН 2 ); 43.8 (C); 5.7 (d, J = 22.7 z, С m ); 2. 8 (d, J = 8. z, С o ); 22.4 (С o ); 29.3 (С m ); 30.0 (C p ); 33.2 (d, J = 2.2 z, C i ); 46.5 (С i ); 54.2 (С=); 59.6 (d, J = z, С p ); 66.9, 73.8 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 ClF 3 2 [M+] , found (2-(4-Chlorophenyl)imino-3-ethyl-4-oxo-,3-thiazolidin-5-yl)--(4-nitrophenyl)acetamide (5df). Colorless crystals, yield 293 mg (68%), mp C. Cl Н MR (300 Мz, CDCl 3 ): δ =.3 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.93 (dd, J = 6.6, 9.3 z, Н,Н а ); 3.43 (dd, J = 6.6, 4. z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.46 (dd, J = 9.3, 4. z, Н, C); 6.89 (d, J = 8.4 z, 2 Н, o ); 7.29 (d, J = 8.4 z, 2 Н, m ); 7.68 (d, J = 8.8 z, 2 Н, Н o ); 8.9 (d, J = 8.8 z, 2 Н, Н m ); 8.3 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 38.5, 40.6 (СН 2 ); 43.5 (C); 9.2 (С o ); 22.4 (С o ); 25. (C m ); 29.4 (С m ); 30. (C p ); 43., 43.8 (C i,p ); 46.3 (С i ); 53.7 (С=); 67.5, 73.9 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 Cl 4 4 [M+] , found (3-Ethyl-2-(4-fluorophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methoxyphenyl)- acetamide (5ea). Colorless crystals, yield 290 mg (72%), mp C. F F 2 Me Н MR (400 Мz, DM-d 6 ): δ =.20 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.90 (dd, J = 7.7, 9.6 z, Н, Н а ); 3.22 (dd, J = 7.7, 3.4 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.54 (dd, J = 9.6, 3.4 z, Н, C); 6.86 (d, J = 9.0 z, 2 Н, Н m ); (m, 2 Н, Н o ); (m, 2 Н, Н m ); 7.42 (d, J = 9.0 z, 2 Н, Н o ); 9.97 (br s, Н, ) ppm. 2

13 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.4, 38.5 (СН 2 ); 43.6 (C); 55. (C 3 ); 3.9 (С m ); 5.9 (d, J = 22.2 z, С m ); 20.6 (С o ); 22.6 (d, J = 8.4 z, С o ); 3.8 (C i ); 44.6 (d, J = 2.2 z, C i ); 55.3 (С=, C p ); 59.0 (d, J = z, С p ); 67., 73.6 (С=О) ppm. RM (EI), m/z: calcd for C F 3 3 [M+] , found (3-Ethyl-2-(4-fluorophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methylphenyl)acetamide (5eb). Colorless crystals, yield 289 mg (75%), mp C. F Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.2 z, 3 Н, C 2 C 3 ); 2.30 (s, 3, C 3 ); 2.8 (dd, J = 6.2, 0. z, Н, Н а ); 3.36 (dd, J = 6.2, 3.8 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 0., 3.8 z, Н, C); (m, 2, o ); (m, 2, m ); 7.0 (d, J = 8.2 z, 2, m ); 7.33 (d, J = 8.2 z, 2, o ); 7.43 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 20.8 (C 3 ); 38.3, 40.2 (СН 2 ); 43.9 (C); 5.9 (d, J = 22.0 z, С m ); 20.0 (С o ); 22.4 (d, J = 8. z, С o ); 29.5 (С m ); 34.4, 34.6 (C i,p ); 44.0 (d, J = 2.2 z, C i ); 54.3 (С=); 59.9 (d, J = z, С p ); 66.9, 73.8 (С=О) ppm. F RM (EI), m/z: calcd for [M+] , found (3-Ethyl-2-(4-fluorophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide Colorless crystals, yield 38 mg (86%), mp C. (5ec). Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.82 (dd, J = 6.3, 0.0 z, Н, Н а ); 3.37 (dd, J = 6.3, 3.7 z, Н, b ); 6.94 (m, 2 Н, o ); (m, 2 Н, m ); (m, Н, Н p ); (m, 2 Н, m ); 7.46 (d, J = 7.8 z, 2 Н, Н o ); 7.73 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 38.3, 40.4 (СН 2 ); 43.8 (C); 5.9 (d, J = 22.7 z, С m ); 9.9 (С o ); 22.4 (d, J = 8. z, С o ); 24.7 (С p ); 29. (С m ); 37.2 (C i ); 44.0 (d, J = 2.2 z, С i ); 54.2 (С=); 60.0 (d, J = z, С p ); 67.0, 73.8 (С=О) ppm. RM (EI), m/z: calcd for C 9 8 F 3 2 [M+] , found (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 0.0, 3.7 z, Н, C); (4-Chlorophenyl)-2-(3-ethyl-2-(4-fluorophenyl)imino-4-oxo-,3-thiazolidin-5-yl)- acetamide (5ed). Colorless crystals, yield 298 mg (73%), mp C. F Cl Н MR (400 Мz, CDCl 3 ): δ =.30 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.82 (dd, J = 6.3, 9.7 z, Н, Н а ); 3.35 (dd, J = 6.3, 4.0 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.42 (dd, J = 9.7, 4.0 z, Н, C); (m, 2 Н, o ), (m, 2Н, m ); 7.25 (d, J = 8.7 z, 2 Н, Н m ); 7.42 (d, J = 8.7 z, 2 Н, Н o ); 7.77 (br s, Н, ) ppm. 3

