Synthesis, Characterization and Density Functional Theory Study of Di-Acylation
of N-Aminoquinazolin-4(3H)-one Derivatives
Al-Sehemi, AG [ 1,2 ]; Al-Amri, RSAAA [ 1 ]; Irfan, A [ 1 ]
JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN
Volume: 35, Issue: 3, Pages: 815-822, Published: JUN 2013
Publisher CHEM SOC PAKISTAN, HEJ RES INST CHEM UNIV KARACHI, 75270
KARACHI, PAKISTAN
ISSN: 0253-5106
Abstract
We have synthesized N-Acetyl-N-(2-ethyl-4-oxo-4H-quinazolin-3-yl)-acetamide,
N-Acetyl-N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)-acetamide,
N-Acetyl-N-(2-ethyl-4-oxo-4H-quinazolin-3-yl)-benzamide and
N-Acetyl-N-(2-benzhydryl-4-oxo-4H-quinazolin-3-yl)-acetamide then characterized by IR
and NMR techniques. The molecular geometries and vibrational frequencies of DAQ
derivatives at the ground state have been calculated using density functional theory at
B3LYP/6-31G* level of theory. The optimized bond lengths and bond angles showed
better agreement with the experimental values. The calculated HOMO and LUMO
energies also confirm that charge transfer occurs within the molecule. According to the
DFT calculation, the quinazolinone and imide planes, linked by the N-N bond, are as
expected approximately orthogonal and the imide carbonyl groups are present as
mixtures of exo-endo and endo-exo conformations. The N-N rotation barrier has been
explained on the basis of DFT theory.
Keywords
Author Keywords:Di-Acylation of N-Aminoquinazolin-4(3H)-one derivative;
Microwave-assisted reactions; Density functional theory; Geometrical parameters;
Infrared; Rotation barrier
KeyWords Plus:ORGANIC-SYNTHESIS; ELECTRON-DIFFRACTION;
MOLECULAR-STRUCTURE; MICROWAVE-OVENS; SUBSTITUENTS; BARRIERS;
ROTATION; AGENTS; 2,4-DIAMINOQUINAZOLINES; ANTIBACTERIAL
Author Information
Reprint Address: Al-Sehemi, AG E-mail Addresses:agmasq@gmail.com;
irfaahmad@gmail.com
King Khalid Univ, Fac Sci, Dept Chem, POB 9004, Abha 61413, Saudi Arabia.
Organization-Enhanced Name(s)
King Khalid University
Addresses:
[ 1 ] King Khalid Univ, Fac Sci, Dept Chem, Abha 61413, Saudi Arabia
Organization-Enhanced Name(s)
King Khalid University
[ 2 ] King Khalid Univ, Fac Sci, Unit Sci & Technol, Abha 61413, Saudi Arabia