Synthesis of new 2-vinylation products of indole via a michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles

Cavdar H., SARAÇOĞLU N.

JOURNAL OF ORGANIC CHEMISTRY, vol.71, no.20, pp.7793-7799, 2006 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 71 Issue: 20
  • Publication Date: 2006
  • Doi Number: 10.1021/jo061336f
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Page Numbers: pp.7793-7799
  • Ankara University Affiliated: No

Abstract

[GRAPHICS] Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels-Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.