Highly efficient access to 4-chloro-2H-chromenes and 1, 2-dihydroquinolines under mild conditions: TMSCl-mediated cyclization of 2-propynolphenols/anilines. Issue 41 (12th October 2016)

• Record Type: Journal Article
• Authors: Song, Xian-Rong; Li, Ren; Ding, Haixin; Yang, Ruchun; Xiao, Qiang; Liang, Yong-Min
• Is Part Of: Tetrahedron letters. Volume 57:Issue 41(2016)
• Page Start: 4519
• Page End: 4524
• Publication Date: 2016-10-12
• Subjects: 2-Propynolphenols/anilines -- 4-Chloro-2H-chromenes/quinolines -- TMSCl-mediated -- Cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.07.103
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: TMSCl-mediated synthesis of 4-chloro-2 H -chromenes and 1, 2-dihydroquinolines. Both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated. TMSCl acts not only as a promoter in this reaction, and also as the chloro source. This method can be enlarged to gram scale (yield up to 90%). Abstract: A novel and efficient TMSCl-mediated cyclization reaction of easily prepared 2-propynolphenols/anilines is developed to give 4-chloro-2 H -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%).