Reactions with 2-Aminonicotinic Acid, I Some 8-Aza Analogs of Quinazolinones and Derived Tricyclic Compounds

Article abstract of DOI:10.1007/BF00799933

The fusion of 2-acetamidonicotinic acid with o-toluidine, p-bromoaniline or o-chloroaniline afforded the corresponding 3-aryl-2-methyl-pyrido<2,3-d>pyrimidin-4(3H)-ones (4), the 8-aza analogs of 3-aryl-2-methyl-4-quinazolinones, alongside 2-aminonicotinic acid. 2-Methyl-3-(2-methylphenyl)-pyrido<2,3-d>pyrimidin-4(3H)-one (4a), the 8-aza analog of methaqualone, was converted to the 2-substituted styryl derivatives 6 by condensation with some aromatic aldehydes and to the tricyclic system, 10-aza-5,6-dihydro-3-hydroxy-5-(2-methylphenyl)-2-substituted-1H-pyrido<1,2-a>quinazoline-1,6-diones (8) by reaction with monosubstituted bis-2,4,6-trichlorophenyl malonates. - Keywords: 10-Aza-5,6-dihydro-3-hydroxy-5-(2-methylphenyl)-2-substituted-1H-pyrido<1,2-a>quinazoline-1,6-diones; Bis-2,4,6-trichlorophenyl malonates; 3H-Pyrido<2,3-d>pyrimidin-4-ones