Supporting Information
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting Information Iron(II) Bromide-Catalyzed Oxidative Coupling of Benzylamines with ortho-substituted Anilines: Synthesis of 1,3-Benzazoles Kovuru Gopalaiah * and Sankala Naga Chandrudu Department of Chemistry, University of Delhi, Delhi , India gopal@chemistry.du.ac.in Table of Contents Spectral Data for Compounds 3a-q. S2 Spectral Data for Compounds 5a-k. S6 Spectral Data for Compounds 7a-l.. S9 NMR Spectra for Compounds in Table 2...S12 NMR Spectra for Compounds in Table 3...S29 NMR Spectra for Compounds in Table 4...S40 NMR Spectra for Compound S52 NMR Spectra for Compound S53 HRMS Spectra for New Products...S54 GC-MS Spectra for Reaction of 1a with 2a...S68 References S80
2 2-Phenyl-1H-benzo[d]imidazole (3a): White solid (357 mg, 92%), mp C (lit C) 1 ; IR (KBr) 3437, 2924, 2626, 1741, 1444, 1409, 1275, 1119, 969, 738 cm -1 ; 1 H NMR (400 MHz, CD 3 OD) δ (m, 2H), (m, 5H), (m, 2H); 13 C NMR (100 MHz, CD 3 OD) δ 153.3, 131.3, 130.9, 130.1, 127.7, 123.9, (p-Tolyl)-1H-benzo[d]imidazole (3b): White solid (387 mg, 93%), mp C (lit C) 1 ; IR (KBr) 3435, 2853, 2364, 1426, 1272, 1225, 962, 820 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.02 (d, J = 8.4 Hz, 2H), (m, 2H), 7.32 (d, J = 7.6 Hz, 2H), 7.15 (br s, 2H), 2.34 (s, 3H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 151.4, 139.6, 129.5, 127.5, 126.4, (4-Methoxyphenyl)-1H-benzo[d]imidazole (3c): White solid (430 mg, 96%), mp C (lit C) 1 ; IR (KBr) 3448, 3055, 2926, 1742, 1611, 1454, 1436, 1371, 1254, 1179, 1034, 745 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ (m, 2H), 7.55 (br s, 2H), (m, 4H), 3.82 (s, 3H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 160.6, 151.4, 128.0, 122.7, 121.8, 114.4, (4-Fluorophenyl)-1H-benzo[d]imidazole (3d): White solid (369 mg, 87%), mp C (lit. 248 C) 2 ; IR (KBr) 3445, 3053, 2920, 2855, 1604, 1498, 1452, 1374, 1320, 1277, 1229, 968, 838, 748 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ (m, 2H), 7.64 (d, J = 7.2 Hz, 1H), 7.51 (d, J = 7.6 Hz, 1H), (m, 2H), (m, 2H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 164.3, 161.9, 150.4, 143.8, 135.0, 128.8, 128.7, 122.6, 121.8, 118.9, 116.2, 115.9, (2-Chlorophenyl)-1H-benzo[d]imidazole (3e): White solid (369 mg, 81%), mp C (lit C) 3 ; IR (KBr) 3448, 3048, 2922, 2856, 2772, 1463, 1444, 1405, 1232, 1054, 973, 742 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ (m, 1H), (m, S2
3 3H), (m, 2H), (m, 2H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 149.1, 132.1, 131.7, 131.3, 130.4, 129.9, 127.5, (3,4-Dichlorophenyl)-1H-benzo[d]imidazole (3f): White solid (440 mg, 84%), mp C (lit o C) 3 ; IR (KBr) 3433, 3051, 2923, 2366, 1624, 1444, 1424, 1139, 1114, 1033, 821, 745 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.33 (s, 1H), 8.09 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 2H), 7.20 (br s, 2H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 149.0, 143.7, 135.1, 132.5, 132.0, 131.4, 130.7, 128.1, 126.6, 123.3, 122.3, 119.2, (3,5-Bis(trifluoromethyl)phenyl)-1H-benzo[d]imidazole (3g): White solid (528 mg, 80%), mp C; IR (KBr) 3429, 3067, 2928, 1624, 1420, 1352, 1283, 