One-Pot Synthesis of Spiro-2H-pyrroles fromN-Propargylic beta-Enaminones

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KARADENİZ E., ZORA M.

SYNLETT, vol.30, no.10, pp.1231-1236, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 30 Issue: 10
  • Publication Date: 2019
  • Doi Number: 10.1055/s-0037-1611816
  • Journal Name: SYNLETT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1231-1236
  • Keywords: pyrrole, 2H-pyrrole, N-propargylic beta-enaminones, spiro compound, nucleophilic cyclization, benzylic C-H oxidation, BENZYLIC OXIDATION, ENANTIOSELECTIVE SYNTHESIS, MEDICINAL CHEMISTRY, FACILE, SPIRO, FLUORINE, PYRROLES, DEAROMATIZATION, DERIVATIVES, IRBESARTAN
  • Middle East Technical University Affiliated: Yes

Abstract

A simple and general one-pot method for the synthesis of spiro-2 H -pyrroles has been developed. Initially, cyclohexane-embedded -enaminones with internal alkyne functionality were synthesized by conjugate addition of 1-ethynylcyclohexylamine to ,-alkynic ketones, followed by palladium-catalyzed coupling of the resulting N -propargylic -enaminones with aryl iodides. When subjected to basic conditions, the cyclohexane-embedded -enaminones with internal alkyne functionality underwent tandem nucleophilic cyclization and benzylic C-H oxidation to furnish 3,4-diaryloyl-1-azaspiro[4.5]deca-1,3-diene derivatives in good yields.