14 3 С MR (00 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 38.4, 40.4 (СН 2 ); 43.7 (C); 6.0 (d, J = 22.8 z, С m ); 2. (С o ); 22.4 (d, J = 8. z, С o ); 29. (С m ); 29.8 (C p ); 35.8 (C i ); 43.9 (d, J = 2.2 z, С i ); 53.9 (С=); 60.0 (d, J = z, C p ); 67.0, 73.8 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 ClF 3 2 [M+] , found (3-Ethyl-2-(4-fluorophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-fluorophenyl)acetamide (5ee). Colorless crystals, yield 276 mg (7%), mp C. F (br s, Н, ) ppm. Н MR (300 Мz, CDCl 3 ): δ =.29 (t, J = 7. z, 3 Н, C 2 C 3 ); 2.82 (dd, J = 6.3, 9.9 z, Н, Н а ); 3.36 (dd, J = 6.3, 3.9 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.43 (dd, J = 9.9, 3.9 z, Н, C); (m, 6, m,o, m ); (m, 2 Н, o ); С MR (75 Мz, CDCl 3 ): δ = 2.5 (СН 2 СН 3 ); 38.3, 40.2 (СН 2 ); 43.8 (C); 5.7 (d, J = 22.7 z, С m ), 6.0 (d, J = 22.7 z, С m ); 2.8 (d, J = 7.6 z, С o ); 22.4 (d, J = 8. z, С o ); 33.2 (d, J = 2.7 z, C i ); 43.9 (d, J = 2.6 z, С i ); 53.9 (С=); 59.6 (d, J = z, C p ), 60.0 (d, J = z, C p ); 67.0, 73.8 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 F [M+] , found (3-Ethyl-2-(4-fluorophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-nitrophenyl)-acetamide (5ef). eige crystals, yield 309 mg (74%), mp 2-23 C. F Н MR (400 Мz, DM-d 6 ): δ =.2 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 3.06 (dd, J = 7., 9.3 z, Н, Н а ); 3.33 (dd, J = 7., 3.7 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.59 (dd, J = 9.3, 3.7 z, Н, C); (m, 2 Н, Н o ); (m, 2 Н, Н m ); 7.77 (d, J = 9.3 z, 2 Н, Н o ); 8.20 (d, J = 9.3 z, 2 Н, Н m ); 0.74 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.5, 38.8 (СН 2 ); 43.2 (C); 5.9 (d, J = 22.6 z, С m ); 8.8 (С o ); 22.6 (d, J = 8.4 z, С o ); 25.0 (С m ); 42.3, 44.7 (C i,p ); 44.6 (d, J = 2.9 z, C i ); 55. (С=); 59.0 (d, J = z, С p ); 68.9, 73.4 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 F 4 4 [M+] , found (3-Ethyl-2-(4-nitrophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-methoxyphenyl)- acetamide (5fa). Pale yellow crystals, yield 55 mg (36%), mp C. 2 Н MR (400 Мz, DM-d 6 ): δ =.22 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 2.95 (dd, J = 6.6, 9.6 z, Н, Н а ); 3.24 (dd, J = 6.6, 3.7 z, Н, b ); 3.70 (s, 3 Н, ОC 3 ); (m, 2 Н, С 2 СН 3 ); 4.6 (dd, J = 9.6, 3.7 z, Н, C); 6.85 (d, J = 9.0 z, 2 Н, Н m ); 7.7 (d, J = 8.8 z, 2 Н, o ); 7.4 (d, J = 9.0 z, 2 Н, o ); 8.23 (d, J = 8.8 z, 2 Н, m ); 0.00 (s, Н, ) ppm. F 2 Me 4

