Radical Cation Salts Induced aza-Diels-Alder Reaction: Synthesis of Hexahydrofuro[3,2-c]- quinoline Derivatives

Title: Radical Cation Salts Induced aza-Diels-Alder Reaction: Synthesis of Hexahydrofuro[3,2-c]- quinoline Derivatives

Volume: 9 Issue: 3

Author(s): Zhong Jia, Yan Ren, Cong-De Huo, Xiang-Ning Chen, Chong-Xiang Tong and Xiao-Dong Jia

Affiliation:

Keywords: Aza-Diels-Alder reaction, antiplatelet, analgesic, antipyretic, anti-inflammatory, antiallergic, furanoquinoline, tetrahydroquinoline, hexahydrofuro, quinoline, Hexahydrofuro[3,2-c]quinolines, radical cation

Abstract: Aza-Diels-Alder reaction between imines and 2,3-dihydrofuran under radical cation induced conditions was achieved and series of hexahydrofuro[3,2-c]quinoline derivatives was prepared. The stereoselectivity was affected by the substituents on imines, which revealed a stepwise mechanism. A radical cation mediated mechanism was proposed to rationalize the formation of the products.

Cite this article as:

Jia Zhong, Ren Yan, Huo Cong-De, Chen Xiang-Ning, Tong Chong-Xiang and Jia Xiao-Dong, Radical Cation Salts Induced aza-Diels-Alder Reaction: Synthesis of Hexahydrofuro[3,2-c]- quinoline Derivatives, Letters in Organic Chemistry 2012; 9 (3) . https://dx.doi.org/10.2174/157017812800167484