α-羰基二硫缩烯酮的吲哚化反应

摘要

研究了BINOL酸催化α-羰基二硫缩烯酮的吲哚化反应,合成了12个β-吲哚基-β-乙硫基缩烯酮类化合物(3a~3l),其中3a, 3d~3e, 3g~3k为新化合物,其结构经1H NMR, 13C NMR, IR和HR-MS表征.对反应条件进行了优化.结果表明:20 mol%BINOL酸为催化剂,3,3-二乙硫基苯丙烯酮与吲哚于85 ℃反应2.5 h, 3-吲哚基-3-乙硫基苯丙烯酮收率85%.%The binaphthol acid controlled indolylation reaction of α-oxo ketene dithioacetals was studied.Twelve β-indolyl-β-ethylthio acetal compounds(3a~3l) were synthesized, among them 3a, 3d~3e, 3g~3k were novel compounds.The structures were characterized by 1H NMR, 13C NMR, IR and HR-MS.The reaction conditions were optimized.The results showed that the alkylation of 3,3-bis(ethylthio) acrylophenone with indole in the presence of BINOL acid(20 mol%) at 85 ℃ for 2.5 h, affording 3-(3-indolyl)-3-(ethylthio) acrylophenone in the yield of 85%.