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In situ vinylpyrrole synthesis. Diels-Alder reactions with maleimides to give tetrahydroindoles

✍ Scribed by Wayland E. Noland; Nicholas P. Lanzatella; Elena P. Sizova; Lakshmanan Venkatraman; Oleg V. Afanasyev

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
518 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

A series of 108 tetrahydroindoles has been prepared by a one‐pot synthesis from 2‐alkylpyrroles, cyclic ketones, maleimides, and an acid catalyst. A 5‐vinylpyrrole is formed by an acid‐catalyzed condensation of a 2‐alkyl‐substituted pyrrole with a ketone, which is subsequently trapped in situ by a maleimide in a predominantly endo‐addition Diels‐Alder reaction. Isomerization of the double bond into the pyrrole ring gives a tetrahydroindole with predominant cis‐fusion of the cycloalkane ring. J. Heterocyclic Chem., 46, 503 (2009).

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