1131, 900, 766, 742 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.76 (s, 2H), 8.17 (s, 1H), 7.68 (d, J = 7.2 Hz, 1H), 7.56 (d, J = 8.0 Hz, 1H), (m, 2H); 13 C NMR (100 MHz, DMSOd 6 ) δ 148.2, 143.5, 135.1, 132.6, 131.6, 131.3, 130.9, 130.6, 127.3, 126.6, 124.6, 123.7, 122.9, 122.4, 121.9, 119.4, 111.9; HRMS (ESI) m/z calcd for C 15 H 8 F 6 N 2 [M + H] , found (Benzo[d][1,3]dioxol-5-yl)-1H-benzo[d]imidazole (3h): Pale brown solid (424 mg, 89%), mp C (lit C) 1 ; IR (KBr) 3432, 3050, 2924, 2630, 1618, 1469, 1228, 1038, 933, 741 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ (m, 2H), 7.61 (d, J = 7.2 Hz, 1H), 7.48 (d, J = 7.6 Hz, 1H), (m, 2H), 7.09 (d, J = 7.6 Hz, 1H), 6.12 (s, 2H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 151.1, 148.7, 147.8, 143.7, 134.9, 124.2, 122.3, 121.5, 120.8, 118.6, 111.1, 108.7, 106.4, (2-Methoxyphenyl)-1H-benzo[d]imidazole (3i): White solid (390 mg, 87%), mp C (lit C) 4 ; IR (KBr) 3453, 2964, 1603, 1584, 1474, 1438, 1245, 1091, 1023, 799, 747 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.16 (d, J = 7.2 Hz, 1H), 7.58 S3
4 (dd, J = 3.2, 5.6 Hz, 2H), 7.41 (t, J = 8.0 Hz, 1H), (m, 3H), 7.05 (t, J = 7.2 Hz, 1H), 3.91 (s, 3H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 157.6, 149.8, 138.8, 132.6, 130.4, 123.2, 121.9, 118.0, 115.8, 112.9, (Naphthalen-1-yl)-1H-benzo[d]imidazole (3j): White solid (405 mg, 83%), mp C (lit C) 5 ; IR (KBr) 3448, 3047, 2925, 2854, 1449, 1402, 1230, 1037, 805, 774, 749 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 9.09 (d, J = 8.4 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H), (m, 2H), (m, 5H), (m, 2H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 151.4, 133.6, 130.5, 130.2, 128.4, 127.9, 127.5, 126.4, 126.4, (Thiophen-2-yl)-1H-benzo[d]imidazole (3k): Pale yellow solid (324 mg, 81%), mp C (lit C) 1 ; IR (KBr) 3412, 2950, 1638, 1420, 1016, 743 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ (m, 1H), (m, 1H), 7.60 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 8.4 Hz, 1H), (m, 3H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 147.1, 143.6, 134.7, 133.7, 128.8, 128.3, 126.7, 122.7, 121.8, 118.6, (Pyridin-4-yl)-1H-benzo[d]imidazole (3l): White solid (254 mg, 65%), mp C (lit C) 6 ; IR (KBr) 3546, 3164, 2944, 2628, 2368, 2293, 2253, 1425, 1042, 919 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), 7.62 (br s, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 150.5, 148.7, 137.4, 123.9, n-Octyl-1H-benzo[d]imidazole (3m): White solid (315 mg, 73%), mp C (lit o C) 7 ; IR (KBr) 3442, 3054, 2927, 1542, 1424, 1272, 1029, 737 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 8H), 0.82 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 155.4, 138.4, 122.1, 114.5, 31.6, 29.3, 29.4, 29.3, 28.9, 28.3, 22.5, S4
5 6-Nitro-2-(p-tolyl)-1H-benzo[d]imidazole (3n): Yellow solid (400 mg, 79%), mp C; IR (KBr) 3254, 2925, 1492, 1343, 1064, 825, 740 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.16 (d, J = 2.4 Hz, 1H), (m, 1H), 7.75 (d, J = 8.0 Hz, 2H), 7.47 (d, J = 9.2 Hz, 1H), 7.13 (d, J = 8.0 Hz, 2H), 2.18 (s, 3H); 13 C NMR (100 MHz, DMSOd 6 ) δ 156.6, 143.8, 143.2, 142.0, 139.4, 130.4, 127.5, 126.2, 118.7, 115.1, 112.0, 21.6; HRMS (ESI) m/z calcd for C 14 H 11 N 3 O 2 [M + H] , found Methyl-2-(p-tolyl)-1H-benzo[d]imidazole (3o): White solid (364 mg, 82%), mp C (lit. 195 C) 2 ; IR (KBr) 3419, 2920, 1609, 1420, 1385, 1308, 1109, 965, 824, 729 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (d, J = 7.6 Hz, 2H), 7.48 (d, J = 8.4 Hz, 1H), 7.35 (s, 1H), 7.19 (d, J = 7.6 Hz, 2H), (m, 1H), 2.42 (s, 3H), 2.34 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 151.9, 140.2, 138.7, 137.6, 132.7, 129.7, 127.0, 126.6, 124.3, 115.0, 114.3, 21.6, (p-Tolyl)-1H-naphtho[2,3-d]imidazole (3p): Light yellow solid (392 mg, 76%), mp C; IR (KBr) 3452, 2918, 1607, 1465, 1429, 1264, 1121, 855, 824, 724 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.00 (d, J = 8.8 Hz, 3H), 7.89 (dd, J = 6.0, 3.6 Hz, 2H), (m, 4H), (m, 1H), 2.28 (s, 3H); 13 C NMR (100 MHz, DMSO-d 6 ) δ 156.6, 142.2, 137.8, 130.9, 130.7, 129.9, 129.5, 128.5, 127.9, 127.0, 124.7, 21.8; HRMS (ESI) m/z calcd for C 18 H 14 N 2 [M + H] , found (p-Tolyl)-3H-imidazo[4,5-b]pyridine (3q): White solid (334 mg, 80%), mp C (lit C) 8 ; IR (KBr) 3172, 2920, 1603, 1584, 1435, 1242, 1088, 1021, 745 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.24 (d, J = 4.0 Hz, 1H), (m, 3H), 7.28 (d, J = 8.0 Hz, 2H), 7.19 (dd, J = 8.0, 4.8 Hz, 1H), 2.27 (s, 3H); 13 C NMR (100 MHz, DMSOd 6 ) δ 144.6, 142.0, 130.6, 127.6, 126.9, 119.3, S5
6 5-Methyl-2-phenylbenzo[d]oxazole (5a): White solid (297 mg, 71%), mp C (lit C) 9 ; IR (KBr) 2923, 2364, 1553, 1477, 1448, 1265, 1200, 1055, 926, 797, 702 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 4H), 7.43 (d, J = 8.8 Hz, 1H), 7.14 (d, J = 8.4 Hz, 1H), 2.47 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 163.1, 148.9, 142.3, 134.3, 131.3, 128.8, 127.5, 127.3, 126.2, 119.9, 109.9, Methyl-2-(p-tolyl)benzo[d]oxazole (5b): White solid (330 mg, 74%), mp C (lit C) 9 ; IR (KBr) 2922, 2364, 1703, 1555, 1499, 1261, 1200, 1179, 1055, 795, 727 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.11 (d, J = 8.4 Hz, 2H), 7.52 (s, 1H), 7.41 (d, J = 8.8 Hz, 1H), 7.30 (d, J = 8.4 Hz, 2H), 7.12 (d, J = 8.4 Hz, 1H), 2.46 (s, 3H), 2.42 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 163.3, 148.9, 142.3, 141.9, 134.2, 129.8, 129.7, 129.6, 127.5, 125.9, 124.5, 119.7, 109.8, 21.6, (4-Methoxyphenyl)-5-methylbenzo[d]oxazole (5c): White solid (382 mg, 80%), mp C (lit C) 9 ; IR (KBr) 2923, 1606, 1500, 1255, 1176, 1021, 841, 805 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), 7.50 (s, 1H), 7.40 (d, J = 8.8 Hz, 1H), 7.10 (d, J = 7.6 Hz, 1H), (m, 2H), 3.87 (s, 3H), 2.46 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 162.2, 148.9, 142.4, 134.2, 131.9, 129.3, 125.7, 119.9, 119.5, 114.3, 109.7, 55.4, (4-Fluorophenyl)-5-methylbenzo[d]oxazole (5d): White solid (313 mg, 69%), mp C; IR (KBr) 2924, 2362, 1474, 1221, 1151, 1053, 845, 796 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), 7.56 (s, 1H), 7.45 (d, J = 8.0 Hz, 1H), (m, 3H), 2.51 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 165.9, 163.4, 162.2, 149.0, 142.3, 134.4, 129.8, 129.7, 126.2, 123.7, 123.6, 119.9, 116.2, 115.9, 109.9, 21.5; HRMS (ESI) m/z calcd for C 14 H 10 FNO [M + H] , found S6
