Friedel-Crafts cyclization of 2-(3-indolythio)propionic acids. An unusual rearrangement leading to 4-sulfur-substituted tricyclic indoles

John Y.L. Chung, Robert A. Reamer, Paul J. Reider

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

The intramolecular Friedel-Crafts acylation of 2-(3-indolythio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3. A mechanism for its formation is proposed. This rearrangement also proceeded with good optical retention when a chiral substrate was used.

Original languageEnglish (US)
Pages (from-to)4717-4720
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number33
DOIs
StatePublished - Aug 11 1992
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • 4-thio-indoles
  • Friedel-Crafts acylation
  • rearrangement
  • thiopyrano-[4,3.2-c,d]indoles
  • tricyclic-indoles

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