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. 1. Introduction Quinazolines are a big family of heterocyclic compounds, which have shown broad variety of biological activity profiles [1, 2], for example, analgesic, narcotic, diuretic, antihypertensive, antimalarial, sedative, hypoglycaemic, antibiotic, antitumoral, and many others. It has been found [3] that the biological activity strongly depends on the type and place of the substituents in their molecules. Out of the wide substitution patterns known, 4-aminoquinazolines are useful as fungicides [4, 5], anti-inflammatory [6, 7], anticancer [8, 9], antimicrobial, and antihypertensive agents [10, 11]. Some 4-anilinoquinazolines have been found to be potential and highly selective inhibitors of human immunoglobulin E [12] and epidermal growth factor receptor tyrosine kinase [13] which regulates the cell growth and proliferation, so they can work as potent antiallergic or anticancer agents, respectively. Among the broad synthetic pathways for aminoquinazoline preparation [14, 15] the substitution of chlorine atom in 4-chloroquinazolines by amines is the shortest and cheapest one. On the other hand, it is well known that heterocycle-bearing N-glycosides play a significant role as inhibitors, for example, the tetrazole-bearing N-glycosides used as SGLT2 inhibitors [16] where their hypoglycemic activity is tested in vivo by mice oral glucose tolerance test (OGTT). In the current paper we report the synthesis of 4-aminoquinazoline-bearing N-glycosides in a similar way, with exception of the endocyclic 2° nitrogen atom attached to the glucose moiety. 2. Results and Discussion In many syntheses of quinazoline derivatives the 4-chloroquinazoline exhibits a very important key intermediate due to its reactivity towards many types of nucleophiles, especially the
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