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Paper | Regular issue | Vol 53, No. 11, 2000, pp.2363-2377
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8954
New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2-Alkylthioquinazolines, as well as Their Hetero Analogues

Margit Gruner,* Matthias Rehwald, Katrin Eckert, and Karl Gewald

*Institut of Organic Chemistry, Technical University Dresden, D-01062 Dresden, Germany


N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thio-cyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-4-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with ena-minocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subse-quent treatment of the intermediates with amines.