Synlett 2013; 24(16): 2089-2094
DOI: 10.1055/s-0033-1339800
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Sequential N-Arylation and Aerobic Oxidation: Synthesis of Quinazoline Derivatives

Qing Liu
a   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Fax: +86(10)62781695   eMail: fuhua@mail.tsinghua.edu.cn
,
Yufen Zhao
a   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Fax: +86(10)62781695   eMail: fuhua@mail.tsinghua.edu.cn
,
Hua Fu*
a   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Fax: +86(10)62781695   eMail: fuhua@mail.tsinghua.edu.cn
b   Key Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. of China
,
Changmei Cheng*
a   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Fax: +86(10)62781695   eMail: fuhua@mail.tsinghua.edu.cn
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Publikationsverlauf

Received: 15. Juli 2013

Accepted after revision: 06. August 2013

Publikationsdatum:
27. August 2013 (online)


Abstract

A novel and efficient copper-catalyzed cascade method for the synthesis of quinazoline derivatives has been developed. The protocol uses readily available substituted (2-bromophenyl)methylamines and amidine hydrochlorides as the starting materials, inexpensive CuBr as the catalyst, and economical and environment friendly air as the oxidant, and the corresponding quinazoline derivatives were obtained in moderate to good yields. The procedure underwent sequential intermolecular N-arylation, intramolecular nucleophilic substitution and aerobic oxidation.

Supporting Information

 
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