Table of Contents
Organic Chemistry International
Volume 2011, Article ID 295491, 7 pages
http://dx.doi.org/10.1155/2011/295491
Research Article

The Reactivity of 2-Ethoxy-4-Chloroquinazoline and Its Use in Synthesis of Novel Quinazoline Derivatives

1Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt
2Chemistry Department, Science Faculty, Garyounis University, Benghazi, Libya

Received 9 July 2011; Revised 16 September 2011; Accepted 21 September 2011

Academic Editor: Mahesh Lakshman

Copyright © 2011 M. A. El-Hashash et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The behavior of 2-ethoxy-4-chloroquinazoline 2 towards various nitrogen nucleophiles, namely: thiosemicarbazide, sodium azide, glucosamine, ethanol, and hydrazine hydrate has been discussed. Also, the behavior of 4-(2-ethoxyquinazolin-4-yl)thiosemicarbazide towards one-carbon, for example, ethyl chloroformate, and two-carbon donors, for example, ethyl chloroacetate and diethyl oxalate has been investigated. On the other hand, new 5-ethoxy-2-substituted[1,2,4]-triazolo-[1,5-c]quinazoline derivatives have been obtained by ring closure accompanied with Dimroth rearrangement through the interaction of compound 2 with hydrazides of acetic, benzoic, crotonic, cinnamic, 2-furoic, and phthalimidoacetic acids. Structures of the novel products were confirmed by elemental, IR, MS, and 1H-NMR spectral analyses.