Synthesis of new thiazine and thiazole derivatives via cyclization reactions; investigating their electronic properties and determination of antioxidant properties. (7th May 2022)

• Record Type: Journal Article
• Authors: Ergan, Erdem; Tozlu, Deniz
• Is Part Of: Journal of heterocyclic chemistry. Volume 59:Number 9(2022)
• Page Start: 1651
• Page End: 1659
• Publication Date: 2022-05-07
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.4498
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract: (4‐[2, 4‐dimethoxyphenyl]‐6‐phenyl‐2‐thioxo‐1, 2, 3, 4‐tetrahydropyrimidin‐5‐yl)(phenyl) methanone (1 ) have been prepared by Biginelli three‐component cyclocondensation reaction of catalyzed with p‐toluene sulfonic acid in ethanol. Pyrimido[2, 1‐ b ]thiazine (2 ) and thiazolo[3, 2‐ a ]pyrimidine (3 ) derivatives were obtained by a simple one‐pot condensation reaction of starting compound 1 and 3‐bromopropionic acid, bromoacetic acid and, respectively. By performing the reactions of compound 3 with heteroaromatic and aromatic aldehydes, arylidine‐bicyclic thiazolo pyrimidine compounds (4–9 ) were synthesized. Theoretical calculations and molecular electrostatic potential maps of all synthesized compounds were performed using the Gaussian software package Density Functional Theory (DFT/6‐31G: B3LYP). In addition, studies were carried out to determine the antioxidant properties of all the compounds obtained by the DPPH method, and compound 1 was found to be the most effective compound. The structures of the newly synthesized compounds were analyzed using spectroscopic methods such as IR, 1 H, and 13 C. Abstract :