7 2-(2-Chlorophenyl)-5-methylbenzo[d]oxazole (5e): White solid (316 mg, 65%), mp C; IR (KBr) 2922, 1570, 1474, 1264, 1234, 1197, 1087, 1029, 798, 732 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), 7.61 (s, 1H), (m, 1H), 7.46 (d, J = 8.0 Hz, 1H), (m, 2H), 7.18 (dd, J = 8.8, 1.2 Hz, 1H), 2.48 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 161.0, 148.9, 141.9, 134.5, 133.4, 131.8, 131.4, 126.9, 126.8, 126.4, 120.4, 110.1, 21.6; HRMS (ESI) m/z calcd for C 14 H 10 ClNO [M + H] , found (3,4-Dichlorophenyl)-5-methyl-benzo[d]oxazole (5f): White solid (371 mg, 67%), mp C; IR (KBr) 2372, 2068, 1639, 1466, 1378, 1065, 1029, 888, 808, 724 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), (m, 1H), 7.52 (s, 1H), 7.42 (d, J = 8.4Hz, 1H), 7.17 (d, J = 8.0 Hz, 1H), 2.47 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 160.9, 149.0, 142.0, 135.6, 134.8, 133.4, 130.9, 129.2, 127.2, 126.8, 126.4, 120.1, 110.0, 21.5; HRMS (ESI) m/z calcd for C 14 H 9 Cl 2 NO [M + H] , found (3,5-Bis(trifluoromethyl)phenyl)-5-methylbenzo[d]oxazole (5g): White solid (428 mg, 62%), mp C; IR (KBr) 2926, 1382, 1329, 1281, 1137, 905, 803, 744 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.68 (s, 2H), 8.00 (s, 1H), 7.59 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.25 (s, 1H), 2.50 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 160.0, 149.1, 141.8, 135.3, 132.8, 132.4, 129.4, 127.6, 127.4, 127.0, 124.5, 124.4, 124.4, 124.3, 121.6, 120.4, 118.8, 110.3, 21.5; HRMS (ESI) m/z calcd for C 16 H 9 F 6 NO [M + H] , found (Benzo[d][1,3]dioxol-5-yl)-5-methylbenzo[d]oxazole (5h): White solid (385 mg, 76%), mp C; IR (KBr) 2926, 1561, 1477, 1231, 1106, 1032, 928, 795 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), 7.66 (s, 1H), 7.49 (s, 1H), 7.38 (d, J = 8.0 Hz, S7
8 1H), (m, 1H), 6.91 (d, J = 8.0 Hz, 1H), 6.04 (s, 2H), 2.45 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 162.9, 150.4, 148.8, 148.1, 142.3, 134.2, 125.8, 122.6, 121.3, 119.6, 109.7, 108.6, 107.6, 101.7, 21.5; HRMS (ESI) m/z calcd for C 15 H 11 NO 3 [M + H] , found (2-Methoxyphenyl)-5-methylbenzo[d]oxazole (5i): White solid (349 mg, 73%), mp C; IR (KBr) 2923, 2042, 1601, 1465, 1266, 1196, 1024, 797, 754 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.20 (dd, J = 8.0, 2.0 Hz, 1H), 7.68 (t, J = 1.2 Hz, 1H), (m, 2H), 7.23 (d, J = 8.4 Hz, 1H), (m, 2H), 4.09 (s, 3H), 2.56 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 161.6, 158.4, 148.6, 142.3, 133.9, 132.6, 131.2, 125.9, 120.6, 120.0, 116.4, 112.0, 109.7, 56.1, 21.4; HRMS (ESI) m/z calcd for C 15 H 13 NO 2 [M + H] , found Methyl-2-(naphthalen-1-yl)benzo[d]oxazole (5j): White solid (368 mg, 71%), mp C; IR (KBr) 3053, 2922, 1690, 1541, 1254, 1181, 976, 799, 773 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 9.44 (d, J = 8.8 Hz, 1H), 8.40 (dd, J = 7.2, 0.8 Hz, 1H), (m, 1H), 7.93 (d, J = 8.0 Hz, 1H), (m, 2H), (m, 2H), 7.50 (d, J = 8.0 Hz, 1H), (m, 1H), 2.51 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 162.9, 148.4, 142.4, 134.2, 133.9, 132.1, 130.6, 129.2, 128.6, 127.8, 126.4, 124.9, 123.7, 120.1, 109.8, 21.5; HRMS (ESI) m/z calcd for C 18 H 13 NO [M + H] , found Methyl-2-(thiophen-2-yl)benzo[d]oxazole (5k): White solid (288 mg, 67%), mp C; IR (KBr) 3102, 2921, 1575, 1560, 1416, 1261, 1192, 1003, 853, 796, 716 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), 7.49 (s, 1H), (m, 1H), (m, 2H), 2.46 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 159.1, 148.6, 142.1, 134.5, 130.0, 129.7, 128.2, 126.1, 119.7, 109.7, HRMS (ESI) m/z calcd for C 12 H 9 NOS [M + H] , found S8
