Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Abstract

The compound, diethyl 1-((4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate 2, was synthesized in high yield, through 1,3-dipolar cycloaddition reaction of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and diethyl but-2-ynedioate in the absence of a solvent. The structure of the synthesized compound was established on the basis of NMR spectroscopy ( 1 H, 13 C), X-ray crystallography, and MS data. The prepared compound was also tested in vitro for its antibacterial activity against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The calculation of MBC/MIC ratio showed that this triazole derivative 2 had a bactericidal effect on the two strains tested.

Diethyl 1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazole-4,5-dicarboxylate

“…The approach for the synthesis of 1,2,3-triazole-substituted compounds involves transformation of the azide function in a 1,3-dipolar cycloaddition reaction with acetylene derivatives. In this context, the title compound was obtained with good yield (Boukhssas et al, 2017).…”

“…The approach for the synthesis of 1,2,3-triazole-substituted compounds involves transformation of the azide function in a 1,3-dipolar cycloaddition reaction with acetylene derivatives. In this context, the title compound was obtained with good yield (Boukhssas et al, 2017).In the title compound, Fig. 1, the central triazole ring is planar (r.m.s deviation = 0.0054 (13) Å ) and makes dihedral angles of 56.15 (8) and 43.25 (9) with the oxazol and benzene rings, respectively.…”

Synthesis, characterization & in vitro antimicrobial‐antioxidant studies of novel N,1‐diphenyl‐4,5‐dihydro‐1H‐1,2,4‐triazol‐3‐amine derivatives

“…Thus, syntheses of triazole‐containing heterocycles have attracted the attentions of organic chemists in the past decades. Triazoles are the nontoxic, mostly water soluble and highly stable compounds because they could actively participate in molecular interactions by hydrogen bonding, which implies their ability to bind with different biological targets . Among the triterpenes, the antimicrobial effects have been enhanced by the introduction of triazole ring .…”

4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole

“…In the continuation of our research concerning heterocyclic amino acids and their precursors [10][11][12][13][14], we described in this short note our results concerning the synthesis of a new pyrazole compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole, an oxazolinic precursor of heterocyclic amino acids via nucleophilic substitution reaction of the (4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl-4-methylbenzenesulfonate and the 3,5-dimethyl-1H-pyrazole. The title compound was characterized by spectroscopic techniques, such as 1D and 2D NMR spectroscopy, mass spectrometry (MS) and elemental analysis.…”