Microwave-Assisted Synthesis of Benzimidazole-Linked Indoline and Indole Hybrids from C-2 Linked (o-Aminobenzyl)benzimidazoles

Yun Ta Lee, Feng Yu Chiu, Indrajeet J. Barve, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

An efficient and novel synthesis of benzimidazole-linked indoline hybrids via an unconventional Pictet-Spengler-type condensation of C-2 linked (o-aminobenzyl)benzimidazoles with aldehydes and ketones under microwave irradiation has been explored. The key condensation step consists of acid-catalyzed imine generation followed by intramolecular C–C bond formation through unique reactivity of the benzimidazole moiety. The scope of this method is further extended to synthesize tetracyclic pyrroloindole benzimidazole-carboxylates through 2-carboxaldehydes. (Figure presented.).

Original languageEnglish
Pages (from-to)502-512
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number3
DOIs
StatePublished - 1 Feb 2018

Keywords

  • benzimidazole-linked indoles
  • benzimidazole-linked indolines
  • indoline synthesis
  • pyrroloindolebenzimidazole-carboxylates
  • unconventional Pictet–Spengler reaction

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