Synthesis and Spectral Characterization of Some Novel Thiazolyl-Pyrazoline Derivatives Containing 1,2,3-Triazole Moiety

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 186; no. 2; pp. 263 - 270
• Main Authors: Shi, Hai, Liu, Fang-Ming, Shen, Song-Wei
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis 01.02.2011; Taylor & Francis Ltd
• Subjects: 1,2,3-triazole; Aromatic compounds; Carbothioamide; Chemical analysis; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; NMR; Nuclear magnetic resonance; Physical Sciences; pyrazoline; Science & Technology; thiazole; Triazoles; 1,3-DIPOLAR CYCLOADDITION REACTION; ANTIDEPRESSANT; Carbothioamide; 2-PHENYL-1,2,3-TRIAZOLE; thiazole; ANTIBACTERIAL; AGENTS; pyrazoline; INHIBITORS; 1,2,3-triazole
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2010.494647

A series of novel 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-(4-aryl-2-thiazoyl)-pyrazolines 6a-6r were synthesized using 2-aryl-4-formyl-1,2,3-triazoles 1a,b as the starting materials. Thus, reacting 1a,b with 1-arylethanones 2a-2c gave 1-aryl-3-(2-aryl-1,2,3-triazol-4-yl)-2-propen-1-ones 3a-3f. The reaction of the latter with thiosemicarbazide afforded 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-thiocarbamoyl-pyrazolines 4a-4f, which condensed with 2-bromo-1-arylethanones 5a-5c to afford the target compounds 6a-6r. The chemical structures of the compounds were verified by means of their IR, 1 H NMR, ESI-MS spectroscopic data, and elemental analysis. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT