Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Abstract A metal-free oxidative C(sp 3 )–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1 H )-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1 H )-ones in...

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Bibliographic Details
Published in:Synlett 2018-04, Vol.29 (7), p.912-917
Main Authors: Rezaei, Narjes, Sheikhi, Ehsan, Ranjbar, Parviz Rashidi
Format: Article
Language:English
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Summary:Abstract A metal-free oxidative C(sp 3 )–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1 H )-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1 H )-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1591544