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Paper | Regular issue | Vol 31, No. 12, 1990, pp.2163-2172
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5562
Synthesis of Aza Analogs of Amrinone

Baldev Singh* and George Y. Lesher

*Department of Medical Chemistry, Sterling Research Group, Rensselaer, New York 12144, U.S.A.


The aldol condensation product (4) of 4-acetylpyridine (2) and diethyl mesoxalate (3) was converted to pyridazinecarboxylic acid hydrazide (6). Curtius reaction of 6 gave aminopyridazinones (7). The condensation of (4-pyridinyl)glyoxal (17) with aminomalonamide (18) which was transformed to aminopyrazinone (19) by the Hofmann raction. Curtius reaction of 1,2,4-triazinone-5-carboxylic acid (21b) gave aminotriazinone (22). Demethylation of methoxypyrimidine (29) prepared from methyl 2-methoxyformylacetate (25) and isonicotinamidine (26) gave pyrimidinol (30).