Generation of N-(tert-butoxycarbonyl)indole-2,3-quinodimethane and its [4+2]-type cycloaddition

Fuyuhiko Inagaki; Masaya Mizutani; Norikazu Kuroda; Chisato Mukai

doi:10.1021/jo901325d

Generation of N-(tert-butoxycarbonyl)indole-2,3-quinodimethane and its [4+2]-type cycloaddition

J Org Chem. 2009 Aug 21;74(16):6402-5. doi: 10.1021/jo901325d.

Authors

Fuyuhiko Inagaki¹, Masaya Mizutani, Norikazu Kuroda, Chisato Mukai

Affiliation

¹ Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

PMID: 19621889
DOI: 10.1021/jo901325d

Abstract

The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K(2)CO(3) or Pd(2)(dba)(3) in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the corresponding tetrahydro- and dihydrocarbazole derivatives.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry
Alkynes / chemistry
Aniline Compounds / chemistry
Carbonates / chemistry
Indoles / chemical synthesis*
Indoles / chemistry*
Organometallic Compounds / chemistry
Potassium / chemistry

Substances

Alkenes
Alkynes
Aniline Compounds
Carbonates
Indoles
N-(tert-butoxycarbonyl)indole-2,3-quinodimethane
Organometallic Compounds
tris(dibenzylideneacetone)dipalladium
potassium carbonate
Potassium
aniline