ACETIC ALDEHYDE IN MULTICOMPONENT SYNTHESIS OF AZOLOPYRIMIDINE DERIVATIVES IN WATER

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.

Author Biographies

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

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

Kharkiv Scientific Expertize-Criminalistics Department, Ministry of Internal Affairs of Ukraine

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

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

V. N. Karazin Kharkiv National University

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

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

V. N. Karazin Kharkiv National University

Vladimir I. Musatov, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

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

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

V. N. Karazin Kharkiv National University

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

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

V. N. Karazin Kharkiv National University

Published

2019-05-22