9 2-Phenylbenzo[d]thiazole (7a): White solid (329 mg, 78%), mp C (lit. 114 C) 2 ; IR (KBr) 3065, 1509, 1479, 1314, 1284, 1225, 963, 760, 668 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 3H), (m, 1H), (m, 4H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 168.1, 154.1, 135.0, 133.5, 130.9, 128.9, 127.5, 126.3, 125.2, 123.2, (p-Tolyl)benzo[d]thiazole (7b): White solid (360 mg, 80%), mp C (lit C) 2 ; IR (KBr) 3058, 2923, 1608, 1485, 1313, 1229, 962, 818, 760 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), 7.28 (d, J = 8.8 Hz, 2H), 2.4 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 168.2, 154.1, 141.4, 134.9, 130.8, 129.7, 127.4, 126.2, 125.0, 123.0, 121.5, (4-Methoxyphenyl)benzo[d]thiazole (7c): White solid (410 mg, 85%), mp C (lit C) 10 ; IR (KBr) 3064, 2940, 2364, 1605, 1483, 1310, 1258, 968, 832, 759 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 3H), 7.86 (d, J = 8.0Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 3.86 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.9, 161.9, 154.1, 134.8, 129.1, 126.3, 126.2, 124.8, 122.8, 121.5, 114.3, (4-Fluorophenyl)benzo[d]thiazole (7d): White solid (380 mg, 83%), mp C (lit C) 2 ; IR (KBr) 3075, 2925, 1482, 1228, 967, 836, 755, 729 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 3H), 7.88 (d, J = 7.20 Hz, 1H), (m, 1H), (m, 1H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 160.1, 153.8, 135.6, 135.1,132.7, 132.4, 127.3, 127.0, 126.2, 124.3, 124.0, 124.0, 124.0, 123.8, (2-Chlorophenyl)benzo[d]thiazole (7e): White solid (367 mg, 75%), mp C (lit C) 11 ; IR (KBr) 3069, 2921, 1428, 1271, 1221, 967, 756, 731 cm -1 ; 1 H NMR (400 S9
10 MHz, CDCl 3 ) δ (m, 1H), 8.12 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 2H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 164.1, 152.4, 136.0, 132.6, 132.2, 131.7, 131.1, 130.8, 127.1, 126.2, 125.4, 123.4, (3,4-Dichlorophenyl)benzo[d]thiazole (7f): White solid (407 mg, 73%), mp C; IR (KBr) 3054, 2923, 1373, 1229, 1026, 983, 823, 756 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.21 (s, 1H), 8.06 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 2H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 165.0, 153.8, 135.0, 135.0, 133.4, 130.9, 128.9, 126.6, 126.4, 125.7, 123.4, 121.6; HRMS (ESI) m/z calcd for C 13 H 7 Cl 2 NS [M + H] , found (3,5-Bis(trifluoromethyl)phenyl)benzo[d]thiazole (7g): White solid (465 mg, 67%), mp C; IR (KBr) 2924, 2853, 1539, 1377, 1287, 1135, 895, 760 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.49 (s, 2H), 8.10 (d, J = 8.4 Hz, 1H), 7.96 (s, 1H), 7.92 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 164.1, 153.8, 135.6, 135.1, 133.0, 132.7, 132.4, 132.0, 127.3, 127.0, 126.9, 126.2, 124.3, 124.0, 124.0, 124.0, 123.8, 121.8, 121.6; HRMS (ESI) m/z calcd for C 15 H 7 F 6 NS [M + H] , found (Benzo[d][1,3]dioxol-5-yl)benzo[d]thiazole (7h): White solid (388 mg, 76%), mp C (lit C) 10 ; IR (KBr) 3052, 2910, 1686, 1605, 1471, 1446, 1253, 1036, 936, 760 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.93 (d, J = 8.0 Hz, 1H), 7.77 (d, J = 7.2 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), 6.80 (d, J = 8 Hz, 1H), 5.95 (s, 2H); 13 CNMR (100 MHz, CDCl 3 ) δ 167.5, 153.9, 150.0, 148.3, 134.8, 127.9, 126.2, 124.9, 122.8, 122.4, 121.4, 108.6, 107.4, (2-Methoxyphenyl)benzo[d]thiazole (7i): White solid (347 mg, 72%), mp C (lit C) 11 ; IR (KBr) 3093, 2937, 1599, 1499, 1431, 1249, 1018, 755, 729 cm -1 ; S10
11 1 H NMR (400 MHz, CDCl 3 ) δ (m,1h), 8.10 (d, J = 8.0Hz, 1H), 7.91 (d, J = 8.0 Hz, 1H), (m, 2H), (m, 1H), 7.11 (t, J = 7.6 Hz, 1H), (m, 1H),4.02 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 163.1, 157.2, 152.1, 136.1, 131.7, 129.5, 125.8, 124.5, 122.7, 122.3, 121.1, 121.1, (Naphthalen-1-yl)benzo[d]thiazole (7j): White solid (392 mg, 75%), mp C; IR (KBr) 3058, 2926, 1507, 1435, 1229, 1100, 934, 801, 758 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.93 (d, J = 8.8 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), (m, 4H), (m, 4H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.6, 154.1, 135.4, 134.0, 131.0, 130.8, 130.6, 129.4, 128.4, 127.6, 126.5, 126.3, 125.8, 125.3, 125.0, 123.5, 121.4; HRMS (ESI) m/z calcd for C 17 H 11 NS [M + H] , found (Thiophen-2-yl)benzo[d]thiazole (7k): White solid (299 mg, 69%), mp C (lit C) 10 ; IR (KBr) 2102, 1639, 1542, 1477, 1456, 1436, 1416, 1355, 1312, 1259, 1233, 1224, 1164, 1076, 1051, 1012, 943, 912, 854, 828, 762, 730, 714 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.01 (d, J = 8.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 161.3, 153.6, 137.3, 134.6, 129.3, 128.6, 128.0, 126.4, 125.2, 122.9, (Pyridin-4-yl)benzo[d]thiazole (7l): Pale yellow solid (237 mg, 56%), mp C (lit C) 6 ; IR (KBr) 3054, 2924, 1600, 1476, 1408, 1313, 978, 820, 757 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.76 (d, J = 6.0 Hz, 2H), 8.12 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 6.4 Hz, 3H), 7.53 (t, J = 7.2 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 153.9, 150.6, 140.6, 135.2, 126.8, 126.2, 123.9, 121.9, S11
12 Figure S1. 1 H NMR of 3a (400 MHz, CD 3 OD) and 13 C NMR of 3a (100 MHz, CD 3 OD). S12
13 Figure S2. 1 H NMR of 3b (400 MHz, DMSO-d 6 ) and 13 C NMR of 3b (100 MHz, DMSO-d 6 ). S13
14 Figure S3. 1 H NMR of 3c (400 MHz, DMSO-d 6 ) and 13 C NMR of 3c (100 MHz, DMSOd 6 ). S14
15 Figure S4. 1 H NMR of 3d (400 MHz, DMSO-d 6 ) and 13 C NMR of 3d (100 MHz, DMSO-d 6 ). S15
16 Figure S5. 1 H NMR of 3e (400 MHz, DMSO-d 6 ) and 13 C NMR of 3e (100 MHz, DMSOd 6 ). S16
17 N N H Cl Cl N N H Cl Cl Figure S6. 1 H NMR of 3f (400 MHz, DMSO-d 6 ) and 13 C NMR of 3f (100 MHz, DMSOd 6 ). S17
18 Figure S7. 1 H NMR of 3g (400 MHz, DMSO-d 6 ) and 13 C NMR of 3g (100 MHz, DMSO-d 6 ). S18
19 Figure S8. 1 H NMR of 3h (400 MHz, DMSO-d 6 ) and 13 C NMR of 3h (100 MHz, DMSO-d 6 ). S19
20 Figure S9. 1 H NMR of 3i (400 MHz, DMSO-d 6 ) and 13 C NMR of 3i (100 MHz, DMSOd 6 ). S20
