Palladium-catalyzed oxidative CC bond cleavage with molecular oxygen: one-pot synthesis of quinazolinones from 2-amino benzamides and alkenes

Wei Liu; Ge Wu; Wenxia Gao; Jinchang Ding; Xiaobo Huang; Miaochang Liu; Huayue Wu

doi:10.1039/C8QO00670A

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Palladium-catalyzed oxidative CC bond cleavage with molecular oxygen: one-pot synthesis of quinazolinones from 2-amino benzamides and alkenes†

Wei Liu,^a Ge Wu,

*^b Wenxia Gao,

^a Jinchang Ding,^a Xiaobo Huang,

^a Miaochang Liu

*^a and Huayue Wu

Author affiliations

* Corresponding authors

^a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China
E-mail: mcl@wzu.edu.cn

^b School of Pharmaceutical Science, Wenzhou Medical University, Wenzhou 325035, People's Republic of China
E-mail: wuge@wmu.edu.cn

Abstract

Palladium-catalyzed oxidative cleavage/cyclization has been disclosed for the concise synthesis of various quinazolinone derivatives from readily available 2-aminobenzamides and terminal alkenes with excellent functional group tolerance. The synthetic features regarding the use of oxygen as a green oxidant and its utility are illustrated in the synthesis of sildenafil.

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Article information

DOI: https://doi.org/10.1039/C8QO00670A
Article type: Research Article
Submitted: 05 Jul 2018
Accepted: 16 Aug 2018
First published: 17 Aug 2018

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Org. Chem. Front., 2018,5, 2734-2738

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Palladium-catalyzed oxidative CC bond cleavage with molecular oxygen: one-pot synthesis of quinazolinones from 2-amino benzamides and alkenes

W. Liu, G. Wu, W. Gao, J. Ding, X. Huang, M. Liu and H. Wu, Org. Chem. Front., 2018, 5, 2734 DOI: 10.1039/C8QO00670A

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Organic Chemistry Frontiers

Palladium-catalyzed oxidative CC bond cleavage with molecular oxygen: one-pot synthesis of quinazolinones from 2-amino benzamides and alkenes†

Abstract

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Palladium-catalyzed oxidative CC bond cleavage with molecular oxygen: one-pot synthesis of quinazolinones from 2-amino benzamides and alkenes

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