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http://dx.doi.org/10.5012/bkcs.2009.30.3.561

Synthesis of Some Imidazopyrazolopyrimidines, Pyrazolopyrimidopyrimidines and Pyrazolopyrimidothiazines  

Elkhawaga, A.M. (Chemistry Department, Faculty of Science, Assiut University)
Kamal El-Dean, A.M. (Chemistry Department, Faculty of Science, Assiut University)
Radwan, M. (Chemistry Department, Faculty of Science, Assiut University)
Ahmed, M.M. (Chemistry Department, Faculty of Science, Assiut University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.3, 2009 , pp. 561-566 More about this Journal
Abstract
Chloroacylation of 3-amino-2-phenylpyrazole-4-carboxamide (2) using chloroacetyl-(propionyl) chloride affording 6-chloromethyl(ethyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4[5H]-one (3) or (6). Chlorine atom in compound (3) or (6) underwent nucleophilic substitution reaction with primary or secondary amines to give 6-alkyl(aryl)aminomethyl(ethyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4[5H]-one (4a-g,7a-f). When arylaminomethyl( ethyl)pyrazolopyrimidine was treated with formaline (30%) solution in ethanol, underwent Mannich reaction to afford imidazopyrazolopyrimidines (5a-e) and pyrazolopyrimidopyrimidines (8a-e). Chloromethylpyrimidine derivative 3 was converted into the corresponding mercaptomethylpyrazolopyrimidene 9, Which cyclized using bromomalononitrile or phenacyl bromide into pyrazolopyrimidothiazine 11,12.
Keywords
Synthesis, Pyrazolopyrimidines; Imidazopyrazolopyrimidines; Pyrimidopyrazolopyrimidines; Pyrimidopyrazolothiazines;
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