In this study, 4,7-dihydrotetrazolo[1, 5-a]pyrimidine derivatives (1-5) were prepared via Multicomponent Cyclocondensation Reactions (MCRs). All structures were determined by using FT-IR, 1 H/ 13 C NMR and elemental analyses. The compounds were investigated as corrosion inhibitors using density functional theory (DFT) at the level of B3LYP/6-31G (d, p). According to the calculations, compound 1 appears to be a good inhibitor for corrosion. In addition, the electrochemical properties of the novel systems were investigated by CV.
In this research, 5‐benzoyl‐6‐phenyl‐4‐(4‐trifluoromethylphenyl)‐2‐{oxo and thioxo}‐3,4‐dihydro‐1H‐pyrimidines (1, 2) were synthesized by using multicomponent cyclocondensation reaction under microwave irradiation and classical heating. Compounds 3, 4, 6, 7, and 8 obtained reactions of 5‐benzoyl‐6‐phenyl‐4‐(4‐trifluoromethylphenyl)‐2‐thioxo‐3,4‐dihydro‐1H‐pyrimidine (1) and acetic anhydride, diethyl 2‐bromomalonate, bromoacetic acid, 3‐bromopropionic acid, methyl iodide, respectively. Compound 4 was both acetylated and hydrolyzed in acetic acid to give compound 5. The structures of all compounds were determined by using spectroscopic techniques like FT‐IR, 1H/13C NMR, and elemental analyses, and the structures of compounds 1 and 3 were analyzed by X‐ray crystal analysis. In addition, the quantum chemical parameters and full geometry optimizations for all compounds were computed using density functional theory based on B3LYP and the 6‐31G (d, p) basis set.
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.
In this work, we wanted to define a general and comprehensive strategy for
the synthesis of tetrazolo[1,5-a]pyrimidine derivatives. For this purpose,
we obtained new tetrazolo[1,5-a]pyrimidine molecules via the
mercury-promoted desulfurization reaction, including hydrolysis,
cyclizations, and eliminations. All of the molecules were characterized by
FT-IR, 1H NMR, 13C NMR, and elemental analysis. On the other hand, the
potentials of compounds as corrosion inhibitors were calculated at B3LYP /
6-31G (d, p) level via density functional theory (DFT).
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