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Title: Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines
Authors: Dotsenko, V. V.
Доценко, В. В.
Keywords: Aldehyde derivative;Carbene;Carbonyl derivative;Cyanide;Cyclohexane derivative;Pyrazolopyrimidine derivative;Quinazoline derivative;Synthesis
Issue Date: 2016
Publisher: Royal Society of Chemistry
Citation: Kolosov, M.A., Beloborodov, D.A., Orlov, V.D., Dotsenko, V.V. Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-: A] pyrimidines // New Journal of Chemistry. - 2016. - Volume 40. - Issue 9. - Pages 7573-7579
Series/Report no.: New Journal of Chemistry
Abstract: The Biginelli-type reaction of 5-amino-3-arylpyrazole-4-carbonitriles with aldehydes and 1,3-dicarbonyl compounds was studied in detail. We found that the reaction requires no catalysts and proceeds in boiling DMF to give 2-aryl-6-RC(O)-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carbonitriles in good yields. The reaction of aminopyrazoles with dicarbonyls leading to 6-unsubstituted pyrazolo[1,5-a]pyrimidines proceeds competitively and becomes the dominant process under acid-promoted conditions. 2-Aryl-8-oxo-4,5,6,7,8,9-hexahydropyrazolo[5,1-b]quinazolin-3-carbonitriles were obtained under catalyst-free conditions in up to 80% yields starting from 5-amino-3-arylpyrazole-4-carbonitriles, aldehydes and 1,3-cyclohexanedione
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