15 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.5, 38.2 (СН 2 ); 44.0 (C); 55. (C 3 ); 3.9 (С m ); 20.6 (С o ); 22. (C o ); 25.2 (C m ); 3.8 (C i ); 43.7 (C p ); 54.6, 55.3, 56.8 (С=, C i, C p ); 67., 73.6 (С=О) ppm. 2 RM (EI), m/z: calcd for C [M+] , found (3-Ethyl-2-(4-nitrophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide Colorless crystals, yield 248 mg (62%), mp C. (5fc). Н MR (400 Мz, DM-d 6 ): δ =.22 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 3.00 (dd, J = 6.8, 9.6 z, Н, Н а ); 3.28 (dd, J = 6.8, 3.5 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.63 (dd, J = 9.6, 3.5 z, Н, C); 7.04 (t, J = 7.3 z, Н, Н p ); 7.7 (d, J = 8.8 z, 2 Н, Н o ); (m, 2 Н, Н m ); 7.5 (d, J = 7.9 z, 2 Н, Н o ); 8.23 (d, J = 8.8 z, 2 Н, Н m ); 0.3 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2. (СН 2 СН 3 ); 37.5, 38.3 (СН 2 ); 43.9 (C); 9. (С o ); 22. (C o ); 23.4 (С p ); 25.2 (C m ); 28.7 (С m ); 38. (C i ); 43.7 (C p ); 54.6, 56.7 (С=, C i ); 67.7, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (4-Chlorophenyl)-2-(3-ethyl-2-(4-nitrophenyl)imino-4-oxo-,3-thiazolidin-5-yl)-acetamide (5fd). Pale yellow crystals, yield 30 mg (72%), mp C. 2 Н MR (400 Мz, DM-d 6 ): δ =.22 (t, J = 7.0 z, 3 Н, C 2 C 3 ); 3.0 (dd, J = 6.9, 9.3 z, Н, Н а ); 3.27 (dd, J = 6.9, 3.5 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.63 (dd, J = 9.3, 3.5 z, Н, C); 7.6 (d, J = 8.8 z, 2 Н, Н o ); 7.34 (d, J = 8.8 z, 2 Н, Н m ); 7.54 (d, J = 8.8 z, 2 Н, Н o ); 8.23 (d, J = 8.8 z, 2 Н, Н m ); 0.28 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 2.2 (СН 2 СН 3 ); 37.5, 38.3 (СН 2 ); 43.8 (C); 20.6 (С o ); 22. (C o ); 25.2 (C m ); 27.0 (C p ); 28.7 (С m ); 37.6 (C i ); 43.7 (C p ); 54.6, 56.7 (С=, C i ); 67.9, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 Cl 4 4 [M+] , found (3-Ethyl-2-(4-nitrophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-fluorophenyl)acetamide (5fe). Colorless crystals, yield 324 mg (78%), mp C. 2 (d, J = 8.7 z, 2 Н, Н m ); 0.20 (br s, Н, ) ppm. Cl F Н MR (400 Мz, DM-d 6 ): δ =.22 (t, J = 6.8 z, 3 Н, C 2 C 3 ); 3.00 (dd, J = 6.8, 9.4 z, Н, Н а ); 3.28 (dd, J = 6.8, 3.2 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.62 (dd, J = 9.4, 3.2 z, Н, C); (m, 4 Н, o, Н m ); (m, 2 Н, Н o );

16 3 С MR (00 Мz, DM-d 6 ): δ = 2. (СН 2 СН 3 ); 37.2, 38.2 (СН 2 ); 43.9 (C); 5. (d, J = 22.0 z, С m ); 20.9 (d, J = 8. z, С o ); 22. (C o ); 25.2 (С m ); 35.0 (d, J = 2.3 z, C i ); 43.7 (C p ); 54.6, 56.7 (С=, C i ); 58.0 (d, J = z, C p ); 67.6, 73.5 (С=О) ppm. RM (EI), m/z: calcd for C 9 7 F 4 4 [M+] , found (3-Ethyl-2-(4-nitrophenyl)imino-4-oxo-,3-thiazolidin-5-yl)--(4-nitrophenyl)acetamide (5ff). Yellow crystals, yield 307 mg (69%), mp C. 2 Н, Н o ); (m, 4 Н, Н m, Н m ); 0.75 (s, Н, ) ppm. Н MR (400 Мz, DM-d 6 ): δ =.23 (t, J = 6.9 z, 3 Н, C 2 C 3 ); 3. (dd, J = 7., 9.2 z, Н, Н а ); 3.36 (dd, J = 7., 3.4 z, Н, b ); (m, 2 Н, С 2 СН 3 ); 4.66 (dd, J = 9.2, 3.4 z, Н, C); 7.7 (d, J = 8.8 z, 2 Н, Н o ); 7.76 (d, J = 9.2 z, 2 3 С MR (00 Мz, DM-d 6 ): δ = 2. (СН 2 СН 3 ); 37.6, 38.5 (СН 2 ); 43.6 (C); 8.8 (С o ); 22. (С o ); 25.0, 25.2 (С m, С m ); 42.3, 43.7, 44.7 (C p, C i,p ); 54.5, 56.6 (С=, C i ); 68.9, 73.4 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (2-(2,6-Dimethylphenyl)imino-3-methyl-4-oxo-,3-thiazolidin-5-yl)--(4-methoxyphenyl)acetamide (5ga). eige crystals, yield 26 mg (66%), mp C. Н MR (400 Мz, CDCl 3 ): δ = 2.09 (s, 6 Н, 2 C 3 ); 2.83 (dd, J = 6.2, 9.2 z, Н, Н а ); 3.25 (dd, J = 6.2, 3.8 z, Н, b ); 3.39 (s, 3 Н, C 3 ); 3.76 (s, 3 Н, C 3 ); 4.40 (dd, J = 9.2, 3.8 z, Н, C); 6.8 (d, J = 8.9 z, 2 Н, Н m ); 6.92 (t, J = 7.4 z, Н, p ); 7.0 (d, J = 7.4 z, 2 Н, Н m ); 7.33 (d, J = 8.9 z, 2 Н, o ); 7.52 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 7.7 (2 C 3 ); 29.6 (СН 3 ); 40.4 (С 2 ); 43.9 (C); 55.4 (СН 3 ); 4. (С m ); 2.8 (С o ); 24. (C p ); (С o ); 28.3 (С m ); 30.3 (C i ); 45.5 (C i ); 54. (С=); 56.6 (C p ); 66.7, 74.2 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (2-(2,6-Dimethylphenyl)imino-3-methyl-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide (5gc). Pale pink crystals, yield 274 mg (75%), mp C. Н MR (400 Мz, CDCl 3 ): δ = 2.0 (s, 6 Н, 2 C 3 ); 2.86 (dd, J = 6.3, 9.3 z, Н, Н а ); 3.28 (dd, J = 6.3, 3.8 z, Н, b ); 3.40 (s, 3 Н, C 3 ); 4.4 (dd, J = 9.3, 3.8 z, Н, C); 6.92 (t, J = 7.4 z, Н, p ); 7.0 (d, J = 7.4 z, 2 Н, Н m ); (m, Н, Н p ); (m, 2 Н, m ); 7.44 (d, J = 7.6 z, 2 Н, Н o ); 7.65 (br s, Н, ) ppm. Me 2 6

