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Issue 67, 2016
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Formation of amides, their intramolecular reactions for the synthesis of N-heterocycles, and preparation of a marketed drug, sildenafil: a comprehensive coverage

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Abstract

A unified approach to the tandem preparation of diverse nitrogen heterocycles via decarboxylative acylation of ortho-substituted amines with α-oxocarboxylic acids and subsequent intramolecular cyclizations has been developed. The key features of this work include: the first example of transition-metal-free decarboxylative amidation of α-oxocarboxylic acids with ortho-substituted amines, realization of intramolecular cyclization of amides employing nucleophiles that have previously been unexplored, mechanistic investigation of an unprecedented K2S2O8 promoted amide formation and its subsequent intramolecular cyclizations, and application to the synthesis of a best-selling marketed drug.

Graphical abstract: Formation of amides, their intramolecular reactions for the synthesis of N-heterocycles, and preparation of a marketed drug, sildenafil: a comprehensive coverage

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Article information


Submitted
20 May 2016
Accepted
13 Jul 2016
First published
13 Jul 2016

Chem. Commun., 2016,52, 10245-10248
Article type
Communication

Formation of amides, their intramolecular reactions for the synthesis of N-heterocycles, and preparation of a marketed drug, sildenafil: a comprehensive coverage

J. K. Laha, K. V. Patel, K. S. S. Tummalapalli and N. Dayal, Chem. Commun., 2016, 52, 10245
DOI: 10.1039/C6CC04259G

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