A Novel Mechanistic Study on Ultrasound-Assisted, One-Pot Synthesis of Functionalized Benzimidazo[2,1-b]quinazolin-1(1H)-ones

Li Hsun Chen, Tsai Wen Chung, Bharat D. Narhe, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Ultrasound-assisted synthesis of benzimidazo[2,1-b]quinazolin-1(1H)-ones was achieved via piperidine-catalyzed three-component reaction of 2-aminobenzimidazoles, an aromatic aldehyde, and 1,3-dione in aqueous isopropanol. This mechanism was first suspected following our identification of unusual reaction intermediates in a one-pot reaction. An unprecedented coupling reaction, it involved a nucleophilic attack by 2-aminobenzimidazole on in situ generated Michael adduct, followed by electrocyclic ring formation reaction. In contrast to the commonly accepted mechanism, that the direct reaction of 2-amino benzimidazole with a Knoevenagel adduct cannot deliver target compounds.

Original languageEnglish
Pages (from-to)162-169
Number of pages8
JournalACS Combinatorial Science
Volume18
Issue number3
DOIs
StatePublished - 14 Mar 2016

Keywords

  • benzimidazo[2,1-b]quinazolin-1(1H)-ones
  • multicomponent reaction
  • ultrasonication

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