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Synthesis 2013; 45(24): 3349-3354
DOI: 10.1055/s-0033-1340040
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Domino Synthesis of Quinazolin-4(3H)-ones from (Hetero)arylmethyl Halides, Bromoacetate, and Cinnamyl Bromide

Haidong Wei
a   Institute of Green Catalysis and Synthesis, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, P. R. of China   Fax: +86(28)84079074   Email: qinglezeng@hotmail.com
,
Tianbin Li
b   State Key Lab of Geohazard Prevention and Geoenvironment Protection, Chengdu University of Technology, Chengdu 610059, P. R. of China
,
Yue Zhou
a   Institute of Green Catalysis and Synthesis, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, P. R. of China   Fax: +86(28)84079074   Email: qinglezeng@hotmail.com
,
Lihong Zhou
a   Institute of Green Catalysis and Synthesis, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, P. R. of China   Fax: +86(28)84079074   Email: qinglezeng@hotmail.com
,
Qingle Zeng*
a   Institute of Green Catalysis and Synthesis, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, P. R. of China   Fax: +86(28)84079074   Email: qinglezeng@hotmail.com
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Further Information

Publication History

Received: 21 August 2013

Accepted after revision: 23 September 2013

Publication Date:
18 October 2013 (online)

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Abstract

Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed.

Key words

copper - condensation - tandem reaction - oxygenation - quinazolin-4(3H)-ones

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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