21 Figure S10. 1 H NMR of 3j (400 MHz, DMSO-d 6 ) and 13 C NMR of 3j (100 MHz, DMSO-d 6 ). S21
22 Figure S11. 1 H NMR of 3k (400 MHz, DMSO-d 6 ) and 13 C NMR of 3k (100 MHz, DMSO-d 6 ). S22
23 Figure S12. 1 H NMR of 3l (400 MHz, CDCl 3 ) and 13 C NMR of 3l (100 MHz, CDCl 3 ). S23
24 Figure S13. 1 H NMR of 3m (400 MHz, CDCl 3 ) and 13 C NMR of 3m (100 MHz, CDCl 3 ). S24
25 Figure S14. 1 H NMR of 3n (400 MHz, DMSO-d 6 ) and 13 C NMR of 3n (100 MHz, DMSO-d 6 ). S25
26 Figure S15. 1 H NMR of 3o (400 MHz, CDCl 3 ) and 13 C NMR of 3o (100 MHz, CDCl 3 ). S26
27 Figure S16. 1 H NMR of 3p (400 MHz, DMSO-d 6 ) and 13 C NMR of 3p (100 MHz, DMSO-d 6 ). S27
28 Figure S17. 1 H NMR of 3q (400 MHz, DMSO-d 6 ) and 13 C NMR of 3q (100 MHz, DMSO-d 6 ). S28
29 Figure S18. 1 H NMR of 5a (400 MHz, CDCl 3 ) and 13 C NMR of 5a (100 MHz, CDCl 3 ). S29
30 Me N O Me Me N O Me Figure S19. 1 H NMR of 5b (400 MHz, CDCl 3 ) and 13 C NMR of 5b (100 MHz, CDCl 3 ). S30
31 Figure S20. 1 H NMR of 5c (400 MHz, CDCl 3 ) and 13 C NMR of 5c (100 MHz, CDCl 3 ). S31
32 Figure S21. 1 H NMR of 5d (400 MHz, CDCl 3 ) and 13 C NMR of 5d (100 MHz, CDCl 3 ). S32
33 Figure S22. 1 H NMR of 5e (400 MHz CDCl 3 ) and 13 C NMR of 5e (100 MHz, CDCl 3 ). S33
34 Figure S23. 1 H NMR of 5f (400 MHz, CDCl 3 ) and 13 C NMR of 5f (100 MHz, CDCl 3 ). S34
35 Figure S24. 1 H NMR of 5g (400 MHz, CDCl 3 ) and 13 C NMR of 5g (100 MHz, CDCl 3 ). S35
36 Figure S25. 1 H NMR of 5h (400 MHz, CDCl 3 ) and 13 C NMR of 5h (100 MHz, CDCl 3 ). S36
37 Figure S26. 1 H NMR of 5i (400 MHz, CDCl 3 ) and 13 C NMR of 5i (100 MHz, CDCl 3 ). S37
38 Figure S27. 1 H NMR of 5j (400 MHz, CDCl 3 ) and 13 C NMR of 5j (100 MHz, CDCl 3 ). S38
39 Figure S28. 1 H NMR of 5k (400 MHz, CDCl 3 ) and 13 C NMR of 5k (100 MHz, CDCl 3 ). S39
40 Figure S29. 1 H NMR of 7a (400 MHz, CDCl 3 ) and 13 C NMR of 7a (100 MHz, CDCl 3 ). S40
41 Figure S30. 1 H NMR of 7b (400 MHz, CDCl 3 ) and 13 C NMR of 7b (100 MHz, CDCl 3 ). S41
42 Figure S31. 1 H NMR of 7c (400 MHz, CDCl 3 ) and 13 C NMR of 7c (100 MHz, CDCl 3 ). S42
43 Figure S32. 1 H NMR of 7d (400 MHz, CDCl 3 ) and 13 C NMR of 7d (100 MHz, CDCl 3 ). S43
44 Figure S33. 1 H NMR of 7e (400 MHz, CDCl 3 ) and 13 C NMR of 7e (100 MHz, CDCl 3 ). S44
45 N S Cl Cl Figure S34. 1 H NMR of 7f (400 MHz, CDCl 3 ) and 13 C NMR of 7f (100 MHz, CDCl 3 ). S45
46 Figure S35. 1 H NMR of 7g (400 MHz, CDCl 3 ) and 13 C NMR of 7g (100 MHz, CDCl 3 ). S46
47 N S O O N S O O Figure S36. 1 H NMR of 7h (400 MHz, CDCl 3 ) and 13 C NMR of 7h (100 MHz, CDCl 3 ). S47
48 Figure S37. 1 H NMR of 7i (400 MHz, CDCl 3 ) and 13 C NMR of 7i (100 MHz, CDCl 3 ). S48
49 Figure S38. 1 H NMR of 7j (400 MHz, CDCl 3 ) and 13 C NMR of 7j (100 MHz, CDCl 3 ). S49
50 Figure S39. 1 H NMR of 7k (400 MHz, CDCl 3 ) and 13 C NMR of 7k (100 MHz, CDCl 3 ). S50
51 Figure S40. 1 H NMR of 7l (400 MHz, CDCl 3 ) and 13 C NMR of 7l (100 MHz, CDCl 3 ). S51
52 Figure S41. 1 H NMR of 10 (400 MHz, CDCl 3 ) and 13 C NMR of 10 (100 MHz, CDCl 3 ). S52
53 N NH 2 N NH 2 Figure S42. 1 H NMR of 11 (400 MHz, CDCl 3 ) and 13 C NMR of 11 (100 MHz, CDCl 3 ). S53
54 HRMS Data N N H CF 3 CF 3 Figure S43. HRMS spectra for 2-(3,5-Bis(trifluoromethyl)phenyl)-1H-benzo[d]imidazole (3g). S54
