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

Wayland E Noland, Nicholas P. Lanzatella, Lakshmanan Venkatraman, Nicholas F. Anderson, Glen C. Gullickson

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

(Chemical Equation Presented) 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 MnO2 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.

Original languageEnglish (US)
Pages (from-to)1154-1176
Number of pages23
JournalJournal of Heterocyclic Chemistry
Volume46
Issue number6
DOIs
StatePublished - Nov 1 2009

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