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AlCl3-Catalyzed Intramolecular Cyclization of N-Arylpropynamides with N-Sulfanylsuccinimides: Divergent Synthesis of 3-Sulfenyl Quinolin-2-ones and Azaspiro[4,5]trienones

Author:
Gao, Wen-Chao, Liu, Tao, Cheng, Yu-Fei, Chang, Hong-Hong, Li, Xing, Zhou, Rong, Wei, Wen-Long, Qiao, Yan
Source:
Journal of organic chemistry 2017 v.82 no.24 pp. 13459-13467
ISSN:
1520-6904
Subject:
chemical structure, cyclization reactions, methanol, organic chemistry, quinoline, quinolones, sulfur
Abstract:
Switchable ortho/ipso-cyclization of N-arylpropynamides induced with N-sulfanylsuccinimides as general sulfur reagents is reported. In the presence of MeOH, para-fluoro N-arylpropynamides exclusively undergo the ipso-cyclization to give 3-sulfenyl azaspiro[4,5]trienones. Two kinds of bioactive heterocycles, benzothieno-[3,2-b]quinoline and -[2,3-c]quinolone, have been directly and efficiently prepared from the corresponding sulfenylated products.
Agid:
5871309