| Abstract | Tiazol je peteročlani prsten koji sadrži atome dušika i sumpora na položajima 1 i 3. Tiazol je dobio značajnu pozornost u područjima organske i medicinske kemije zbog svojih izvanrednih bioloških i farmakoloških svojstava. Spojevi na bazi tiazola pokazaju širok spektar bioloških aktivnosti, uključujući antimikrobna, antitumorska, protuupalna i antioksidacijska djelovanja. Istraživanje derivata tiazola rezultiralo je razvojem brojnih komercijalno dostupnih lijekova koji sadrže tiazolski prstenasti sustav. Primjeri ovih lijekova uključuju ritonavir, sulfatiazol, bleomicin, pramipeksol, febuksostat, vitamin B 1 i mnoge druge. Ovi farmaceutski proizvodi ističu raznoliki terapijski potencijal spojeva na bazi tiazola. Glavni zadatak ovog rada bio je razviti praktičnu i učinkovitu metodu sinteze 1,3-tiazola in situ. Primarni cilj bio je otkriti nove sintetske puteve za dobivanje tiazola koristeći jednostavnije i dostupnije početne materijale. Ova metodologija je izvedena integracijom Hantzschove reakcije s mikrovalnim zračenjem. U početku su se koristili alkoholi koji su se pretvarali u α-halokarbonilne spojeve putem oksidacije i kloriranja. Za oksidaciju je korišten 2,2,6,6-tetrametilpiperidin-1-il-oksi radikal (TEMPO), dok je trikloroizocijanurna kiselina (TCCA) služila kao izvor klora. Nakon toga, proces Hantzschove sinteze je nastavljen, što je dovelo do formiranja 1,3-tiazola. Upotreba mikrovalnog zračenja rezultirala je bržom reakcijom, poboljšanim prinosima čistih produkata i pojednostavljenim postupcima obrade. Ovo istraživanje je pokazalo brojne prednosti mikrovalnog zračenja u odnosu na konvencionalne metode zagrijavanja. |
| Abstract (english) | Thiazole is a five-membered moiety composed of nitrogen and sulfur atoms at positions 1 and 3, respectively. It has received significant attention in the fields of organic and medicinal chemistry due to its remarkable biological and pharmacological properties. Thiazole- based compounds have demonstrated a wide range of biological activities, including antimicrobial, antitumor, anti-inflammatory, and antioxidant activities, among others. The extensive exploration of thiazole derivatives has resulted in the development of numerous commercially marketed drugs that contain the thiazole ring system. Examples of these drugs include ritonavir, sulfathiazole, bleomycin, pramipexole, febuxostat, vitamin B 1 and many more. These pharmaceuticals highlight the diverse therapeutic potential of thiazole-based compounds. The main objective of this study was to develop a convenient and efficient one-pot synthesis method for 1,3-thiazoles. The primary aim was to discover novel synthetic routes for obtaining thiazoles utilizing more simple and available starting materials. This methodology was achieved by integrating the Hantzsch reaction with microwave irradiation. Initially, alcohols were utilized and transformed into α-halocarbonyl compounds through oxidation and chlorination. For oxidation, 2,2,6,6-tetramethylpiperidin-1-yl oxyl radical (TEMPO) was employed as the oxidant, while trichloroisocyanuric acid (TCCA) served as a chlorine source. Subsequently, the Hantzsch synthetic process proceeded, leading to the formation of 1,3-thiazoles. The utilization of microwave irradiation resulted in accelerated reaction rates, improved yields of pure products, and simplified workup procedures. This study demonstrated the numerous advantages of microwave irradiation over conventional heating methods. |
