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Expeditious Synthesis of 2-Phenylquinazolin-4-amines via a Fe/Cu Relay-Catalyzed Domino Strategy

Feng-Cheng Jia, Zhi-Wen Zhou, Cheng Xu, Qun Cai, Deng-Kui Li and An-Xin Wu*

*Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Hubei, Wuhan 430079, P. R. China, Email: chwuaxmail.ccnu.edu.cn

F.-C. Jia, Z.-W. Zhou, C. Xu, Q. Cai, D.-K. Li, A.-X. Wu, Org. Lett., 2015, 17, 4236-4239.

DOI: 10.1021/acs.orglett.5b02020 (free Supporting Information)


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Abstract

A highly efficient Fe/Cu relay-catalyzed domino protocol for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide involves consecutive iron-mediated [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, oxidation, and copper-catalyzed denitrogenation sequences. The formed structure is the privileged core in drugs and bioactive molecules.


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Key Words

quinazolines, multicomponent reactions


ID: J54-Y2015