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Issue 103, 2014
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Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: application to the synthesis of the alkaloid tryptanthrin

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Abstract

An efficient and practical procedure for the preparation of 2-substituted and 2,3-disubstituted quinazolinones was achieved through copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia under air. Control experimental results indicated that this tandem reaction is triggered by a copper-catalyzed direct amination of 2-bromobenzamides with aqueous ammonia, followed by cyclocondensation and oxidative aromatization. As an application, this novel methodology provides a concise and practical one-pot route to the synthesis of alkaloid tryptanthrin.

Graphical abstract: Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: application to the synthesis of the alkaloid tryptanthrin

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Publication details

The article was received on 19 Sep 2014, accepted on 31 Oct 2014 and first published on 03 Nov 2014


Article type: Paper
DOI: 10.1039/C4RA10799C
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Citation: RSC Adv., 2014,4, 59289-59296
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    Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: application to the synthesis of the alkaloid tryptanthrin

    S. Guo, Y. Li, L. Tao, W. Zhang and X. Fan, RSC Adv., 2014, 4, 59289
    DOI: 10.1039/C4RA10799C

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