Issue 3, 2023

Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives

Abstract

An efficient synthesis of multi-substituted pyridines and pyrroles from aryl methyl ketones with 1-amino-2-methylpropan-2-ol and 1,2-diamino-2-methylpropane, respectively, has been developed. The reactions each involved cleavage of one C–N bond and formation of two new bonds, namely a C–C bond and C–N bond, during an oxidative cyclization process promoted by I2/PhNO2. The C–N bond adjacent to the primary carbon of 1,2-diamino-2-methylpropane was the one selectively cleaved.

Graphical abstract: Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
09 Nov 2022
Accepted
06 Dec 2022
First published
09 Dec 2022

Org. Chem. Front., 2023,10, 780-785

Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives

R. Zhang, Y. Ding, R. Ma, X. Xiao, R. Chen, L. Wang and Y. Ma, Org. Chem. Front., 2023, 10, 780 DOI: 10.1039/D2QO01789J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements