Ketone-derived 2,3-dihydroquinazolinones in N-heteroarene C-H alkylation via C-C bond scission under oxidative metal catalysis

Chem Commun (Camb). 2022 Nov 29;58(95):13202-13205. doi: 10.1039/d2cc04947c.

Abstract

A silver-catalysed oxidative sp2 C-H alkylation of N-heteroarenes with ketone-derived 2,3-dihydroquinazolinones at room temperature is developed. The combination of a metal catalyst and perdisulfate oxidant promotes the rarely explored thermal activation of pre-aromatic 2,3-dihydroquinazolinone to generate an alkyl radical, supported by mechanistic studies. In addition to the broad scope, good functionality tolerance, late stage functionalization of APIs, and synthesis of a novel Papaverine analogue, the utilization of an N-heteroarene C-H bond and ketone as a non-trivial alkyl radical source represents the salient feature of this method.

MeSH terms

  • Alkylation
  • Catalysis
  • Ketones*
  • Metals*
  • Oxidation-Reduction
  • Oxidative Stress

Substances

  • Ketones
  • Metals