Open Access Open Access  Restricted Access Subscription Access

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
Cover Image

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.


Keywords


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

Full Text: PDF Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv