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Issue 12, 2017
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A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes

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Abstract

A facile and general Brønsted acid-catalyzed deuteration at the methyl group of N-heteroarylmethanes was achieved through a dearomatic enamine intermediate under relatively mild reaction conditions. Both 2-methyl and 4-methyl groups in quinolines were deuterated with high deuterium incorporation. Pyridines, benzo[d]thiazoles, indoles and imines including these clinical drugs were also deuterated efficiently at the methyl groups. This reaction could be conducted on a large scale (500 mmol), showing its good potential for use in large-scale synthesis.

Graphical abstract: A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes

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Supplementary files

Article information


Submitted
10 Jan 2017
Accepted
28 Feb 2017
First published
28 Feb 2017

Org. Biomol. Chem., 2017,15, 2507-2511
Article type
Communication

A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes

M. Liu, X. Chen, T. Chen and S. Yin, Org. Biomol. Chem., 2017, 15, 2507
DOI: 10.1039/C7OB00062F

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