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Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

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Abstract

Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C–C and C–N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C–C and C–N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.

Graphical abstract: Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

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Supplementary files

Article information


Submitted
11 Dec 2019
Accepted
04 Feb 2020
First published
06 Feb 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

S. K. Roy, A. Purkait, S. M. T. Aziz and C. K. Jana, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09616G

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