Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones

2-methylthio-2-imidazoline and 2-methylthio-1,4,5,6-tetrahydro-2-pyrimidine amidated 2-chloro-3-pyridine- and 2-chloro-3-pyrazinecarbonyl chlorides. The products reacted with aromatic amines forming a series of tricyclic, linearly fused -aryl pyrimidones. Included among these pyrimidones were 10-aryl-2,3-dihydroimidazo[1,2-]pyrido[2,3-]pyrimidin-5(10)-ones, 11-aryl-2,3,4,11-tetrahydropyrido-[2,3-]pyrimido[1,2-]pyrimidin-6(6)-ones, 10-aryl-2,3-dihydroimidazo[1,2-]pyrazino[2,3-]pyrimidin-5(10)-ones and 11-aryl-2,3,4,11-tetrahydropyrimido-[1,2-]pyrazino[2,3-]pyrimidin-6(6)-ones. 4,5,6,7-Tetrahydro-2-(mythylthio)-1-1,3-diazepine amidated the ethyl hydrogen carbonate of 2-(phenylamino)-3-pyridinecarboxylic acid, forming 12-phenyl-2,3,4,5-tetrahydropyrido[2',3':4,5]pyrimido[1,2-][1,3]diazepine-7(12)-one. A single crystal X-ray analysis and an unambiguous synthesis established the structure of the linearly fused isomer 10-phenyl-2,3-dihydroimidazo[1,2-]pyrido[2,3-]pyrimidin-5(10)-one.

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Author Andrew T. McPhail Chemistry