Synthesis of 5-(Thiazol-5-yl)-4,5-dihydroisoxazoles from 3-Chloropentane-2,4-dione

Abstract

Condensation of 3-chloropentane-2,4-dione with thioamides gives 1-(thiazol-5-yl)ethanones and subsequent Wittig olefination, followed by nitrile oxide 1,3-dipolar cycloaddition to the resulting prop-1-en-2-yl moiety, delivers racemic 5-(thiazol-5-yl)-4,5-dihydroisoxazoles. When this thiazole and isoxazoline diheterocyclic scaffold has a carboethoxy substituent at C2 of the thiazole ring, aminolysis provides for effective diversification. A 50-member library of various 5-(thiazol-5-yl)-4,5-dihydroisoxazoles is reported.

Synthesis of new series of thiazol‐(2(3H)‐ylideneamino)benzenesulfonamide derivatives as carbonic anhydrase inhibitors

“…[1] Especially, heterocyclic compounds containing thiazole ring have an important role in medical chemistry because of their biological properties starting from antimicrobial to antitumour activity. [2][3][4][5] Also, many currently notable drugs contain sulfonamides because of the high level of similarity to para-aminobenzoic acid (PABA), which is the main metabolite for many microorganisms and which is found in the structure of the purines, in terms of chemical structure. Due to this similarity, sulfoamides inhibit nucleic acid synthesis by substituting PABA in bacteria and show bacteriostatic effect.…”

Synthesis of some novel pyrazoline‐thiazole hybrids and their antimicrobial activities

“…Recently, some thiazoles were discovered as new inhibitors of bacterial DNA gyrase B. [32][33][34][35][36] Thiazoles have been also used in the treatment of allergies. [37] In the light of previous data and in continuation of our interest in the synthesis of new biologically active heterocycles, [38][39][40][41][42][43] in this study, we aimed to synthesize certain pyrazoline derivatives incorporating thiazole moiety to evaluate their antimicrobial potency.…”

“…Moreover, thiazole derivatives showed a broad spectrum of biological activity, they have been reported as anticonvulsant, antibacterial, antifungal, antiviral, and anticancer agents. Recently, some thiazoles were discovered as new inhibitors of bacterial DNA gyrase B . Thiazoles have been also used in the treatment of allergies .…”

Synthesis, Characterization, and Antifungal Activity Evaluation of Some Novel Arylazothiazoles

“…One of the most important heterocyclic compounds is thiazole ring because of the wide range of biological activities . Several marketing drugs for several diseases contain thiazole moiety such as sulfathiazole (antimicrobial drug), thiabenzadole (antifungal drug), ritonavir (antiretroviral), cefdinir (bacteriocidal antibiotic of the cephalosporin class of antibiotics), talipexole (treatment for Parkinson's disease), epothilones (cancer drugs), and simeprevir (a drug for the treatment and cure of hepatitis C) (Fig.…”