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Highly efficient access to 4-chloro-2H-chromenes and 1,2-dihydroquinolines under mild conditions: TMSCl-mediated cyclization of 2-propynolphenols/anilines
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2016-08-01 , DOI: 10.1016/j.tetlet.2016.07.103
Xian-Rong Song , Ren Li , Haixin Ding , Ruchun Yang , Qiang Xiao , Yong-Min Liang

A novel and efficient TMSCl-mediated cyclization reaction of easily prepared 2-propynolphenols/anilines is developed to give 4-chloro-2H-chromenes and 1,2-dihydroquinolines in good to efficient yields. It is noted that TMSCl acts not only as a promoter in this reaction, and also as the chloro source. Both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under mild conditions. Moreover, this method can be enlarged to gram scale (yield up to 90%).



中文翻译:

在温和条件下高效地获得4-氯-2 H-二甲基苯醌和1,2-二氢喹啉:TMSCl介导的2-丙炔酚/苯胺环化

开发了易于制备的2-丙炔酚/苯胺的新颖且有效的TMSC1介导的环化反应,以良好至有效的产率获得了4-氯-2 H-色烯和1,2-二氢喹啉。注意到,TMCSC1不仅在该反应中充当促进剂,而且还充当氯源。具有温和条件的具有不同官能团的叔炔丙醇和仲炔丙醇都可以耐受。而且,该方法可以扩大到克级(产率高达90%)。

更新日期:2016-08-01
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