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ALKYLATION OF 6-C(O)R-7-ARYL-5-METHYL-4,7-DIHYDRO[1,2,4]TRIAZOLO[1,5-a]PYRIMIDINES

Максим А. Колосов, Елена Г. Швец, Олеся Г. Кулык, Валерий Д. Орлов
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Abstract


Alkylation of 6-C(O)R-7-aryl-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines with methyl iodide or ethyl bromide in either saturated aqueous KОН–MeCN or NaH–DMF led to the formation of N4-alkyl derivatives in good yields (60–98%). Reactivity of the acetyl group of N4-alkyl derivatives towards aromatic aldehydes under the conditions of the Claisen–Schmidt reaction was significantly higher than in 4-unsubstituted compounds. The starting 6-C(O)R-7-aryl-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines were synthesized via a three-component condensation of an aromatic aldehyde, 3-amino-1,2,4-triazole, and a dicarbonyl compound (2,4pentanedione or ethyl acetoacetate) in DMF.

How to Cite
Kolosov, M. A.; Shvets, E. H.; Kulyk, O. G.; Orlov, V. D. Chem. Heterocycl. Compd. 2015, 51, 1052. [Khim. Geterotsikl. Soedin. 2015, 51, 1052.]

For this article in the English edition see DOI 10.1007/s10593-016-1818-6

 


Keywords


4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines; alkylation; Claisen–Schmidt reaction; Biginelli reaction; three-component condensation

Full Text: PDF (Russian) Supplementary File(s): (7MB) Supplementary materials (8MB)


 

 

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