NEW SYNTHESIS OF SUBSTITUTED 4-AMINO-QUIN AZOLINES AND THEIR HETEROANALOGS

N-Chloracetyl-anthranilonitriles react with potassium thiocyanate in t he presence of alcohol to the (4-amino-quinazolin-2-yl-thio)-acetic ac id ester (5). In the presence of water or primary amine the acetic aci d derivative (6) or the acetic acid amide derivatives (7) are obtained . 2,4-Diamino-quinazolines (8) arise if vigorous reaction conditions a re employed. With 2-chloracetylamino-cyclopent-1-en-carbonitrile as st arting material the pyrimidines (11) are formed from the reaction with potassium thiocyanate. Analogously, (4-pyrimidyl-2-yl-seleno)-acetic acid ester (12) and (thiazolo[4,5d]pyrimid-2-yl-seleno)-acetic acid de rivatives (16)can be prepared with potassium selenocyanate. N-Chlorace tyl derivatives of 5-membered heterocycles with enamino-nitrile struct ure (13, 15, 18, 20) react with potassium thiocyanate to yield thieno[ 2,3-d]-, thiazolo[4,5-d]-, pyrrolo[2,3-d]-, furo[2,3-d]and pyrazolo[4, 3-d]pyrimidines (14, 16, 19a, 19b, 21).