Collect. Czech. Chem. Commun.
1993, 58, 1133-1150
https://doi.org/10.1135/cccc19931133
Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones
Richard Friarya, Andrew T. McPhailb and Vera Seidla
a Schering-Plough Research Institute, Kenilworth, New Jersey 07033-0539, U.S.A.
b Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27706, U.S.A.
Abstract
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 N-aryl pyrimidones. Included among these pyrimidones were 10-aryl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-ones, 11-aryl-2,3,4,11-tetrahydropyrido-[2,3-d]pyrimido[1,2-a]pyrimidin-6(6H)-ones, 10-aryl-2,3-dihydroimidazo[1,2-a]pyrazino[2,3-d]pyrimidin-5(10H)-ones and 11-aryl-2,3,4,11-tetrahydropyrimido-[1,2-a]pyrazino[2,3-d]pyrimidin-6(6H)-ones. 4,5,6,7-Tetrahydro-2-(mythylthio)-1H-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-a][1,3]diazepine-7(12H)-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-a]pyrido[2,3-d]pyrimidin-5(10H)-one.
