Reactions of o-aminonitriles with isocyanates. 2. A facile synthesis of imidazo[1,2-c]quinazoline-2,5-(3H,6H)dione

Anthranilonitrile reacts with ethyl isocyanatoacetate to form 2-(3-ethoxycarbonylmethylureido)benzonitrile (3b) which, upon heating, or treatment with a base, undergoes a double cyclization to yield imidazo1,2-c]-quinazoline-2,5-(3H,6H)dione ( 5 ) in excellent yield. In the presence of acid, 3b is converted into 1,4-dihydro-2,4-dioxo-3-(2H)quinazolineacetic acid ( 11 ), or its ethyl ester ( 10 ). The action of concentrated sulfuric acid converts the adduct 13 of anthranilic acid and ethyl isocyanatoacetate into 2-ethoxycarbonyl-methylamino-4H-3,1 -benzoxazin-4-one ( 14 ).