In Situ vinylpyrrole synthesis. Diels-alder reactions with maleimides to give tetrahydroindoles

Wayland E Noland, Nicholas P. Lanzatella, Elena P. Sizova, Lakshmanan Venkatraman, Oleg V. Afanasyev

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)503-534
Number of pages32
JournalJournal of Heterocyclic Chemistry
Volume46
Issue number3
DOIs
StatePublished - May 1 2009

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