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

Author:

El-Hashash M. A.1,Darwish K. M.2,Rizk S. A.1,El-Bassiouny F. A.1

Affiliation:

1. Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt

2. Chemistry Department, Science Faculty, Garyounis University, Benghazi, Libya

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.

Publisher

Hindawi Limited

Subject

General Earth and Planetary Sciences,General Engineering,General Environmental Science

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