Synthesis of fused pyrimidinones by reaction of aminoarene-carboxamide with esters; Preparation of pyrrolo[2,3-d]-, thieno[2,3-d]-, isoxazolo[5,4-d]- and 1,2,3-triazolo[4,5-d]pyrimidinones, and quinazolones

Article abstract of DOI:10.3987/COM-95-S75

Several fused pyrimidinones were synthesized by reaction of aminoarenecarboxamide with esters in moderate to good yields. In the presence of sodium ethoxide, treatments of 2-amino-l-phenyl-3-pyrrolecarboxamide(4, 5, and 6), 2-amino-3-thiophenecarboxamide (14), 3-amino-4-isoxazolecarboxamide (10 and 11), 4-amino-1,2,3-triazole-5-carboxamide (16), and o-aminobenzamide (18) with esters (3) such as ethyl formate (3a) and ethyl acetate (3b) led to the corresponding pyrrolo[2,3-d]- (7, 8, and 9), and thieno[2,3-d]pyrimidin-4(3H)-ones (15), isoxazolo[5,4-d]pyrimidin-4(5H)-ones (12 and 13), 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-ones (17), and 4(3H)-quinazolones (19), respectively.