80117-79-9Relevant academic research and scientific papers
SYNTHESIS OF 3-SUBSTITUTED 4-METHYLMERCAPTO- AND 4-AMINOPYRAZOLOPYRIMIDINES AND THEIR RIBOSIDES
Bulychev, Yu. N.,Korbukh, I. A.,Preobrazhenskaya, M. N.
, p. 210 - 215 (2007/10/02)
3-Cyano-4-methylmercaptopyrazolopyrimidine, fusion of which with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose gave its per-O-acetylated 1-β-D-ribofuranoside in 61percent yield, was synthesized from 3,4-dicyano-5-aminopyrazole.O-Deacetylation of the per-O-acetylated 1-β-D-ribofuranoside was carried out by the action of 1percent HCl in methanol. New pyrazolopyrimidines were obtained by the reaction of 3-cyano-4-methylmercaptopyrazolopyrimidine and its 1-riboside, as well as 3-cyano-4-aminopyrazolopyrimidine, with a number of nucleophilic reagents.The cytotoxic activities of the compounds obtained were studied.
REACTION OF 4-CYANO-5-AMINOPYRAZOLE AND 3,4-DICYANO-5-AMINOPYRAZOLE WITH DIMETHYLFORMAMIDE DIETHYLACETAL
Bulychev, Yu. N.,Korbukh, I. A.,Preobrazhenskaya, M. N.,Chernyshov, A. I.,Esipov, S. E.
, p. 215 - 221 (2007/10/02)
The condensation of 4-cyano-5-aminopyrazole or 3,4-dicyano-5-aminopyrazole with dimethylformamide diethylacetal was studied.It was shown that, in addition to the formation of dimethylaminomethyleneamino derivatives, alkylation of the pyrazole ring occurs under severe conditions without a solvent.Only the corresponding formamidino derivatives are formed when the same reactions are carried out in methanol under milder conditions.The site of addition of an ethyl group to the pyrazole ring in the N-alkyl derivatives obtained was established by 13C NMR and PMR spectroscopy.The possibility of the synthesis of 4-amino- or 4-methylmercaptopyrazolopyrimidines by cyclization of the ortho position was demonstrated for the first time.
