Microwave-Assisted Multicomponent Synthesis of Dihydroquinoxalinones on Soluble Polymer Support

Prashant B. Dalvi, Shu Fen Lin, Vijaykumar Paike, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

A one-pot and two-step reaction of four components, including aldehydes, Fmoc-protected α-amino acid, isocyanide, and soluble polymer-supported 4-fluoro-3-amino benzoate ester, was developed for an efficient synthesis of dihydroquinoxalinones under microwave irradiation. Fmoc deprotection followed by intramolecular cyclization of the diamide gave a facile access to novel bicyclic quinoxalin-2-ones. On the basis of this approach, a new route to synthesize this privileged scaffold from the diamide intermediate was designed and accomplished with high yields. Use of multicomponent reaction (MCR) has been shown to display a good functional group tolerance, while the product isolation and purification is straightforward by precipitation and washings. Current library discusses the synthesis and diversification of 21 compounds produced using this strategy.

Original languageEnglish
Pages (from-to)421-425
Number of pages5
JournalACS Combinatorial Science
Volume17
Issue number7
DOIs
StatePublished - 13 Jul 2015

Keywords

  • dihydroquinoxalin-2-ones
  • microwave chemistry
  • multicomponent reaction (MCR)
  • soluble supported synthesis

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