Naslov
Microwave-assisted one-pot synthesis of 1,3-thiazoles starting from primary alcohols

Autori
Šegedin, Adriana

Vrsta, podvrsta i kategorija rada
Ocjenski radovi, diplomski rad, diplomski

Fakultet
Kemijsko-tehnološki fakultet

Mjesto
Split

Datum
29.06

Godina
2023

Stranica
67

Mentor
Blažević, Ivica ; Guerra Martínez, Francisco

Ključne riječi
thiazole ; biological activity ; Hantzsch reaction ; microwave irradiation

Sažetak
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 B1 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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