the reactivity of 2-ethoxy-4-chloroquinazoline and its use in synthesis of novel quinazoline derivatives2-ethoxy-4-chloroquinazoline的反应性和使用新型喹唑啉衍生物的合成.pdfVIP

Hindawi Publishing Corporation Organic Chemistry International Volume 2011, Article ID 295491, 7 pages doi:10.1155/2011/295491 Research Article The Reactivity of 2-Ethoxy-4-Chloroquinazoline and Its Use in Synthesis of Novel Quinazoline Derivatives M. A. El-Hashash,1 K. M. Darwish,2 S. A. Rizk,1 and F. A. El-Bassiouny1 1 Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt 2 Chemistry Department, Science Faculty, Garyounis University, Benghazi, Libya Correspondence should be addressed to K. M. Darwish, kdarwish1962@ 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. 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)thiosemicarba- zide 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. 1. Introduction