Synthesis of new thiazine and thiazole derivatives via cyclization reactions; investigating their electronic properties and determination of antioxidant properties


Ergan E., Tozlu D.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.59, no.9, pp.1651-1659, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 9
  • Publication Date: 2022
  • Doi Number: 10.1002/jhet.4498
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), Chemical Abstracts Core, Chimica, EMBASE
  • Page Numbers: pp.1651-1659
  • Van Yüzüncü Yıl University Affiliated: Yes

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, H-1, and C-13.