The cyclocondensation of substituted 5-aminopyrazoles with benzylidene acetone leads to the regioselective synthesis of dihydropyrazolo[1,5-a]pyrimidines and dihydropyrazolo[3,4-b]pyridines containing a methyl group in the six-membered heterocycle. Compounds of both these groups readily undergo carbo[3 + 3] cyclo-condensation with chalcones in butanol under alkaline catalysis conditions and upon heating to give aryl-substituted tetrahydropyrazolo[1,5-b]quinazolines and tetrahydropyrazolo[4,5-b]quinolines. Ultrasonic initiation of these reactions leads to enhanced rate and higher yield of the desired products.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 698-705, April, 2012.
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Orlov, V.D., Sidorenko, D.Y. Carbo[3 + 3] cyclocondensation reactions. A new method for the synthesis of tetrahydropyrazolo[1,5-b]quinazolines and tetrahydropyrazolo[4,5-b]quinolines. Chem Heterocycl Comp 48, 650–657 (2012). https://doi.org/10.1007/s10593-012-1039-6
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DOI: https://doi.org/10.1007/s10593-012-1039-6