Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates

Thomas J. Greshock; Raymond L. Funk

doi:10.1021/ja060282o

Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates

Thomas J. Greshock, Raymond L. Funk

Chemistry

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

72 Scopus citations

Abstract

A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac₂O, NEt₃, 130 °C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

Original language	English (US)
Pages (from-to)	4946-4947
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	15
DOIs	https://doi.org/10.1021/ja060282o
State	Published - Apr 19 2006

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja060282o

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abstract = "A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 °C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.",

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N2 - A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 °C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

AB - A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 °C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

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