Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization

Po Hsin Eric Yao, Sunil Kumar, Yu Li Liu, Chiu Ping Fang, Chia Chen Liu, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds. An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray analysis and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney d-amino acid oxidase (pkDAO).

Original languageEnglish
Pages (from-to)271-275
Number of pages5
JournalACS Combinatorial Science
Volume19
Issue number4
DOIs
StatePublished - 10 Apr 2017

Keywords

  • Knoevenagel condensation
  • coumarin
  • diversity-oriented synthesis
  • one-pot synthesis
  • pkDAO activity

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