DFT Calculation, Hirshfeld Analysis and X-Ray Crystal Structure of Some Synthesized N-alkylated(S-alkylated)-[1,2,4]triazolo[1,5-a]quinazolines

被引：2
|
作者：
Abuelizz, Hatem A. [1 ]
Soliman, Saied M. [2 ]
Ghabbour, Hazem A. [3 ]
Marzouk, Mohamed [4 ]
Abdellatif, Mohamed M. [5 ]
Al-Salahi, Rashad [1 ]
机构：
[1] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[2] Alexandria Univ, Fac Sci, Dept Chem, Alexandria 21321, Egypt
[3] Mansoura Univ, Fac Pharm, Dept Med Chem, Mansoura 35516, Egypt
[4] Natl Res Ctr, Organ Chem Ind Div, Chem Tanning Mat & Leather Technol Dept, Cairo 12622, Egypt
[5] Tokyo Metropolitan Univ, Grad Sch Sci, Dept Chem, 1-1 Minami Osawa, Tokyo 1920397, Japan
来源：
CRYSTALS | 2021年 / 11卷 / 10期
关键词：
triazoloquinazoline; cyclocondensation; thionation; alkylation; X-ray; DFT; Hirshfeld analysis; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ENERGIES; SERIES;
D O I：
10.3390/cryst11101195
中图分类号：
O7 [晶体学];
学科分类号：
0702 ; 070205 ; 0703 ; 080501 ;
摘要：
The present work aimed to synthesize 2-methylthio-triazoloquinazoline derivatives and study their X-ray, NMR, DFT and Hirshfeld characteristics. The cyclocondensation of dimethyl-N-cyanodithiocarbonate with 2-hydrazinobenzoic acid hydrochloride resulted in an intermediate, 2-methylthio-[1,2,4]triazolo[1,5-a]quinazolin-5-one (A), which upon treatment with phosphorus pentasulfide, transformed into the 2-methylthio-[1,2,4]triazolo[1,5-a]quinazolin-5-thione (B). Reaction of 2-methylthio-triazoloquinazolines (A & B) with alkyl halides (allyl bromide and ethyl iodide) in basic medium afforded 4-allyl-2-methylthio-[1,2,4]triazolo[1,5-a]quinazolin-5-one (1; N-alkylated) and 5-ethylthio-2-methylthio-[1,2,4]triazolo[1,5-a]quinazoline (2; S-alkylated), respectively. Their molecular and supramolecular structures were presented. Unambiguously, the molecular structures of 1 and 2 were confirmed via NMR and single-crystal X-ray diffraction. The resulting findings confirmed the structures of 1 and 2 and determined their crystalized system (monoclinic system; P2(1)/n space group). Hirshfeld analysis of 1 revealed the importance of the significantly short O & BULL;& BULL;& BULL;H (6.7%), S & BULL;& BULL;& BULL;S (1.2%) and C & BULL;& BULL;& BULL;C (2.8%); however, the short H & BULL;& BULL;& BULL;H (42.6%), S & BULL;& BULL;& BULL;H (16.3%) and C & BULL;& BULL;& BULL;C (4.3%) were showed in 2 by intermolecular interactions in the molecular packing. The 1,2,4-triazoloquinzolines (1 & 2) were anticipated to be relatively polar compounds with net dipole moments of 2.9284 and 4.2127 Debye, respectively. The molecular electrostatic potential, atomic charge distribution maps and reactivity descriptors for 1 and 2 were also determined. The calculated nuclear magnetic resonance spectra of the targets 1 and 2 were well correlated with the experimental data.</p>
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页数：14
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