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Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates
Author(s) -
Kim Saegun,
Jeoung Daeun,
Kim Kunyoung,
Lee Seok Beom,
Lee Suk Hun,
Park Min Seo,
Ghosh Prithwish,
Mishra Neeraj Kumar,
Hong Suckchang,
Kim In Su
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001128
Subject(s) - nitrene , chemistry , aryl , combinatorial chemistry , rhodium , functional group , surface modification , stereochemistry , catalysis , organic chemistry , alkyl , polymer
The site‐selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)‐catalyzed C–H amidation of 2‐aryl quinazolin‐4(3 H )‐ones with a range of nitrene surrogates including dioxazolones, organic azides, and N ‐methoxyamides. Complete site‐selectivity and functional group tolerance are observed. Notably, the large‐scale reaction and late‐stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.
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