Selectivity in domino reaction of ortho-carbonyl azides with malononitrile dimer leading to [1,2,3]triazolo[1,5-a]pyrimidines

The selectivity of the domino reaction of the (het)aryl azides, containing the carbonyl center in the ortho position to the azido group, with malonodinitrile dimer was studied. It has been shown that in the case of aromatic azides bearing a carboxy or nitrile function in the ortho position, the reac...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-02, Vol.54 (2), p.209-212
Main Authors: Pokhodylo, Nazariy T., Shyyka, Olga Ya, Tupychak, Mykola A., Obushak, Mykola D.
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbonyls
Cascade chemical reactions
Chemistry
Chemistry and Materials Science
Fish
Malononitrile
Nitriles
Organic Chemistry
PCB
Pharmacy
Polychlorinated biphenyls
Pyridine
Pyrimidines
Selectivity
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Summary:The selectivity of the domino reaction of the (het)aryl azides, containing the carbonyl center in the ortho position to the azido group, with malonodinitrile dimer was studied. It has been shown that in the case of aromatic azides bearing a carboxy or nitrile function in the ortho position, the reaction occurred with the formation of exclusively [1,2,3]triazolo[1,5- a ]pyrimidine instead of [1,2,3]triazolo[4,5- b ]pyridine system. Thus, new [1,2,3]triazolo[1,5- a ]quinazolines, thieno[2,3- e ][1,2,3]triazolo[1,5- a ]pyrimidine, and thieno[3,2- e ][1,2,3]triazolo[1,5- a ]-pyrimidines, having polyfunctional 1-amino-2,2-dicyanovinyl fragment, were prepared in short time in high yields.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-018-2256-4