Synthesis,Structural, and Theoretical Studies of Quinazoline-2,4-dione Derivatives |
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Authors: | Hamdy S El-Sheshtawy Aboubakr Haredi Abdelmonsef Sayed Moustafa Abboudy Ahmed Mohamed Mosallem Younes Mohamed Mobark Taha Mamdouh Adly Hassan |
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Affiliation: | 1. Chemistry Department, Faculty of Science, Kafrelsheikh University, Kafr ElSheikh, Egypt;2. Chemistry Department, Faculty of Science, South Valley University, Qena, Egypt;3. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Sinai University, Arish, Egypt |
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Abstract: | New quinazolin-2,4-dione derivatives have been synthesized and fully characterized. The new derivatives were synthesized using 3-(2-imino-4-oxo-3H,4H,5H-thiazolidin-3-yl)-1H-quinazolin-2,4-dione by nucleophilic addition mechanism. DFT calculations using B3LYP/6–311++G(d,p) level of the theory were used to investigate the molecular structures and the relative stabilities of the anticipated isomers (E and Z). Both experimental and theoretical calculations confirmed the higher stability of the Z-isomers compared to the E-isomers. The former is stabilized by two intramolecular hydrogen bonds compared to only one in the latter isomer. The frontier orbital calculations (HOMO and LUMO), and the energy gap confirmed the stability of the molecules. |
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Keywords: | 3-amino-1H-quinazolin-2 4-dione arylidines isomeric forms quantum chemical calculations |
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