Microwave-assisted facile construction of quinoxalinone and benzimidazopyrazinone derivatives via two paths of post-Ugi cascade reaction

Mol Divers. 2019 Feb;23(1):137-145. doi: 10.1007/s11030-018-9855-y. Epub 2018 Aug 2.

Abstract

A facile and efficient route to synthesize quinoxalinone and benzimidazopyrazinone was developed via two paths of a post-Ugi cascade reaction. By simply alternating the order of nucleophilic substitution reactions, both heterocycles could be accessed selectively from the same Ugi adduct. Microwave-assisted synthesis protocol provided these compounds with one purification procedure for three steps. These two scaffolds with more possible spaces for further modifications provide great benefit toward combinatorial and medicinal chemistry campaigns.

Keywords: Benzimidazopyrazinone; MCRs; Microwave irradiation; Nucleophilic substitution reaction; Quinoxalinone.

MeSH terms

  • Combinatorial Chemistry Techniques
  • Microwaves
  • Pyrazines / chemical synthesis*
  • Quinoxalines / chemical synthesis*

Substances

  • Pyrazines
  • Quinoxalines