Citation:
Gao Wentao, Fu Xinbo, Li Yang. Syntheses of Novel (E)-6-Chloro-2-arylvinylquinoline-3-formic Acid Derivatives[J]. Chemistry,
;2016, 79(7): 630-639,644.
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In this paper, (E)-6-chloro-2-arylvinylquinoline-3-formic acid derivatives 4a~f' were synthesized through a simple and efficient one-pot reaction from ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate (1) and aromatic aldehydes 3a~f'. The newly synthesized 32 compounds are firstly reported, and their structures had been characterized by IR, 1H NMR, 13C NMR and HR-MS.
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-
-
[1]
[1] Y L Chen, K C Fang, J Y Sheu et al. J. Med. Chem., 2001, 44(14):2374~2377.
-
[2]
[2] J P Michael. Nat. Prod. Rep., 2007, 24(1):223~246.
-
[3]
[3] Y L Chen, I L Chen, C M Lu et al. Bioorg. Med. Chem., 2004, 12(2):387~392.
-
[4]
[4] A Nayyar, A Malde, E Coutinho et al. Bioorg. Med. Chem., 2006, 14(21):7302~7310.
-
[5]
[5] A Baba, A Mori, T Yasuma. Chem. Pharm. Bull., 1999, 47(7):993~999.
-
[6]
[6] 杜鼎, 方建新. 有机化学, 2007, 27(11):1318~1336.
-
[7]
[7] K Mekouar, J F Mouscadet, D Desmaele et al. J. Med. Chem., 1998, 41(15):2846~2857.
-
[8]
[8] M Ouali, C Laboulais, H Leh et al. J. Med. Chem., 2000, 43(10):1949~1957.
-
[9]
[9] M Ouali, C Laboulais, H Leh et al. Acta Biochim. Pol., 2000, 47(1):11~22.
-
[10]
[10] M Normand-Bayle, C Benard, F Zouhiri et al. Bioorg. Med. Chem. Lett., 2005, 36(49):4019~4022.
-
[11]
[11] F Zouhiri, J F Mouscadet, K Mekouar. J. Med. Chem., 2000, 43(8):1533~1540.
-
[12]
[12] J Polanski, F Zouhiri, L Jeanson. J. Med. Chem., 2002, 45(21):4647~4654.
-
[13]
[13] N Neamati. Expert. Opin. Ther. Pat., 2005, 12(5):709~724.
-
[14]
[14] K Mekouar, J F Mouscadet, D Desmaele. J. Med. Chem., 1998, 41(15):2846~2857.
-
[15]
[15] F Zouhiri, D Desmaele, J Angelo et al. Tetrahed. Lett., 2001, 42(46):8189~8192.
-
[16]
[16] F S Chang, W C Chen, C H Wang et al. Bioorg. Med. Chem., 2010, 18(1):124~133.
-
[17]
[17] 刘鸿, 何丹丹. 应用化工, 2010, 39(3):380~383.
-
[18]
[18] 李凤梅, 王兰英, 王少康. 有机化学, 2004, 24(1):50~52.
-
[19]
[19] 李春兰, 王兰英, 孙国峰. 有机化学, 2006, 26(4):442~453.
-
[20]
[20] R Aspiotis, D Deschenes, D Dube et al. Bioorg. Med. Chem, Lett., 2010, 20(18):5502~5505.
-
[21]
[21] L H Wu, D Q Yang. Chin. J. Org. Chem., 2009, 29(7):1122~1128.
-
[22]
[22] Y Li, G H Lin, W T Gao. Polycycl. Aromat. Comp., 2012, 32(4):469~486.
-
[23]
[23] W T Gao, C H Zhang, Y Li. J. Braz. Chem. Soc., 2010, 21(5):806~812.
-
[24]
[24] 高文涛, 符鑫博, 李凯等. 化学研究与应用, 2015, 27(10):1463~1470.
-
[25]
[25] W T Gao, G H Lin, Y Li et al. Belistein. J. Org. Chem., 2012, 8:1849~1857.
-
[26]
[26] W T Gao, X D Xing, Y Li et al. Tetrahedron, 2014, 70(12):2180~2189.
-
[27]
[27] W T Gao, J Liu, Y Jiang et al. Belistein. J. Org. Chem., 2011, 7:210~217.
-
[28]
[28] 高文涛, 郑宏梅, 兰帅等. 化学研究与应用, 2015, 27(2):161~167.
-
[29]
[29] G W Stewart, K M Brands, S E Brewer et al. Org. Process. Res. Dev., 2010, 14(4):849~858.
-
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