biostudies-literatureGreshock TJNIGMS NIH HHS4946-7https://www.ebi.ac.uk/biostudies/studies/S-EPMC2597544biostudies-literatureUnknown128(15)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.Journal of the American Chemical SocietySynthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.PMC2597544R01 GM028663-24GM28533R01 GM028663R01 GM028663-27R01 GM028663-28R01 GM028663-25R01 GM028663-26Greshock TJFunk RLfalseSynthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.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.2006-01-01T00:00:00Z2006 Apr2025-04-05T15:11:20.837Z2019-03-27T00:19:43ZS-EPMC25975441660831610.1021/ja060282o