17 3 С MR (00 Мz, CDCl 3 ): δ = 7.7 (2 C 3 ); 29.5 (СН 3 ); 40.3 (С 2 ); 44.0 (C); 9.8 (С o ); 24.2, 24.7 (С p, С p ); 28.0 (C o ); 28.2 (С m ); 29.0 (С m ); 37.2 (C i ); 45.4 (C i ); 54. (С=); 66.9, 74.2 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found yl)acetamide (5gd). Colorless crystals, yield 287 mg (7%), mp C. Н MR (300 Мz, CDCl 3 ): δ = 2.09 (s, 6 Н, 2 C 3 ); 2.87 (dd, J = 6.3, 9.0 z, Н, Н а ); 3.27 (dd, J = 6.3, 4.0 z, Н, b ); 3.40 (s, 3 Н, C 3 ); 4.4 (dd, J = 9.0, 4.0 z, Н, C); 6.93 (t, J = 7.4 z, Н, p ); 7.0 (d, J = 7.4 z, 2 Н, Н m ); 7.25 (d, J = 8.7 z, 2 Н, Н m ); 7.40 (d, J = 8.7 z, 2 Н, o ); 7.7 (br s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 7.7 (2 C 3 ); 29.6 (СН 3 ); 40.4 (С 2 ); 43.9 (C); 2. (С o ); 24.2 (C p ); 28.0 (C o ); 28.2 (С m ); 29.0 (C m ); 29.7 (C p ); 35.8 (C i ); 45.4 (C i ); 53.9 (С=); 66.9, 74.2 (С=О) ppm. RM (EI), m/z: calcd for C Cl 3 2 [M+] , found acetamide (5ge). Colorless crystals, yield 253 mg (66%), mp C. m ); (m, 2 Н, o ); 7.42 (br s, Н, ) ppm. Н MR (300 Мz, CDCl 3 ): δ = 2.09 (s, 6 Н, 2 С 3 ); 2.86 (dd, J = 6.3, 9.3 z, Н, Н а ); 3.28 (dd, J = 6.3, 3.7 z, Н, b ); 3.40 (s, 3 Н, С 3 ); 4.40 (dd, J = 9.3, 3.7 z, Н, C); (m, 5 Н, m,p, 3 С MR (75 Мz, CDCl 3 ): δ = 7.7 (2 C 3 ); 29.6 (СН 3 ); 40.2 (С 2 ); 43.9 (C); 5.7 (d, J = 22.7 z, С m ); 2.7 (d, J = 8. z, С o ); 24.2 (C p ); 28.0 (C o ); 28.2 (С m ); 33.2 (d, J = 2.8 z, C i ); 45.4 (C i ); 53.9 (С=); 59.5 (d, J = z, C p ); 66.9, 74.2 (С=О) ppm. RM (EI), m/z: calcd for C F 3 2 [M+] , found (4-Chlorophenyl)-2-(2-(2,6-dimethylphenyl)imino-3-methyl-4-oxo-,3-thiazolidin-5-2-(2-(2,6-Dimethylphenyl)imino-3-methyl-4-oxo-,3-thiazolidin-5-yl)--(4-fluorophenyl)- 2-(2-(2,6-Dimethylphenyl)imino-3-methyl-4-oxo-,3-thiazolidin-5-yl)--(4-nitrophenyl)- acetamide (5gf). Pale yellow crystals, yield 333 mg (8%), mp C. Н MR (400 Мz, CDCl 3 ): δ = 2.09 (s, 6 Н, 2 C 3 ); 2.96 (dd, J = 6.6, 8.6 z, Н, Н а ); 3.35 (dd, J = 6.6, 4.2 z, Н, b ); 3.42 (s, 3 Н, C 3 ); 4.45 (dd, J = 8.6, 4.2 z, Н, C); 6.94 (t, J = 7.4 z, Н, С p ); 7.0 (d, J = 7.4 z, 2 Н, Н m ); 7.66 (d, J = 9. z, 2 Н, Н o ); 8.5 (br s, Н, ); 8.9 (d, J = 9. z, 2 Н, m ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 7.7 (2 C 3 ); 29.7 (СН 3 ); 40.6 (С 2 ); 43.6 (C); 9. (С o ); 24.3 (C p ); 25. (С m ); 28.0 (C o ); 28.2 (C m ); 43.2, 43.7, 45.3 (C i, C i,p ); 53.5 (С=); 67.5, 74.2 (С=О) ppm. Cl F 2 7

