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Synthesis of 2,4-Diaminoquinazolines and Tricyclic Quinazolines by Cascade Reductive Cyclization of Methyl N-Cyano-2-nitrobenzimidates

Ping Yin, Nan Liu, Yu-Xing Deng, Yue Chen, Yong Deng* and Ling He*

*Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. China, Email: lhe2001sina.com, dengyongysohu.com

P. Yin, N. Liu, Y.-X. Deng, Y. Chen, Y. Deng, L. He, J. Org. Chem., 2012, 77, 2649-2658.

DOI: 10.1021/jo2023697 (free Supporting Information)


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Abstract

A tandem condensation of a cyanoimidate with an amine followed by reductive cyclization in an iron-HCl system enables an efficient route to N4-substituted 2,4-diaminoquinazolines. An additional N-alkylation can produce two fused heterocycles in a one-pot procedure.

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Key Words

Quinazolines, Iron


ID: J42-Y2012-0680