Palladium-Catalyzed Regioselective Synthesis of 1,2-Fused Indole-Diazepines via [5+2] Annulation of o-Indoloanilines with Alkynes

Tushar Ulhas Thikekar, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

An efficient and regioselective palladium(II)-catalyzed [5+2] annulation of unprotected o-indoloanilines with internal alkynes under microwave irradiation has been explored. The diverse imine-containing 1,2-fused indole[1,7-a]diazepines are constructed in moderate to excellent yields. The mechanistic pathway shows pivalic acid and molecular oxygen to play crucial roles for the regeneration of highly active electrophilic palladium species in the catalytic cycle. (Figure presented.).

Original languageEnglish
Pages (from-to)3388-3396
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number19
DOIs
StatePublished - 4 Oct 2017

Keywords

  • [5+2] annulation
  • chemoselective synthesis
  • indole[1,7-a]diazepines
  • microwave reaction
  • regioselective synthesis

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