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Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles

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Abstract

We report a silver-catalyzed hydroalkoxylation of C2-alkynyl quinazolinones to prepare a series of novel quinazolinone-fused eight-membered N,O-heterocycles in good-to-excellent yields through a selective 8-endo-dig cyclization. Mechanistic studies revealed that the silver catalyst might aid bidentate coordination of an imine group and alkyne to facilitate 8-endo-dig cyclization to afford eight-membered N,O-heterocycles. Also, the proposed bimetal silver intermediates might promote hydroalkoxylation rapidly for quinazolinones bearing terminal alkynes at the C2-position. Biological evaluations revealed that most of the designed quinazolinone-fused eight-membered N,O-heterocycles inhibited nitric-oxide generation significantly in lipopolysaccharide-stimulated RAW264.7 cells and displayed their bioactivity as potentially good anti-inflammatory agents.

Graphical abstract: Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles

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Article information


Submitted
10 Apr 2020
Accepted
17 Jun 2020
First published
18 Jun 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Silver(I)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles

X. Kong, X. Guo, Z. Gu, L. Wei, L. Liu, D. Mo, C. Pan and G. Su, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00437E

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