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A Green Protocol for Simple One‐pot Synthesis of New Pyrimidine Derivatives Both Microwave Irradiation and Conventional Heating: Reactions, Characterization, and Theoretical Calculations
Author(s) -
Akbas Esvet,
Ruzgar Adem,
Sahin Ertan,
Ergan Erdem
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3483
Subject(s) - chemistry , acetic anhydride , pyrimidine , acetic acid , methyl iodide , elemental analysis , microwave irradiation , proton nmr , hydrolysis , iodide , organic chemistry , medicinal chemistry , nuclear chemistry , computational chemistry , catalysis , stereochemistry
In this research, 5‐benzoyl‐6‐phenyl‐4‐(4‐trifluoromethylphenyl)‐2‐{oxo and thioxo}‐3,4‐dihydro‐1 H ‐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‐1 H ‐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, 1 H/ 13 C 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.