Issue 3, 2021
From the journal:

Organic Chemistry Frontiers

Cascade C–N bond cleavage of amides/intramolecular amination reactions: an atom economical way to α-cabolin-4-ones†

Ye Wang,‡a   Zhong Zheng, ORCID logo ‡a   Yang Yuan, ORCID logo a   Mengdan Wang,a   Zixia Guo,a   Yuan-Ye Jiang, ORCID logo *b   Li-Ping Bai ORCID logo *c  and  Yanzhong Li ORCID logo *a  

* Corresponding authors

a School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai, China
E-mail: yzli@chem.ecnu.edu.cn

b School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, China
E-mail: yuanyejiang@qfnu.edu.cn

c State Key Laboratory of Quality Research in Chinese Medicine, and Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Taipa, Macau
E-mail: lpbai@must.edu.mo

Abstract

An atom economical approach for the synthesis of α-carbolin-4-ones has been developed. This process was realized via a C–N bond cleavage/intramolecular amination cascade. During this process, one C–N and one C–C bond are cleaved and two C–N and two C–C bonds are formed. Mechanistic studies suggested a migrative N-cyclization process involving a carbene intermediate.

Graphical abstract: Cascade C–N bond cleavage of amides/intramolecular amination reactions: an atom economical way to α-cabolin-4-ones

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Article information

DOI
https://doi.org/10.1039/D0QO01257B
Article type
Research Article
Submitted
12 Oct 2020
Accepted
24 Nov 2020
First published
28 Nov 2020

Org. Chem. Front., 2021,8, 579-583

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Cascade C–N bond cleavage of amides/intramolecular amination reactions: an atom economical way to α-cabolin-4-ones

Y. Wang, Z. Zheng, Y. Yuan, M. Wang, Z. Guo, Y. Jiang, L. Bai and Y. Li, Org. Chem. Front., 2021, 8, 579 DOI: 10.1039/D0QO01257B

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