Synthesis of some new heterocycles containing quinazoline moiety
- Autores: Tajfirooz F.1, Davoodnia A.1, Pordel M.1, Ebrahimi M.1, Beyramabadi S.1
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Afiliações:
- Department of Chemistry, Mashhad Branch
- Edição: Volume 87, Nº 10 (2017)
- Páginas: 2429-2435
- Seção: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/221470
- DOI: https://doi.org/10.1134/S1070363217100255
- ID: 221470
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Resumo
The presented herein synthesis of new quinazolines and quinazolino[3,4-a]quinazolines started from 2-amino-N-alkylbenzamides. Reaction of 2-amino-N-alkylbenzamides with 2-nitrobenzaldehyde followed by reduction using Zn afforded the corresponding 3-alkyl-2-(2-aminophenyl)-2,3-dihydroquinazolin-4(1H)-ones. Cyclization of the later compounds with carbon disulfide followed by methyl iodide, triethyl orthoformate or dimethyl acetylenedicarboxylate (DMAD) gave new quinazolino[3,4-a]quinazoline derivatives that were characterized on the basis of FT-IR, 1H, and 13C NMR spectra, and microanalytical data. In the case of reaction with DMAD, 2D nuclear Overhauser effect (2D-NOESY) spectrum together with comparison of the experimental and calculated chemical shifts at the B3LYP/6-311+G(d,p) level of theory were also used to identify the correct stereoisomer.
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Sobre autores
F. Tajfirooz
Department of Chemistry, Mashhad Branch
Email: adavoodnia@mshdiau.ac.ir
Irã, Mashhad, 9175687119
A. Davoodnia
Department of Chemistry, Mashhad Branch
Autor responsável pela correspondência
Email: adavoodnia@mshdiau.ac.ir
Irã, Mashhad, 9175687119
M. Pordel
Department of Chemistry, Mashhad Branch
Email: adavoodnia@mshdiau.ac.ir
Irã, Mashhad, 9175687119
M. Ebrahimi
Department of Chemistry, Mashhad Branch
Email: adavoodnia@mshdiau.ac.ir
Irã, Mashhad, 9175687119
S. Beyramabadi
Department of Chemistry, Mashhad Branch
Email: adavoodnia@mshdiau.ac.ir
Irã, Mashhad, 9175687119