Heat Versus Basic Conditions: Intramolecular Dehydro-Diels-Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles

Takayuki Kudoh, Syo Fujisawa, Megumi Kitamura, Akira Sakakura

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The intramolecular dehydro-Diels-Alder reaction of 1-indolyl-1,6-heptadiynes proceeds smoothly under rather mild heating conditions to give substituted carbazoles in moderate to good yields. The reaction of 7-aryl-1-indolyl-1,6-heptadiynes under heating gives the corresponding carbazoles chemoselectively in high yields, whereas the reaction under basic conditions gives naphthalenes as major products.

Original languageEnglish
Pages (from-to)2189-2193
Number of pages5
JournalSynlett
Volume28
Issue number16
DOIs
Publication statusPublished - Oct 4 2017

Keywords

  • carbazoles
  • chemoselectivity
  • dehydro-Diels-Alder reaction
  • indoles
  • intramolecular Diels-Alder reaction
  • naphthalenes

ASJC Scopus subject areas

  • Organic Chemistry

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