ACETIC ALDEHYDE IN MULTICOMPONENT SYNTHESIS OF AZOLOPYRIMIDINE DERIVATIVES IN WATER

Irina G. Tkachenko; Sergey A. Komykhov; Eugene S. Gladkov; Vladimir I. Musatov; Valentyn A. Chebanov; Sergey M. Desenko

doi:10.1007/5014

Authors

Irina G. Tkachenko State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072 V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022 Kharkiv Forensic Science Center, Ministry of Internal Affairs of Ukraine, 32 Kovtuna St., Kharkiv 61036
Sergey A. Komykhov State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072 V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022
Eugene S. Gladkov State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072 V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022
Vladimir I. Musatov State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072
Valentyn A. Chebanov State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072 V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022
Sergey M. Desenko State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072 V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022

DOI:

https://doi.org/10.1007/5014

Keywords:

acetaldehyde, 1, 3-dicarbonyl compound, 2, 3-triazole, 4-triazole, triazolo[1, 5-a]pyrimidine, microwave-assisted synthesis, multicomponent reaction

Abstract

Three-component reaction of 3-amino-1H-1,2,4-triazole or 5-amino-2H-1,2,3-triazole derivatives, acetaldehyde, and 1,3-dicarbonyl compounds (acetylacetone or β-keto esters) in water under microwave irradiation leads to regioselective formation of 4,7-dihydro[1,2,4]triazolo- and 4,7-dihydro[1,2,3]triazolo[1,5-a]pyrimidines. Using ethyl 4,4,4-trifluoro-3-oxobutanoate as 1,3-dicarbonyl compound under the same conditions allows to obtain the corresponding 5-hydroxy-4,5,6,7-tetrahydro derivatives, which fail to dehydrate in the reaction medium.