Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4

Xu Liu; Xin Xin; Dexuan Xiang; Rui Zhang; Santosh Kumar; Fenguo Zhou; Dewen Dong

doi:10.1039/C2OB25767J

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Facile and efficient synthesis of quinolin-2(1H)-ones viacyclization of penta-2,4-dienamides mediated by H₂SO₄†

Xu Liu,^a Xin Xin,^a Dexuan Xiang,^a Rui Zhang,*^a Santosh Kumar,^a Fenguo Zhou^a and Dewen Dong*^a

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* Corresponding authors

^a Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, China
E-mail: dwdong@ciac.jl.cn, ariel@ciac.jl.cn

Abstract

A facile and efficient synthesis of substituted quinolin-2(1H)-ones is developed via intramolecular cyclization of penta-2,4-dienamides mediated by concentrated H₂SO₄ (98%), and a mechanism involving the formation of a dicationic superelectrophile, and subsequent intramolecular nucleophilic cyclization reactions is proposed.

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Article information

DOI: https://doi.org/10.1039/C2OB25767J
Article type: Paper
Submitted: 21 Apr 2012
Accepted: 01 Jun 2012
First published: 01 Jun 2012

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Org. Biomol. Chem., 2012,10, 5643-5646

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Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H₂SO₄

X. Liu, X. Xin, D. Xiang, R. Zhang, S. Kumar, F. Zhou and D. Dong, Org. Biomol. Chem., 2012, 10, 5643 DOI: 10.1039/C2OB25767J

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Organic & Biomolecular Chemistry