爪哇毛霉脂肪酶催化合成2-氨基噻吩衍生物
收稿日期: 2018-01-30
修回日期: 2018-03-17
网络出版日期: 2018-04-04
基金资助
国家自然科学基金（Nos.21462001，21262002，21465002）、江西省科技计划（No.20161BCB24006）、江西省教育厅科技（Nos.KJLD14050，GJJ150584）资助项目.
Synthesis of 2-Aminothiophene Derivatives Catalyzed by Amano Lipase M from Mucor javanicus
Received date: 2018-01-30
Revised date: 2018-03-17
Online published: 2018-04-04
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21462001, 21262002, 21465002), the Science and Technology Projects of Jiangxi Province (No. 20161BCB24006), the Science and Technology Foundation of the Jiangxi Provincial Education Department (Nos. KJLD14050, GJJ150584).
以α-活性亚甲基腈和2，5-二羟基-1，4-二噻烷为原料，通过爪哇毛霉脂肪酶催化的Gewald反应合成了一系列2-氨基噻吩类化合物.该方法与传统的化学催化方法相比，具有反应条件温和、催化剂可生物降解、底物适用范围较宽泛等优点.
关键词： α-活性亚甲基腈; 2,5-二羟基-1,4-二噻烷; 脂肪酶; Gewald反应; 2-氨基噻吩
卢粤 , 姜国芳 , 谢宗波 , 陈国庆 , 乐长高 . 爪哇毛霉脂肪酶催化合成2-氨基噻吩衍生物[J]. 有机化学, 2018 , 38(7) : 1837 -1841 . DOI: 10.6023/cjoc201801047
A series of 2-aminothiophene derivatives were synthesized by the Gewald reaction between α-active methylene nitrilthes and 2,5-dihydroxy-1,4-dithiane using amano lipase M from Mucor javanicus as biocatalyst. The method has the advantages of mild reaction conditions, biodegradability of catalyst and wide range of substrates compared with traditional catalysts.
[1] Blackburn, T. P.; Davies, D. T.; Forbes, I. T.; Hayward, C. J.; Johnson, C. N.; Martin, R. T.; Piper, D. C.; Thomas, D. R.; Thompson, M.; Upton, N.; Ward, R. W. Bioorg. Med. Chem. Lett. 1995, 5, 2589.
[2] Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 2, 333.
[3] Hallas, G.; Towns, A. D. Dyes Pigm. 1996, 32, 135.
[4] Dufresne, S.; Bourgeaux, M.; Skene, W. G. J. Mater. Chem. 2007, 17, 1166.
[5] Huang, Y.; Dömling, A. Mol. Diversity 2011, 15, 3.
[6] Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R. Beilstein J. Org. Chem. 2015, 11, 875.
[7] Lütjens, H.; Zickgraf, A.; Figler, H.; Linden, J.; Olsson, R. A.; Scammells, P. J. J. Med. Chem. 2003, 46, 1870.
[8] (a) Barnes, D. M.; Haight, A. R.; Hameury, T.; McLaughlin, M. A.; Mei, J.; Tedrow, J. S.; Toma, J. D. R. Tetrahedron 2006, 62, 11311.
(b) Moeinpour, F.; Omidinia, R.; Dorostkar-Ahmadi, N.; Khoshdeli, B. Bull. Korean Chem. Soc. 2011, 32, 2091.
[9] (a) Hu, Y.; Chen, Z. C.; Le, Z. G.; Zheng, Q. G. Synth. Commun. 2004, 34, 3801.
(b) Hu, Y.; Wei, P.; Huang, H.; Han, S. Q.; Ouyang, P. K. Heterocycles 2006, 68, 375.
[10] Wang, T.; Huang, X. G.; Liu, J.; Li, B.; Wu, J. J.; Chen, K. X.; Zhu, W. L.; Xu, X. Y.; Zeng, B. B. Synlett 2010, 1351.
[11] (a) Sridhar, M.; Rao, R. M.; Baba, N. H. K.; Kumbhare, R. M. Tetrahedron Lett. 2007, 48, 3171.
