PIDA-mediated intramolecular oxidative C-N bond formation for the direct synthesis of quinoxalines from enaminones

RSC Adv. 2019 Mar 7;9(14):7718-7722. doi: 10.1039/c9ra01200a. eCollection 2019 Mar 6.

Abstract

A intramolecular oxidative C(sp2)-N bond formation mediated by hypervalent iodine(iii) to obtain quinoxalines from readily available N-(2-acetaminophenyl)enaminones was developed. A tandem process involving PIDA-mediated intramolecular condensation cyclization and a subsequent elimination was postulated, which was highly efficient and metal-free under mild conditions. Moreover, flexible structural modifications of quinoxalines bearing carbonyl groups are of interest for further transformations as building blocks in organic synthesis.