18 RM (EI), m/z: calcd for C [M+] , found Reaction of thioureas 3h,i with -phenylmaleimide (4c). tirred mixture of -alkyl-ꞌphenylthiourea 3h or 3i ( mmol) and -phenylmaleimide (4c) (73 mg, mmol) in i-pr (5 ml) was refluxed for indicated time (7 h for 3h, 28 h for 3i). olvent was evaporated under reduced pressure and the residue was separated by column chromatography (hexane/etc 6:) to obtain thiazolidines 6h,7h and 6i,7i, respectively. 2-(3-Isopropyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--phenylacetamide (6h). Pale beige crystals, yield 93 mg (25%), mp C. Н MR (400 Мz, CDCl 3 ): δ =.53 (d, J = 7.0 z, 3 Н, C 3 );.54 (d, J = 7.0 z, 3 Н, C 3 ); 2.80 (dd, J = 6.0, 9.5 z, Н, Н а ); 3.32 (dd, J = 6.0, 4. z, Н, b ); 4.37 (dd, J = 9.5, 4. z, Н, C); 4.90 (sept, J = 7.0 z, Н, C(C 3 ) 2 ); 6.94 (d, J = 7.3 z, 2 Н, o ); (m, 2 Н, p, p ); (m, 4 Н, Н m, Н m ); (m, 3 Н, o, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 8.8 (2 C 3 ); 40.7 (С 2 ); 43.3 (C); 48.0 (C); 9.9, 20.9 (С o, С o ); 24.6, 24.7 (С p, С p ); 29.0, 29.3 (С m, С m ); 37.3 (C i ); 48.2 (C i ); 53.4 (С=); 67.0, 74.2 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (2-Isopropylimino-4-oxo-3-phenyl-,3-thiazolidin-5-yl)--phenylacetamide (7h). Colorless crystals, 42 mg (39%), mp C (decomp.). Н MR (400 Мz, CDCl 3 ): δ =.09 (d, J = 6. z, 3 Н, C 3 );.0 (d, J = 6. z, 3 Н, C 3 ); 2.94 (dd, J = 6.2, 9.8 z, Н, Н а ); 3.45 (dd, J = 6.2, 4.0 z, Н, b ); 3.49 (sept, J = 6. z, Н, C(C 3 ) 2 ); 4.60 (dd, J = 9.8, 4.0 z, Н, C); 7.08 (m, 2 Н, р ); (m, 4 Н, o, Н m ); (m,, р ); (m, 4 Н, Н m, Н o ); 7.72 (br s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 23.38, 23.4 (2 C 3 ); 39. (С 2 ); 43. (C); 52.9 (C); 9. (С o ); 23.4 (С p ); 28.0 (С p ); 28.4, 28.7, 29.8 (C m,o, С m ); 35.8 (C i ); 38.7 (C i ); 50.4 (С=); 67.8, 73.4 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (3-Cyclohexyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)--phenylacetamide (6i). Colorless crystals, yield 75 mg (8%), mp C (decomp.). Н MR (400 Мz, CDCl 3 ): δ = (m, 3 Н, с-ex); (m, 5 Н, c-ex); (m, 2, c-ex); 2.79 (dd, J = 6.2, 9.6 z, Н, Н а ); 3.33 (dd, J = 6.2, 4.0 z, Н, b ); 4.37 (dd, J = 9.6, 4.0 z, Н, C); (m, Н, C); 6.93 (d, J = 7.4 z, 2 Н, o ); (m, 2 Н, p, p ); (m, 4 Н, m, m ); (m, 3 Н, o, ) ppm. 8

