One-pot four-component synthesis of highly substituted [1,2,4]triazolo[1,5-a]pyrimidines

Abstract

A green one-pot four-component strategy has been developed for the synthesis of [1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide derivatives using an amine, 2,2,6-trimethyl-4H-1,3-dioxin-4-one, an aldehyde, and 3-amino-1,2,4-triazole in the presence of a catalytic amount of p-toluenesulfonic acid in water within 4-6 h.

Copper supported on MWCNT-guanidine acetic acid@Fe3O4: synthesis, characterization and application as a novel multi-task nanocatalyst for preparation of triazoles and bis(indolyl)methanes in water

“…It is well known that H 2 O is considered as a green solvent for various chemical and biological reactions, and by considering both economic and environmental aspects during the course of this research, towards the development of new routes to the synthesis of organic compounds using H 2 O as a green medium, [55][56][57][58] it was decided to used H 2 O as an environment friendly solvent. The results show that the click reaction was successfully carried out in H 2 O with good to excellent yield.…”

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

“…Different amines and aldehyhdes have been tested and the yields are high (Scheme 61). [71] N,7-diaryl-5-methyl-4,7-dihydro- [1,2,4]-triazolo[1,5-a]-pyrimidine-6-carboxamides 99 (90-95 %), under solvent-free conditions using maltose as a commercially available, cheap and eco-friendly catalyst, were prepared by Adrom et al [72] via one-pot, three-component reaction under stirring at 80 °C for the appropriate time (14-25 h) (Scheme 62).…”

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

“…The intermediate was then allowed to participate in the MCR with various aldehyde 4 and 3-amino-1,2,4-triazole 16 in the presence of a catalytic amount of p -toluenesulfonic acid (PTSA) in water for the synthesis of [1,2,4]triazolo[1,5- a ]pyrimidine-6-carboxamide derivatives 59 ( Scheme 19 ). 60 …”