Synthesis of indole and related compounds from halo-nitroaromatics

Takao Sakamoto, Yoshinori Kondo, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

5,7-Dimethyl-6-azaindole was synthesized by treatment of 3-amino-2,6-dimethyl-4-pyridineacetaldehyde diethyl acetal with hydrochloric acid in boiling ethanol. According to the similar manner, indole and ethyl 4-indolecarboxylate were obtained from the corresponding 2-aminophenylacetaldehyde derivatives in satisfactory yields. The starting materials were easily prepared by palladium-catalyzed cross-coupling reaction of o-halonitroaromatics with trimethylsilylacetylene followed by the reaction with sodium ethoxide and catalytic reduction of the o-nitro group.

Original languageEnglish
Pages (from-to)1347-1350
Number of pages4
JournalHeterocycles
Volume22
Issue number6
DOIs
Publication statusPublished - 1984 Jan 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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