Facile Regioselective On-Water Synthesis of 4,7-Dihydropyrazolo[1,5-a]Pyrimidines and 4,7-Dihydro[1,2,4]Triazolo[1,5-a]Pyrimidines

Efficient and regioselective on-water synthesis of variously substituted 5-amino-4,7-dihydropyrazolo[1,5- a ]pyrimidine-6-carbonitriles and 5-amino-4,7-dihydro[1,2,4]triazolo[1,5- a ]pyrimidine-6-carbonitriles using 1,8-diazabicyclo[5.4.0]undec-7-ene as catalyst has been demonstrated. The reaction o...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-03, Vol.55 (3), p.246-253
Main Authors: Gol, Ravindra M., Khatri, Taslimahemad T., Barot, Vijaykumar M.
Format: Article
Language:English
Subjects:
Alkaloids
Amines
Aromatic compounds
Biochemistry
Chemistry
Chemistry and Materials Science
Genetic research
Heterocyclic compounds
Organic Chemistry
Pharmacy
Pyrimidines
Regioselectivity
Substrates
Synthesis
Type 2 diabetes
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Summary:Efficient and regioselective on-water synthesis of variously substituted 5-amino-4,7-dihydropyrazolo[1,5- a ]pyrimidine-6-carbonitriles and 5-amino-4,7-dihydro[1,2,4]triazolo[1,5- a ]pyrimidine-6-carbonitriles using 1,8-diazabicyclo[5.4.0]undec-7-ene as catalyst has been demonstrated. The reaction of 2-benzylidenemalononitriles and 3-aryl-1 H- pyrazol-5-amines or 1 H -1,2,4-triazol-5-amine allows to obtain the respective pyrazolo[1,5- a ]pyrimidines and [1,2,4]triazolo[1,5- a ]pyrimidines in high yields up to 93%. Main advantages of the developed synthetic protocol are application of water as environmentally friendly solvent, short reaction times, simple workup procedure that often does not require further purification of products, and broad substrate scope.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-019-02449-x