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

Organic Chemistry Frontiers Pub Date: 2021-06-29 DOI: 10.1039/D1QO00883H

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
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