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2005
Fused pyrimidine derivatives
R 0515
Synthetic Studies on 3-Arylquinazolin-4-ones: Intramolecular Nucleophilic AroSubstitution Reaction of 2-Carboxamido-3-arylquinazolin-4-ones and Its
33- 168 matic
Application to the Synthesis of Secondary Aryl Amines. — A general synthesis of
title amides is based on the dehydration/cyclization of 2-carbamoylanilides (I) using
TmsCl. The resulting esters are converted to the corresponding amides by two methods.
The first one involves amidation of the ester by dimethylaluminum amide, the second
one involves conversion to thiol esters followed by Ag-mediated amidation. Optimized
conditions are found for the intramolecular substitution reaction of the 3-arylquinazolinones. Migration of the N3-aryl group is induced by action of NaH to afford the corresponding N,N-disubstituted amides (to be continued). — (FUWA, H.; KOBAYASHI,
T.; TOKITOH, T.; TORII, Y.; NATSUGARI*, H.; Tetrahedron 61 (2005) 17,
4297-4312; Grad. Sch. Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113, Japan; Eng.)
— Klein
2005
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