55 Figure S44. HRMS spectra for 6-Nitro-2-(p-tolyl)-1H-benzo[d]imidazole (3n). S55
56 Figure S45. HRMS spectra for 2-(p-Tolyl)-1H-naphtho[2,3-d]imidazole (3p). S56
57 Figure S46. HRMS spectra for 2-(4-Fluorophenyl)-5-methylbenzo[d]oxazol (5d). S57
58 Me N O Cl Figure S47. HRMS spectra for 2-(2-Chlorophenyl)-5-methylbenzo[d]oxazole (5e). S58
59 Figure S48. HRMS spectra for 2-(3,4-Dichlorophenyl)-5-methyl-benzo[d]oxazole (5f). S59
60 Me N O CF 3 CF 3 Figure S49. HRMS spectra for 2-(3,5-Bis(trifluoromethyl)phenyl)-5- methylbenzo[d]oxazole (5g). S60
61 Me N O O O Figure S50. HRMS spectra for 2-(Benzo[d][1,3]dioxol-5-yl)-5-methylbenzo[d]oxazole (5h). S61
62 Me N O MeO Figure S51. HRMS spectra for 2-(2-Methoxyphenyl)-5-methylbenzo[d]oxazole (5i). S62
63 Me N O Figure S52. HRMS spectra for 5-Methyl-2-(naphthalen-1-yl)benzo[d]oxazole (5j). S63
64 Figure S53. HRMS spectra for 5-Methyl-2-(thiophen-2-yl)benzo[d]oxazole (5k). S64
65 Figure S54. HRMS spectra for 2-(3,4-Dichlorophenyl)benzo[d]thiazole (7f). S65
66 N S CF 3 CF 3 Figure S55. HRMS spectra for 2-(3,5-Bis(trifluoromethyl)phenyl)benzo[d]thiazole (7g). S66
67 N NH 2 Figure S56. HRMS spectra for N-benzylidenebenzene-1,2-diamine (11). S67
68 GC-MS Data Figure S57. GC-MS Spectra for Reaction of 1a with 2a (after 30 minutes). S68
69 Figure S58. GC-MS Spectra for Reaction of 1a with 2a (after 30 minutes). S69
70 Figure S59. GC-MS Spectra for Reaction of 1a with 2a (after 30 minutes). S70
71 Figure S60. GC-MS Spectra for Reaction of 1a with 2a (after 30 minutes). S71
72 Figure S61. GC-MS Spectra for Reaction of 1a with 2a (after 30 minutes). S72
73 Figure S62. GC-MS Spectra for Reaction of 1a with 2a (after 30 minutes). S73
74 Figure S63. GC-MS Spectra for Reaction of 1a with 2a (after 1 h). S74
75 Figure S64. GC-MS Spectra for Reaction of 1a with 2a (after 1.5 h). S75
76 Figure S65. GC-MS Spectra for Reaction of 1a with 2a (after 2 h). S76
77 Figure S66. GC-MS Spectra for Reaction of 1a with 2a (after 2.5 h). S77
78 Figure S67. GC-MS Spectra for Reaction of 1a with 2a (after 3 h). S78
79 Figure S68. GC-MS Spectra for Reaction of 1a with 2a (after 3.5 h). S79
80 References (1) Y. Kim, M. R. Kumar, N. Park, Y. Heo and S. Lee, J. Org. Chem., 2011, 76, (2) K. Bahrami, M. M. Khodaei and A. Nejati, Green Chem., 2010, 12, 1237 (3) G.-F. Chen, H.-D. Shen, H.-M. Jia, L.-Y. Zhang, H.-Y. Kang, Q.-Q. Qi, B.-H. Chen, J.-L. Cao and J.-T. Li, Aust. J. Chem., 2013, 66, 262. (4) G. Speier, J. Org. Chem., 1986, 51, 218. (5) R.-G. Xing, Y.-N. Li, Q. Liu, Q.-Y. Meng, J. Li, X.-X. Shen, Z. Liu, B. Zhou, X. Yao and Z.-L. Liu, Eur. J. Org. Chem., 2010, (6) T. B. Nguyen, L. Ermolenko, W. A. Dean and A. Al-Mourabit, Org. Lett., 2012, 14, (7) M. A. Chari, D. Shobha and T. Sasaki, Tetrahedron Lett., 2011, 52, 5575 (8) R. P. Kale, M. U. Shaikh, G. R. Jadhav and C. H. Gill, Tetrahedron Lett., 2009, 50, (9) W. Han, P. Mayer and A. R. Ofial, Chem. Eur. J., 2011, 17, (10) N. Park, Y. Heo, M. R. Kumar, Y. Kim, K. H. Song and S. Lee, Eur. J. Org. Chem., 2012, (11) H. Eshghi, M. Rahimizadeh, A. Shiri and P. Sedaghat, Bull. Korean Chem. Soc., 2012, 33, 515. S80
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