Synthesis of 2, 4-diaminoquinazolines and tricyclic quinazolines by cascade reductive cyclization of methyl N-cyano-2-nitrobenzimidates

P Yin, N Liu, YX Deng, Y Chen, Y Deng…

Index: Yin, Ping; Liu, Nan; Deng, Yu-Xing; Chen, Yue; Deng, Yong; He, Ling Journal of Organic Chemistry, 2012 , vol. 77, # 6 p. 2649 - 2658

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Citation Number: 17

Abstract

An efficient route to N 4-substituted 2, 4-diaminoquinazolines has been developed by employing tandem condensation of cyanoimidate–amine and reductive cyclization in iron– HCl system. This method is tolerant of a following intramolecular N-alkylation and produces two fused heterocycles in a one-pot procedure. This protocol is a facile two-step synthesis of tricyclic quinazolines, which is effected by potent cyanoimidation and tandem reductive ...