C-3 functionalization of indole derivatives with isoquinolines

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Abstract

The literature on the syntheses of substituted 1-(indol-3-yl)-1,2,3,4-tetrahydroisoquinoline derivatives is reviewed. Two main synthetic procedures have been applied for these syntheses. One is cross-dehydrogenative coupling, which can furnish various C-3 functionalized indoles; oxidants and/or catalysts are usually needed. Another convenient synthetic method is the aza-Friedel-Crafts alkylation of indole derivatives with dihydroisoquinoline, the main advantage of this being the direct catalyst-free coupling under mild experimental conditions. The review also considers miscellaneous reactions, where the isoquinoline skeleton is achieved in one of the final steps of the synthesis.

Original languageEnglish
Pages (from-to)2038-2054
Number of pages17
JournalCurrent Organic Chemistry
Volume20
Issue number20
DOIs
Publication statusPublished - Sep 1 2016

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Keywords

  • Aza-Friedel-Crafts alkylation
  • Cross-dehydrogenative coupling
  • Indole
  • Isoquinoline
  • β-carboline

ASJC Scopus subject areas

  • Organic Chemistry

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