Issue 17, 2021

Access to diverse primary, secondary, and tertiary amines via the merger of controllable cleavage of triazines and site-selective functionalization

Abstract

An efficient approach for divergent synthesis of primary, secondary, and tertiary amines via the merger of controllable cleavage of triazines and site-selective functionalization is disclosed. This transformation proceeded with imidazo [1,2-a]pyridines and readily available triazines by Lewis acid catalysis and Hofmann–Martius type rearrangement. A number of imidazo [1,2-a]pyridines-containing primary and secondary aromatic amines, and trialkylamines were facilely accessed with a wide range of functional groups. Importantly, the obtained aromatic amines could be incorporated with important bioactive units and converted into many valuable nitrogen-containing molecules. In addition, the results revealed that Hofmann–Martius type rearrangement exhibits excellent o- and p-selectivity and goes through an intermolecular process.

Graphical abstract: Access to diverse primary, secondary, and tertiary amines via the merger of controllable cleavage of triazines and site-selective functionalization

Supplementary files

Article information

Article type
Research Article
Submitted
13 Jūn. 2021
Accepted
28 Jūn. 2021
First published
29 Jūn. 2021

Org. Chem. Front., 2021,8, 4706-4714

Access to diverse primary, secondary, and tertiary amines via the merger of controllable cleavage of triazines and site-selective functionalization

Y. Wang, H. Zheng, J. Xu, C. Zhuang, X. Liu and H. Cao, Org. Chem. Front., 2021, 8, 4706 DOI: 10.1039/D1QO00883H

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