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Microwave‐Assisted Synthesis of Benzimidazole‐Linked Indoline and Indole Hybrids from C‐2 Linked ( o ‐Aminobenzyl)benzimidazoles
Author(s) -
Lee YunTa,
Chiu FengYu,
Barve Indrajeet J.,
Sun ChungMing
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701140
Subject(s) - benzimidazole , chemistry , indoline , moiety , intramolecular force , indole test , combinatorial chemistry , imine , condensation , stereochemistry , organic chemistry , catalysis , physics , thermodynamics
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.