19 3 С MR (00 Мz, CDCl 3 ): δ = 25., 26.0, 28., 28.2 (c-ex); 40.7 (С 2 ); 43.2 (C); 56.0 (C); 9.9, 20.9 (C o, C o ); 24.5, 24.6 (C p, C p ); 29.0, 29.2 (C m, C m ); 37.3 (C i ); 48.3 (C i ); 53.8 (С=); 67., 74.4 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (2-Cyclohexylimino-4-oxo-3-phenyl-,3-thiazolidin-5-yl)--phenylacetamide (7i). Colorless crystals, yield 45 mg (36%), mp C (decomp.). Н MR (400 Мz, CDCl 3 ): δ =.4-.9 (m,, с-ex); (m, 4 Н, с-ex); (m,, c-ex); (m, 4 Н, c-ex); 2.93 (dd, J = 6.2, 0.0 z, Н, Н а ); (m, Н, C); 3.45 (dd, J = 6.2, 3.8 z, Н, b ); 4.60 (dd, J = 0.0, 3.8 z, Н, C); (m, Н, р ); (m, 4 Н, Н o, Н m ); (m,, р ); (m, 4, Н m, Н o ); 7.80 (br s, Н, ) ppm. Н MR (400 Мz, DM-d 6 ): δ = (m, 5, с-ex); (m, 5, c-ex); (m, 2, Н а, C); 3.32 (dd, J = 6.5, 3.7 z, Н, b ); 4.70 (dd, J = 9.0, 3.7 z, Н, C); (m, Н, р ); (m, 4 Н, Н o, Н m ); (m,, р ); (m, 2, Н m ); 7.6 (d, J = 7.9 z, 2 Н, o ); 0.2 (s, Н, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 24.5, 25.5, 29.7, 33., 33.2 (c-ex); 40.8 (С 2 ); 43.6 (C); 6.7 (C); 9.8 (С o ), 24.4 (С p ); 28.5 (С p ); 28.0, 28.9, 29.0 (C m,o, С m ); 35. (C i ); 37.5 (C i ); 49.2 (С=); 67.3, 74. (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (2-tert-utylimino-4-oxo-3-phenyl-,3-thiazolidin-5-yl)--phenylacetamide (7j). Reaction of thiourea 3j with -phenylmaleimide (4c). tirred mixture of -tert-butyl-ꞌ-phenylthiourea (3j) (decomp.). (208 mg, mmol) and -phenylmaleimide (4c) (73 mg, mmol) in benzene (5 ml) was refluxed for 25 h. olvent was evaporated under reduced pressure and the residue was separated by column chromatography (hexane/etc 8:). Colorless crystals, yield 208 mg (55%), mp C Н MR (400 Мz, DM-d 6 ): δ =.8 (s, 9, (C 3 ) 3 ); 3.05 (dd, J = 6.4, 9.0 z, Н, a ); 3.29 (dd, J = 6.4, 3.7 z, Н, b ); 4.68 (dd, J = 9.0, 3.7 z, Н, C); (m, Н, р ); 7.24 (d, J = 7.2 z, 2 Н, o ); (m, 3 Н, p, Н m ); (m, 2, m ); 7.6 (d, J = 7.8 z, 2 Н, o ); 0.2 (s, Н, ) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 29.2 (3 C 3 ); 39.3 (С 2 ); 43.9 (C); 53.9 (C(C 3 ) 3 ); 9.2 (С o ), 23.4 (С p ); 27.7 (С p ); 28.4, 28.6, 28.8 (C m,o, С m ); 36.3 (C i ); 38.8 (C i ); 46.3 (С=); 67.8, 72.5 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found

20 2-(3-Ethyl-2-isopropylimino-4-oxo-,3-thiazolidin-5-yl)--phenylacetamide (7k). Reaction of thiourea 3k with -phenylmaleimide (4c). tirred mixture of -ethyl-ꞌisopropylthiourea (3k) (46 mg, mmol) and -phenylmaleimide (4c) (73 mg, mmol) in isopropyl alcohol (5 ml) was refluxed for 5 h. olvent was evaporated under reduced pressure and the residue was recrystallized from ethanol/water (:) mixture. Colorless crystals, yield 264 mg (83%), mp C. Н MR (400 Мz, CDCl 3 ): δ = (m, 9, 3 C 3 ); 2.78 (dd, J = 6.0, 9.7 z,, a ); 3.39 (dd, J = 6.0, 4.0 z,, b ); 3.45 (sept, J = 6.2 z,, C(C 3 ) 2 ); (m, 2, C 2 ); 4.43 (dd, J = 9.7, 4.0 z,, C); (m,, p ); (m, 2, m ); 7.5 (d, J = 7.7 z, 2, o ); 7.8 (br s,, ) ppm. 3 С MR (00 Мz, CDCl 3 ): δ = 2.4 (C 2 C 3 ); 23.50, (C(C 3 ) 2 ); 37.9, 4.0 (2 C 2 ); 43.5 (C); 53.5 (C(C 3 ) 2 ); 9.9 (C o ); 24.6 (C p ); 29.0 (C m ); 37.5 (C i ); 48.2 (C=); 67.4, 73.8 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found General procedure for the preparation of thiazolidinylacetic acids 9h,i,l. The stirred mixture of thiourea 3h,i,l ( mmol) and maleic anhydride (8) (98 mg, mmol) in benzene (5 ml) was refluxed for the indicated amount of time. The solvent was evaporated under reduced pressure and the residue was recrystallized from CCl 4 /i-pr mixture. 2-(3-Isopropyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)acetic acid (9h). During 2 h. Colorless crystals, yield 207 mg (7%), mp C. Н MR (400 Мz, DM-d 6 ): δ =.42 (d, J = 6.8 z, 3, C 3 );.44 (d, J = 6.8 z, 3, C 3 ); 2.88 (dd, J = 7.6, 8.4 z, Н, a ); 2.99 (dd, J = 7.6, 3.9 z, Н, b ); 4.40 (dd, J = 8.4, 3.9 z, Н, C); 4.75 (sept, J = 6.8 z,, C); 6.90 (d, J = 7.4 z, 2, o ); 7.2 (t, J = 7.4 z,, p ); (m, 2, m ); 2.7 (br s,, C) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 8.3 (СН 3 ); 8.5 (СН 3 ); 36.7 (СН 2 ); 42.6 (C); 46.9 (C); 20.9 (С o ); 24. (C p ); 29.2 (C m ); 48.4 (C i ); 54.3 (С=); 7.5 (С=О); 73.6 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (3-Cyclohexyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)acetic acid (9i). During 2 h. C C Colorless crystals, yield 290 mg (87%), mp C. Н MR (400 Мz, DM-d 6 ): δ =.0-.7 (m, Н, с-ex); (m, 2 Н, с-ex); (m, 3 Н, c-ex); (m, 2 Н, c-ex); (m, 2, c-ex); 2.86 (dd, J = 7.5, 8.4 z, Н, Н а ); 2.99 (dd, J = 7.5, 3.6 z, Н, b ); (m, 2, C, C); 6.88 (d, J = 7.8 z, 2, o ); (m,, p ); (m, 2, m ); 2.7 (br s,, C) ppm. 20

