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Access to indoles via Diels-Alder reactions of 2-vinylpyrroles with maleimides

✍ Scribed by Wayland E. Noland; Nicholas P. Lanzatella; Lakshmanan Venkatraman; Nicholas F. Anderson; Glen C. Gullickson

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

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✦ Synopsis

Abstract

magnified image Variously substituted 2‐vinylpyrroles underwent an endo‐addition [4+2] cycloaddition reaction with maleimides followed by a spontaneous highly diastereoselective (93–98% de) isomerization to give tetrahydroindoles in moderate to excellent yield. Treatment with activated MnO~2~ in refluxing toluene provided the corresponding indoles in moderate to good yield. This highly convergent methodology for formation of indoles is versatile and the starting materials are conveniently prepared. J. Heterocyclic Chem., (2009).

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