Three‐Component Uncatalyzed Eco‐Friendly Reactions for One‐Pot Synthesis of 4,7‐Dihydro[1,2,4]triazolo[1,5‐a]pyrimidine Derivatives

Abstract

A three‐component system of one‐pot synthesis of [1,2,4]triazolo[1,5‐a]pyrimidine derivatives using condensation of 1,3‐dicarbonyl compounds, aldehydes, and 5‐amino[1,2,4]triazole in ethanol without any catalyst was reported in high yields via simple, efficient, and environmentally friendly process. The method reported herein considered a green process; this method has significant advantages of simple workup procedure, excellent yield, minimal environmental pollution, and short reaction time over classical reported methods.

Three Component One-Pot Synthesis and Antiproliferative Activity of New [1,2,4]Triazolo[4,3-a]pyrimidines

“…Based on the above results and drawing inspiration from the results reported in the literature [37,38], we hypothesized that the mechanism of the three-component one-pot reaction could be as follows (Scheme 2).…”

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

“…The heterocyclization was regio‐ and position‐selective and gave only one type of final compounds. A similar reaction involving acetylacetone and different aldehydes (alkyl, aryl, hetaryl) was published in work [158] . The three‐component treatment was also carried out in ethanol without a catalyst.…”

“…A similar reaction involving acetylacetone and different aldehydes (alkyl, aryl, hetaryl) was published in work. [158] The three-component treatment was also carried out in ethanol without a catalyst. The authors discussed the plausible mechanism of condensation via the formation of the arylidene derivative of acetylacetone and the subsequent nucleophilic attack of the 2-N atom of the aminotriazole on its cinnamoyl fragment, however, no evidence for this mechanism was provided in the article.…”

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

“…The conclusions of Sedash et al about preferential formation of compounds with the structure of type A in the multicomponent reactions involving 3-amino-1,2,4-triazole were confirmed by the subsequent publications of other authors: 4,7-dihydroazolo[1,5- a ]pyrimidines were synthesized from 3-amino-1,2,4-triazole or 5-aminotetrazole, aromatic aldehydes and acetone, α-acetyl-butyrolactone, acetylacetone or acetoacetic acid derivatives (Ryabukhin et al, 2011 ; Gein et al, 2012 , 2014 ; Kumari et al, 2012 ; Li et al, 2012 ; Liu et al, 2012b ; Rajua et al, 2012 ; Ghorbani-Vaghei et al, 2013 ; El Rady, 2014 ; Haleel et al, 2014 ; Bhatt et al, 2015 ; Adrom et al, 2016 ; Komykhov et al, 2016 , 2017 ; Gümüş et al, 2017b ; Kour et al, 2017 ; Maleki et al, 2017 ).…”