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Synthesis of 3-Substituted and 2,3-Disubstituted Quinazolinones via Cu-Catalyzed Aryl Amidation

Lanting Xu, Yongwen Jiang and Dawei Ma*

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: Madwmail.sioc.ac.cn

L. Xu, Y. Jiang, D. Ma, Org. Lett., 2012, 14, 1150-1153.

DOI: 10.1021/ol300084v


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Abstract

CuI/4-hydroxy-l-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide affords 3-substituted quinazolinones at 80°C. Other amides only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via a subsequent HMDS/ZnCl2 mediated condensative cyclization.

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Key Words

4(3H)-quinazolinones


ID: J54-Y2012-0480