Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones

Junhui He, Jianyu Dong, Lebin Su, Shaofeng Wu, Lixin Liu, Shuang-Feng Yin and Yongbo Zhou*

*State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China, Email: zhouybhnu.edu.cn

J. He, J. Dong, L. Su, S. Wu, L. Liu, S.-F. Yin, Y. Zhou, Org. Lett., 2020, 22, 2522-2526.

DOI: 10.1021/acs.orglett.0c00271

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Abstract

An n-Bu₄NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant provides broad range of quinazolinones in very good yields. The reaction involves oxygenation, nitrogenation, ring-opening, and recyclization.

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proposed mechanism

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Key Words

quinazolinones, tert-butyl hydroperoxide, indoles

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ID: J54-Y2020