Synthesis of polyfunctionally substituted heteroaromatic compounds via benzotriazolyl chalcones with antimicrobial and antifungal activities

Abstract

The utility of both 3‐(1‐benzotriazolyl) chalcone derivatives 3a‐c and 2‐(1‐benzotriazolyl)‐1,4‐pentadien‐3‐one (18) in the synthesis of some new 2‐(1H)‐pyridone, pyridine, pyrazole and isoxazole derivatives is reported. Antimicrobial and antifungal screening of some selected examples from the synthesized products were carried out. The structure of the newly synthesized compounds was elucidated by elemental analysis, ir, 1H and 13C nmr investigations.

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

“…Malononitrile in the presence of piperidine converted the chalcones 262 into the corresponding 2-pyridinones 263 through similar intermediates depicted above (Scheme 99) [125].…”

“…The formation of 155 is assumed to proceed via the condensation of hydrazine with the carbonyl group in chalcone 154 and subsequent cyclization to pyrazole 155 (Scheme 54) [125].…”

“…The formation of 157 is assumed to proceed via initial addition of hydrazine to the carbonyl group and the resulting product then cyclized to pyrazole (Scheme 55) [125]. The α-benzotriazolyl-α,β-unsaturated ketones 159 were generated stereoselectively from benzotriazolylacetophenone 158 [123] and the corresponding aldehyde using piperidines as a base.…”

Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN

“…Isoxazolines and pyrazolines are interesting five-membered heterocyclic compounds because of their biological and pharmacological importance, for example as anticancer [1], anti-viral [2], anti-inflammatory [3], anti-diabetic [4], anti-bacterial [5], antimicrobial, and antifungal agents [6]. Several isoxazoles and pyrazoles have agrochemical herbicidal and soil fungicidal activity and act as pesticides and insecticides [7,8].…”

The Reactivity of <i>Gem</i> Cyanoester Ketene Dithiolates towards the Development of Potent Antioxidant Heterocycles

“…3) In addition pyrazoles and isoxazoles are present in leading pharmaceuticals viz., Celebrex, Viagra, Valdecoxib. 4,5) Pyrimidine derivatives have been very well known in medicinal chemistry for their therapeutic applications.…”