Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Ketene and Its Derivatives. LXXIII. Synthesis of Pyrido [1, 2-a]-pyrimidin-4-one and Pyrido [1, 2-a] sym-triazin-4-one Derivatives
TETSUZO KATOSHINICHI MASUDA
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1975 Volume 23 Issue 10 Pages 2251-2256

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Abstract
Ethyl N-(2-pyridyl) formimidate (Va) reacted with diketene to give 3-acetyl-4H-pyrido [1, 2-a] pyrimidin-4-one (VIIa) and ethyl 2-(2-pyridylaminomethylene) acetoacetate (VIIIa). Reaction of diketene with ethyl N-(2-pyridyl) acetimidate (Vb) and ethyl N-(2-pyridyl) propionimidate (Vc) afforded 4H-pyrido [1, 2-a] pyrimidine derivatives (VIIb and VIIc), respectively. Similarly 2-benzylideneaminopyridine (VIa) reacted with diketene to give 3-acetyl-4-hydroxy-2-phenyl-4H-pyrido-[1, 2-a] pyrimidine (XI). On the other hand, reaction of trimethylsilyl isocyanate with Va, Vb, and Vc gave rise to 4H-pyrido [1, 2-a]-sym-triazin-4-one derivatives (XIXa, XIXb, and XIXc), respectively. Reaction of phenyl isocyanate with VIa afforded 2, 3-diphenyl-4H-pyrido [1, 2-a]-sym-2, 3-dihydrotrazin-4-one (XX).
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