One‐Pot Synthesis of (1,2,3‐Triazolyl)methyl 3,4‐Dihydro‐2‐oxo‐1H‐pyrimidine‐5‐carboxylates as Potentially Active Antimicrobial Agents

Abstract

A simple and efficient one‐pot four‐component procedure has been developed for the synthesis of a wide range of compounds containing the (triazolyl)methyl oxo‐pyrimidine‐carboxylate system from propargyl β‐keto esters, various azides, aldehydes, and urea in the presence of catalytic amounts of (AcO)2Cu/sodium ascorbate in AcOH. The method worked well with different aryl and heteroaryl aldehydes, and for a variety of substituents in the triazolyl part of the molecule. The antimicrobial activities of the products were evaluated against two Gram‐positive and Gram‐negative bacteria, and one fungus. Compound 5j was active against Staphylococcus aureus and Candida albicans.

β‐Ketoesters: An Overview and It's Applications via Transesterification

“…1,2,3-Triazolesareimportant category of N-heterocyclic compounds, having immense promise since few decades in medicinal chemistry [199] predominantly as antimicrobial, [200] anticancer, [201] anti-HIV, [202] antitubercular [203] and antifungal agents. [204] Conversely, this particular class of scaffolds has also found significance in materials and surface science, [205] objective oriented synthesis, [206] combinatorial chemistry, [207] bioconjugation [208] and medicinal chemistry.…”

Design, synthesis, and characterization of (1-(4-aryl)-1<em>H</em>-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against <em>Mycobacterium tuberculosis</em>

“…Natural and synthetic dihydropyrimidine derivatives have a wide range of pharmacological actions, such as anticancer, 1 antiviral, 2 , 3 antihypertensive, 4 calcium channel blocking, 5 antitubercular, 6 antimicrobial, 7 , 8 anti-inflammatory, 9 , 10 and larvicidal and insecticide actions. 11 , 12 1,2,3-Triazoles, as a vital class of N -heterocyclic compounds, due to their unique chemical and structural properties, have received a great deal of attention over the past few decades and found broad application in medicinal chemistry 13 and particularly as anticancer, 14 antimicrobial, 15 antitubercular, 16 anti-HIV, 17 and antifungal agents. 18 On the other hand, this special class of scaffolds has also found relevance in objective oriented synthesis, 19 bioconjugation, 20 materials and surface science, 21 combinatorial chemistry, 22 and medicinal chemistry.…”