Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling

Huy H. Nguyen; Mark J. Kurth

doi:10.1021/ol303314x

Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling

Huy H. Nguyen, Mark J. Kurth

Chemistry

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57 Scopus citations

Abstract

A variety of N-aryl β-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (μW) assisted intramolecular arene-alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkoxy-and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.

Original language	English (US)
Pages (from-to)	362-365
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	2
DOIs	https://doi.org/10.1021/ol303314x
State	Published - Jan 18 2013

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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10.1021/ol303314x

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abstract = "A variety of N-aryl β-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (μW) assisted intramolecular arene-alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkoxy-and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.",

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AB - A variety of N-aryl β-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (μW) assisted intramolecular arene-alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkoxy-and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.

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Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling

Abstract

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