21 3 С MR (00 Мz, DM-d 6 ): δ = 24.5 (c-ex-c 2 ); 25.6 (c-ex-c 2 ); 25.7 (c-ex-c 2 ); 27.6 (c-ex-c 2 ); 27.7 (c-ex-c 2 ); 36.8 (СН 2 ); 42.6 (C); 54.9 (C); 20.9 (С o ); 24. (C p ); 29.2 (C m ); 48.5 (C i ); 54.6 (С=); 7.5 (С=О); 73.7 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found (3-enzyl-4-oxo-2-phenylimino-,3-thiazolidin-5-yl)acetic acid (9l). During 2 h. Colorless C crystals, yield 258 mg (76%), mp C. Н MR (400 Мz, DM-d 6 ): δ = 2.94 (dd, J = 7.6, 8.8 z, Н, a ); 3.08 (dd, J = 7.6, 3.8 z, Н, b ); 4.62 (dd, J = 8.8, 3.8 z, Н, C); 4.90 (d, J = 5.0 z,, C 2 ); 4.97 (d, J = 5.0 z,, C 2 ); 6.88 (d, J = 7.5 z, 2, o ); 7. (t, J = 7.5 z,, p ); (m,, p ); (m, 6, m,o, m ); 2.8 (br s,, C) ppm. 3 С MR (00 Мz, DM-d 6 ): δ = 36.5 (СН 2 C); 43.3 (C); 45.5 (СН 2 ); 20.9 (C o ); 24.3 (C p ); 27.3 (C p ); 27.5, 28.4 (C m,o ); 29.3 (C m ); 36. (C i ); 47.9 (C i ); 54.4 (C=); 7.6 (С=О); 73.6 (С=О) ppm. RM (EI), m/z: calcd for C [M+] , found Reaction of thiourea 3k with maleic anhydride (8). The stirred mixture of thiourea 3k (46 mg, mmol) and maleic anhydride (8) (98 mg, mmol) in benzene (5 ml) was C 9k- C 0k- refluxed for 5 h. The solvent was evaporated under reduced pressure and the residue was washed with a small portion of cold benzene. Mixture of two isomers 2-(2-ethylimino-3-isopropyl-4-oxo-,3-thiazolidin-5-yl)acetic acid (9k-) and (2-(3-ethyl-2-isopropylimino-4-oxo-,3-thiazolidin-5-yl)acetic acid (0k-) in the ratio :.8 was obtained. Colorless solid, yield 220 mg (90%). Н MR (400 Мz, DM-d 6 ) of isomer 9k-: δ =.6 (t, J = 7.2 z, 3, C 2 C 3 );.3 (d, J = 6.9 z, 3, C(C 3 ));.33 (d, J = 6.9 z, 3, C(C 3 )); 2.82 (dd, J = 7.5, 8.5 z,, a ); 2.99 (dd, J = 7.5, 3.8 z,, b ); 3.9 (q, J = 7.2 z, 2, C 2 C 3 ); 4.35 (dd, J = 8.5, 3.8 z,, C); 4.62 (sept, J = 6.9 z,, C(C 3 )); 2.7 (br s,, C) ppm. Н MR (400 Мz, DM-d 6 ) of isomer 0k-: δ =.06 (t, J = 7.0 z, 3, C 2 C 3 );.0 (d, J = 6.2 z, 3, C(C 3 ));. (d, J = 6.2 z, 3, C(C 3 )); 2.83 (dd, J = 7.5, 8.9 z,, a ); 3.04 (dd, J = 7.5, 3.8 z,, b ); 3.38 (sept, J = 6.2 z,, C(C 3 )); (m, 2, C 2 C 3 ); 4.43 (dd, J = 8.9, 3.8 z,, C); 2.7 (br s,, C) ppm. 3 С MR (00 Мz, DM-d 6 ) of isomer 9k-: δ = 5.8 (C 2 C 3 ); 8.3, 8.4 (C(C 3 ) 2 ); 37. (C 2 C); 42.4 (C); 46.2 (C 2 C 3 ); 46.3 (C(C 3 ) 2 ); 49.0 (C=); 7.5 (C=); 73. (C=) ppm. 2

