A three-component one-pot synthesis of 2-alkoxy-4-amino-N-arylthiazole-5-carboxamides
English
A three-component one-pot synthesis of 2-alkoxy-4-amino-N-arylthiazole-5-carboxamides
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Key words:
- 4-Aminothiazole-5-carboxamide
- / Potassium methyl
- / cyanimidodithiocarbonate
- / Acetamide
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[21] The synthetic procedure and structure identification for compounds 2a-j, 4a-i and 4k-r are available in Supporting information. All synthesized final products were characterized by 1H NMR, 13C NMR and ESI-HRMS. For example, compound 4a: light yellow solid; mp 179-182 ℃; 1H NMR (300 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.27 (s, 1H), 7.79-7.89 (m, 3H), 7.58 (dd, 1H, J1 = 8.7 Hz, J2 = 2.1 Hz), 7.48 (t, 1H, J = 6.9 Hz), 7.38 (t, 1H, J = 7.2 Hz), 6.95 (brs, 2H), 4.14 (q, 2H, J = 6.9 Hz), 1.22 (t, 3H, J = 6.9 Hz); 13C NMR (100 MHz, DMSO-d6): δ 165.04, 163.47, 137.56, 133.60, 129.41, 128.73, 127.53, 127.02, 126.61, 124.44, 119.59, 113.80, 58.97, 14.65; HRMS (ESI) Calcd. for C16H16N3O2S [M+H+]: 314.0958; found: 314.0957.[21] The synthetic procedure and structure identification for compounds 2a-j, 4a-i and 4k-r are available in Supporting information. All synthesized final products were characterized by 1H NMR, 13C NMR and ESI-HRMS. For example, compound 4a: light yellow solid; mp 179-182 ℃; 1H NMR (300 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.27 (s, 1H), 7.79-7.89 (m, 3H), 7.58 (dd, 1H, J1 = 8.7 Hz, J2 = 2.1 Hz), 7.48 (t, 1H, J = 6.9 Hz), 7.38 (t, 1H, J = 7.2 Hz), 6.95 (brs, 2H), 4.14 (q, 2H, J = 6.9 Hz), 1.22 (t, 3H, J = 6.9 Hz); 13C NMR (100 MHz, DMSO-d6): δ 165.04, 163.47, 137.56, 133.60, 129.41, 128.73, 127.53, 127.02, 126.61, 124.44, 119.59, 113.80, 58.97, 14.65; HRMS (ESI) Calcd. for C16H16N3O2S [M+H+]: 314.0958; found: 314.0957.
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