Transformations of Dialkyl Acetone-1,3-dicarboxylates via Their Dimethylaminomethylidene Derivatives Into 1-substituted 4-ethoxycarbonyl-5-(ethoxycarbonylmethyl)pyrazoles, 7-amino-2-ethoxycarbonyl-1H, 2H-pyrazolo2,3-cpyrimidin-5-one, 4-hydroxypyridin-2(1H)-ones and 6-substituted 3-benzoylamino-2,5-dioxo-5,6-dihydro-2H-pyrano3,2-cpyridine-8-carboxylates

摘要

Diethyl 1-dimethylamino-3-oxobut-1-ene-2,4-dicarboxylate(2a),prepared from diethyl acetone-1,3-dicarboxylate and N,N-dimethylformamide dimethylacetal(DMFDMA),was transformed with hydrazines 3a-g into 1-susbtituted 4-et-hoxycarbonyl-5-(ethoxycarbonylmethyl)pyrazoles 5a-g,with aminoguanidine(6)into 7-amino-2-ethoxycarbonyl-1H,2H-pyrazolo2,3-cpyrimidin-5-one(9),and with amines 10a-k into 4-hydroxypyridin-2(1H)-ones 11a-k.Compounds 11 were treated with methyl(Z)-2-benzoylamino-3-dimethylaminopropenoate(12)to give 6-substituted 3-ben-zoylamino-2,5-dioxo-5,6-dihydro-2H-pyrano3,2-cpyridine-8-carboxylates 14,while in the reaction with methyl 3-di-methylamino-2-(methoxycarbonyl)propenoate(15)decarboxylation of one of the ester groups took place producing alkyl(E)-1-alkyl-4-hydroxy-5-(3-methoxy-3-oxoprop-1-enyl)-6-oxo-1,6-dihydropyridine-3-carboxylates 17.