Synthesis of some new heterocycles containing quinazoline moiety View Full Text


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Article Info

DATE

2017-10

AUTHORS

F. Tajfirooz, A. Davoodnia, M. Pordel, M. Ebrahimi, S. A. Beyramabadi

ABSTRACT

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. More... »

PAGES

2429-2435

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070363217100255

DOI

http://dx.doi.org/10.1134/s1070363217100255

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1092632287


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