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
03 ذو القعدة 1442
Accepted
18 ذو القعدة 1442
First published
19 ذو القعدة 1442

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

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