SYNTHESIS OF FUSED PYRIMIDINONES BY REACTION OF AMINOARENE-CARBOXAMIDE WITH ESTERS - PREPARATION OF PYRROLO[2,3-D]PYRIMIDINONES, THIENO[2,3-D]PYRIMIDINONES, ISOXAZOLO[5,4-D]PYRIMIDINONES, AND 1,2,3-TRIAZOLO[4,5-D]PYRIMIDINONES, AND PYRROLO[2,3-D]QUINAZOLONES, THIENO[2,3-D]QUINAZOLONES, ISOXAZOLO[5,4-D]QUINAZOLONES AND 1,2,3-TRIAZOLO[4,5-D]QUINAZOLONES
A. Miyashita et al., SYNTHESIS OF FUSED PYRIMIDINONES BY REACTION OF AMINOARENE-CARBOXAMIDE WITH ESTERS - PREPARATION OF PYRROLO[2,3-D]PYRIMIDINONES, THIENO[2,3-D]PYRIMIDINONES, ISOXAZOLO[5,4-D]PYRIMIDINONES, AND 1,2,3-TRIAZOLO[4,5-D]PYRIMIDINONES, AND PYRROLO[2,3-D]QUINAZOLONES, THIENO[2,3-D]QUINAZOLONES, ISOXAZOLO[5,4-D]QUINAZOLONES AND 1,2,3-TRIAZOLO[4,5-D]QUINAZOLONES, Heterocycles, 42(2), 1996, pp. 691-699
Several fused pyrimidinones were synthesized by reaction of aminoarene
carboxamide with esters in moderate to good yields. In the presence of
sodium ethoxide, treatments of 2-amino-1-phenyl-3-pyrrolecarboxamide(
4, 5, and 6), 2-amino-3-thiophene-carboxamide (14), 3-amino-4-isoxazol
ecarboxamide (10 and 11), 4-amino-1,2,3-triazole-5-carboxamide (16), a
nd o-aminobenzamide (18) with esters (3) such as ethyl formate (3a) an
d ethyl acetate (3b) led to the corresponding pyrrolo[2,3-d]- (7, 8, a
nd 9), and thieno[2,3-d]pyrimidin-4(3H)-ones (15), isoxazolo[5,4-d]pyr
imidin-4(5H)-ones (12 and 13), 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-on
es (17), and 4(3H)-quinazolones (19), respectively.