56406-26-9Relevant articles and documents
Tricyclic Heteroaromatic Systems Containing a Bridgehead Nitrogen Atom. Part 3. Triazolopyrazolopyrimidines, Tetrazolopyrazolopyrimidines and Pyrimidopyrazolotriazines
Golec, Julian M. C.,Scrowston, Richard M.,Dunleavy, Michael
, p. 239 - 244 (2007/10/02)
6-Phenyl-1H-pyrazolopyrimidin-3(2H)-one 16 has been prepared and converted into its 3-chloro 6, 3-thioxo 17 and 3-methylthio derivatives 9.Each of these could be converted into the 3-hydrazino derivative 3, cyclisation of which with carbon disulfide or triethyl orthoformate generated the fused 1,2,4-triazoles 23 and 20, respectively.Alternatively, the hydrazino derivative 3 gave a substituted hydrazide 26 or thiosemicarbazide 25, from which the 1,2,4-triazoles 21 and 22 respectively were obtained.The equilibrium between 3-azido-6-phenyl-1H-pyrazolopyrimidine 5 and 2-phenyl-9H-tetrazolopyrazolopyrimidine 27 was studied. 3-Diazo-4-methyl-6-phenyl-1H-pyrazolopyrimidine 29 was prepared by diazotisation of the corresponding amine 1 and converted into the 3-azido compound 4, which could not be cyclised to form a tetrazole.Finally, the diazo compound 29 readily formed the pyrimidopyrazolotriazine derivatives 32 and 33, when treated with pentane-2,4-dione and ethyl acetoacetate respectively.
Antiallergy agents. I. 1,6-dihydro-6-oxo-2-phenylpyrimidine-5-carboxylic acids and esters
Juby,Hudyma,Brown,et al.
, p. 263 - 269 (2007/10/08)
The synthesis of some 1,6-dihydro-6-oxo-2-phenylpyrimidine-5-carboxylic acids and esters with potent oral and intravenous antiallergic activity against passive cutaneous anaphylaxis in the rat is described. Requirements for high activity include a free NH group in the pyrimidinone nucleus and a small to medium size ortho alkoxy or alkenyloxy group on the phenyl ring. It is suggested that in the case of the highly active compounds hydrogen bonding occurs between a nitrogen of the pyrimidine ring and the ethereal oxygen. The nature of this bonding and its possible contribution to an optimum configuration for the molecules is discussed.