Synthesis of 2-Aminothiophene Derivatives Catalyzed by Amano Lipase M from Mucor javanicus
- Corresponding author: Jiang Guofang, zbxie@ecit.cn Le Zhanggao, zhgle@ecit.cn
Citation:
Lu Yue, Jiang Guofang, Xie Zongbo, Chen Guoqing, Le Zhanggao. Synthesis of 2-Aminothiophene Derivatives Catalyzed by Amano Lipase M from Mucor javanicus[J]. Chinese Journal of Organic Chemistry,
;2018, 38(7): 1837-1841.
doi:
10.6023/cjoc201801047
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.
doi: 10.1016/0960-894X(95)00450-8
Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 2, 333.
Hallas, G.; Towns, A. D. Dyes Pigm. 1996, 32, 135.
doi: 10.1016/0143-7208(96)00024-1
Dufresne, S.; Bourgeaux, M.; Skene, W. G. J. Mater. Chem. 2007, 17, 1166.
doi: 10.1039/B616379C
Huang, Y.; Dömling, A. Mol. Diversity 2011, 15, 3.
doi: 10.1007/s11030-010-9229-6
Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R. Beilstein J. Org. Chem. 2015, 11, 875.
doi: 10.3762/bjoc.11.98
Lütjens, H.; Zickgraf, A.; Figler, H.; Linden, J.; Olsson, R. A.; Scammells, P. J. J. Med. Chem. 2003, 46, 1870.
doi: 10.1021/jm020295m
(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.
(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.
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.
(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.
Mojtahedi, M. M.; Abaee, M. S.; Mahmoodi, P.; Adib, M. Synth. Commun. 2010, 40, 2067.
doi: 10.1080/00397910903219435
(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.
Wallace, S.; Balskus, E. P. Curr. Opin. Biotechnol. 2014, 30, 1.
Reyes, A. C.; Zhai, X.; Morgan, K. T.; Reinhardt, C. J.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 2015, 137, 1372.
doi: 10.1021/ja5123842
Ge, X.; Lai, Y.-F.; Chen, X.-Z. Chin. J. Org. Chem. 2013, 33, 1686 (in Chinese).
Zhang, C.; Zhang, L. J.; Zhang, Y.; Huang, H.; Hu, Y. Acta Chim. Sinica 2016, 74, 74 (in Chinese).
Li, K..; He, T.; Li, C.; Feng, X. W.; Wang, N.; Yu, X. Q. Green Chem. 2009, 11, 777.
doi: 10.1039/b817524a
Ding, Y.; Huang, H.; Hu, Y. Chin. J. Org. Chem. 2013, 33, 905 (in Chinese).
Ding, Y.; Ni, X.; Gu, M.; Li, S.; Huang, H.; Hu, Y. Catal. Commun. 2015, 65, 101.
Cai, Y.; Sun, X. F.; Wang, N.; Lin, X. F. Synthesis 2004, 671.
Acharya, C.; Achari, A.; Jaisankar, P. Tetrahedron Lett. 2018, 59, 663.
doi: 10.1016/j.tetlet.2018.01.009
Liang, M.; Xie, Z. B.; Ai, F.; Le, Z. G. Chin. J. Org. Chem. 2016, 36, 2704 (in Chinese).
Ma, L.; Yuan, L.; Xu, C.; Li, G.; Tao, M.; Zhang, W. Synthesis 2013, 45.
Polívka, Z.; Holubek, J.; Svátek, E.; Metyš, J.; Protiva, M. Collect. Czech. Chem. Commun. 1984, 49, 621.
doi: 10.1135/cccc19840621
Li, P.; Du, J.; Xie, Y.; Tao, M.; Zhang, W. Q. ACS Sustainable Chem. Eng. 2016, 4, 1139.
doi: 10.1021/acssuschemeng.5b01216
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