Issue 95, 2022

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
07 sep 2022
Accepted
25 okt 2022
First published
26 okt 2022

Chem. Commun., 2022,58, 13202-13205

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

P. P. Mondal, A. Pal, A. K. Prakash and B. Sahoo, Chem. Commun., 2022, 58, 13202 DOI: 10.1039/D2CC04947C

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