A three-component one-pot synthesis of 2-alkoxy-4-amino-N-arylthiazole-5-carboxamides

Hai-Long Zhao Jie Zhou Hong-Rui Song Bai-Ling Xu

Citation:  Hai-Long Zhao, Jie Zhou, Hong-Rui Song, Bai-Ling Xu. A three-component one-pot synthesis of 2-alkoxy-4-amino-N-arylthiazole-5-carboxamides[J]. Chinese Chemical Letters, 2014, 25(3): 411-414. doi: 10.1016/j.cclet.2013.12.005 shu

A three-component one-pot synthesis of 2-alkoxy-4-amino-N-arylthiazole-5-carboxamides

    通讯作者: Bai-Ling Xu,
  • 基金项目:

    This work is supported by the National Natural Science Foundation of China (No. 81273380)  (No. 81273380)

    "863" Program of China (No. 2012AA020302). (No. 2012AA020302)

摘要: A facile and efficient protocol was developed to access 2-alkoxy-4-amino-N-arylthiazole-5-carboxamides through a three-component one-pot reaction, which involved potassium methyl cyanimidodithiocarbonate, 2-halo-N-arylacetamides and alcohols. The easy availability and the broad structural diversity of substrates make the reaction useful for the construction of libraries in drug discovery.

English

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    21. [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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  • 发布日期:  2013-12-08
  • 收稿日期:  2013-09-04
  • 网络出版日期:  2013-11-25
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