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

doi:10.1002/jhet.198

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

22 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 language	English (US)
Pages (from-to)	1154-1176
Number of pages	23
Journal	Journal of Heterocyclic Chemistry
Volume	46
Issue number	6
DOIs	https://doi.org/10.1002/jhet.198
State	Published - Nov 2009

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title = "Access to indoles via Diels-Alder reactions of 2-vinylpyrroles with maleimides",

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.",

author = "Noland, {Wayland E} and Lanzatella, {Nicholas P.} and Lakshmanan Venkatraman and Anderson, {Nicholas F.} and Gullickson, {Glen C.}",

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AU - Noland, Wayland E

AU - Lanzatella, Nicholas P.

AU - Venkatraman, Lakshmanan

AU - Anderson, Nicholas F.

AU - Gullickson, Glen C.

PY - 2009/11

Y1 - 2009/11

N2 - (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.

AB - (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.

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IS - 6

ER -

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

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