Literature DB >> 16608316

Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.

Thomas J Greshock1, Raymond L Funk.   

Abstract

A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-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 degrees 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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Year:  2006        PMID： 16608316      PMCID： PMC2597544          DOI： 10.1021/ja060282o

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  4 in total

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  4 in total
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Review 9.  Continuous Flow Synthesis of Heterocycles: A Recent Update on the Flow Synthesis of Indoles.

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  9 in total

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