(b) Hesse, S.; Perspicace, E.; Kirsch, G. Tetrahedron Lett. 2007, 48, 5261.
(c) Hoener, A. P. F.; Henkel, B.; Gauvina, J. C. Synlett 2003, 63.
[12] Mojtahedi, M. M.; Abaee, M. S.; Mahmoodi, P.; Adib, M. Synth. Commun. 2010, 40, 2067.
[13] (a) Drauz, K. Enzyme Catalysis in Organic Synthesis:A Comprehensive Handbook, John Wiley & Sons, Weinheim, 2012, pp. 67~69.
(b) Du, L. L.; Wu, Q.; Chen, C. X.; Liu, B. K.; Lin, X. F. J. Mol. Catal. B:Enzym. 2009, 58, 208.
[14] Wallace, S.; Balskus, E. P. Curr. Opin. Biotechnol. 2014, 30, 1.
[15] (a) Zhang, S. G.; Xie, Z. B.; Liu, L. S.; Liang, M.; Le, Z. G. Chin. Chem. Lett. 2017, 1, 020.
(b) Xie, Z. B.; Zhang, S. G.; Jiang, G. F.; Liang, M.; Le, Z. G. Chin. J. Org. Chem. 2016, 37, 514 (in Chinese).
(谢宗波, 张士国, 姜国芳, 梁萌, 乐长高, 有机化学, 2016, 37, 514.)
(c) Mo, T.; Wang, J.; Gao, B. W.; Zhang, L.; Liu, X.; Wang, X. H.; Tu, P. F.; Shi, S. P. Chin. J. Org. Chem. 2015, 35, 1052 (in Chinese).
(莫婷, 王娟, 高博闻, 张乐, 刘晓, 王晓辉, 涂鹏飞, 史社坡, 有机化学, 2015, 35, 1052.)
[16] Reyes, A. C.; Zhai, X.; Morgan, K. T.; Reinhardt, C. J.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 2015, 137, 1372.
[17] Ge, X.; Lai, Y.-F.; Chen, X.-Z. Chin. J. Org. Chem. 2013, 33, 1686 (in Chinese).
(葛新, 赖依峰, 陈新志, 有机化学, 2013, 33, 1686.)
[18] Zhang, C.; Zhang, L. J.; Zhang, Y.; Huang, H.; Hu, Y. Acta Chim. Sinica 2016, 74, 74 (in Chinese).
(张川, 张鲁嘉, 张洋, 黄和, 胡燚, 化学学报, 2016, 74, 74.)
[19] Li, K..; He, T.; Li, C.; Feng, X. W.; Wang, N.; Yu, X. Q. Green Chem. 2009, 11, 777.
[20] Ding, Y.; Huang, H.; Hu, Y. Chin. J. Org. Chem. 2013, 33, 905 (in Chinese).
(丁雁, 黄和, 胡燚, 有机化学, 2013, 33, 905.)
[21] Ding, Y.; Ni, X.; Gu, M.; Li, S.; Huang, H.; Hu, Y. Catal. Commun. 2015, 65, 101.
[22] Cai, Y.; Sun, X. F.; Wang, N.; Lin, X. F. Synthesis 2004, 671.
[23] Acharya, C.; Achari, A.; Jaisankar, P. Tetrahedron Lett. 2018, 59, 663.
[24] Liang, M.; Xie, Z. B.; Ai, F.; Le, Z. G. Chin. J. Org. Chem. 2016, 36, 2704 (in Chinese).
(梁萌, 谢宗波, 艾锋, 乐长高, 有机化学, 2016, 36, 2704.)
[25] Ma, L.; Yuan, L.; Xu, C.; Li, G.; Tao, M.; Zhang, W. Synthesis 2013, 45.
[26] Polívka, Z.; Holubek, J.; Svátek, E.; Metyš, J.; Protiva, M. Collect. Czech. Chem. Commun. 1984, 49, 621.
[27] Li, P.; Du, J.; Xie, Y.; Tao, M.; Zhang, W. Q. ACS Sustainable Chem. Eng. 2016, 4, 1139.
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