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SYNTHESIS OF 4,7-DIHYDRO[1,2,4]TRIAZOLO[1,5-a]PYRIMIDINE-6-SULFONAMIDE DERIVATIVES

Максим А. Колосов, Муатаз Д. К. Ал-Огаили, Олеся Г. Кулык, Валерий Д. Орлов
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Abstract


A three-component condensation of 1-(1-piperidinylsulfonyl)acetones, aromatic aldehydes, and 3-amino-1,2,4-triazole in DMF leads to the formation of 5-alkyl-6-(1-piperidinylsulfonyl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine derivatives. If 4-nitrobenzaldehyde is employed, 5-methyl-7-(4-nitrophenyl)[1,2,4]triazolo[1,5-a]pyrimidine is the single isolated reaction product. The starting 1-(1-piperidinylsulfonyl)acetones were obtained from 1-(methylsulfonyl)piperidine in sequential metalation with n-butyllithium, reaction with aliphatic aldehydes, and oxidation of the obtained sulfoalcohols.

How to Cite
Kolosov, M. A.; Al-Ogaili, M. J. K.; Kulyk, O. G.; Orlov, V. D. Chem. Heterocycl. Compd. 2015, 51, 691. [Khim. Geterotsikl. Soedin. 2015, 51, 691.]

For this article in the English edition see DOI 10.1007/s10593-015-1759-5


Keywords


4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-sulfonamides; 1-(1-piperidinylsulfonyl)acetones; alkylation; metalation; three-component condensation

Full Text: PDF (Russian) Supplementary File(s): Supporting information (14MB)


 

 

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