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

Authors

  • Максим А. Колосов V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine
  • Муатаз Д. К. Ал-Огаили V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine
  • Олеся Г. Кулык V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine
  • Валерий Д. Орлов V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

DOI:

https://doi.org/10.1007/2511

Keywords:

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

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

Author Biographies

Максим А. Колосов, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

Максим Александрович Колосов

доцент, кафедра органической химии

Муатаз Д. К. Ал-Огаили, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

Муатаз Д. К. Ал-Огаили

Олеся Г. Кулык, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

Олеся Г. Кулык

Валерий Д. Орлов, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

Валерий Д. Орлов

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Published

2015-07-14

Issue

Vol. 51 No. 7 (2015)

Section

Letters to the Editor