22 3 С MR (00 Мz, DM-d 6 ) of isomer 0k-: δ = 2.0 (C 2 C 3 ); 23.57, (C(C 3 ) 2 ); 37.0, 37. (2 C 2 ); 42.9 (C); 52.7 (C(C 3 ) 2 ); 50.7 (C=); 7.6 (C=); 72.8 (C=) ppm. RM (EI), m/z: calcd for C [M+] , found

23 Me 5aa Et Me 23

24 Me 5ab Et 24

25 Me 5ac Et 25

26 Me 5ad Et Cl 26

27 Me 5ae Et F 27

28 Me 5af Et 2 28

29 5ba Et Me 29

30 5bb Et 30

31 5bc Et 3

32 5bd Et Cl 32

33 5be Et F 33

34 5bf Et 2 34

35 5bg Et C 2 Et 35

36 5ca Et Me 36

37 5cb Et 37

38 5cc Et 38

39 5cd Et Cl 39

40 5ce Et F 40

41 5cf Et 2 4

42 Cl 5da Et Me 42

43 Cl 5db Et 43

44 Cl 5dc Et 44

45 Cl 5dd Et Cl 45

46 Cl 5de Et F 46

47 Cl 5df Et 2 47

48 F 5ea Et Me 48

49 F 5eb Et 49

50 F 5ec Et 50

51 F 5ed Et Cl 5

52 F 5ee Et F 52

53 F 5ef Et 2 53

54 2 5fa Et Me 54

55 2 5fc Et 55

56 2 5fd Et Cl 56

57 2 5fe Et F 57

58 2 5ff Et 2 58

59 5ga Me 59

60 5gc 60

61 5gd Cl 6

62 5ge F 62

63 5gf 2 63

64 6h 64

65 6i 65

66 7h 66

67 7i 67

68 7j 68

69 7k 69

70 9h C 70

71 9i C 7

72 C 9k :.8 0k C 72

73 C 9l 73

74 6h 7h 74

75 6i 7i 75

76 9i C 76

77 G. M. heldrick, cta Cryst. 2008, 64, V. Dolomanov, L. J. ourhis, R. J. Gildea, J.. K. oward,. Puschmann, LEX2: complete structure solution, refinement and analysis program, J. ppl. Cryst. 2009, 42, CryslisPro, gilent Technologies, Version (release ). 4 K. Inamoto, C. asegawa, J. Kawasaki, K. iroya, T. Doi, dv. ynth. Catal. 200, 352, L. Doub, L. M. Richardson, D. R. erbst, M. L. lack,. L. tevenson, L. L. ambas, G. P. Youmans,.. Youmans, J. m. Chem. oc. 958, 80, J.. Davis, F.. Dains, J. m. Chem. oc. 935, 57, G.. Jin, da Y. Lee, Y.-J. Cheon,. J. Gim, do. Kim,.-D. Kim, J.-. Ryu, R. Jeon, ioorg. Med. Chem. Lett. 2009, 9, W. Weith, Chem. er. 875, 8, T. Golding, I. X. assereddin, J. Chem. Res. Miniprint 98, M. L. Willard, M. Z. Jones J. m. Chem. oc. 940, 62, G. M. Dyson, J. Indian Chem. oc. 93, 8, G. Jonova, G. Vassilev, Pharmazie 978, 33, M. Fujita, Y. Inokuma, G.-. ing, ngew. Chem. Int. Ed. 202, 5, L.. chwartzman,.. Corson, J. m. Chem. oc. 954, 76, G. Vassilev, M. Koleva, M. Ilieva,. Galabov, J. Mol. truct. 982, 82, R.. Ragsdale,. R. Karstetter, R.. Drago, Inorg. Chem. 965, 4, P. K. Mohanta,. Dhar,. K. amal,. Ila,. Junjappa, Tetrahedron 2000, 56, D. J. eaver, D. P. Roman, P. J. toffel, J. m. Chem. oc. 957, 79, K. Goto,. Ikeda, T. Morita,. ishimura, T. ukamoto, K. Yoshiizumi, K. Yoshino, Chem. Pharm. ull. 996, 44,