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Reactions of 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines with α,β-unsaturated carbonyl compounds

✍ Scribed by Victoria V. Lipson; Irina V. Ignatenko; Sergey M. Desenko; Svetlana V. Shishkina; Oleg V. Shishkin; Sergey A. Komykhov; Natalya V. Logvinenko; Valery D. Orlov; Herbert Meier

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
57 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 5,7‐diphenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine (1) with α,β‐unsaturated carbonyl compounds 2a‐f led to the formation of the alkylated heterocycles 3a‐f (Figure 1). However, the reaction of 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine (5) with 2a‐c yielded under the same conditions the triazolo[5,1‐b]quinazolines 6a‐c (Figure 3). In this case, the alkylation is followed by a cyclocondensation. The structure elucidation of the products is based on ir, ms, ^1^H and ^13^C nmr measurements and on an X‐ray diffraction study.

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Addition of hydrazine to 4,7-dihydro[1,2
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## Abstract magnified image The 7‐aryl‐4,7‐dihydro[1,2,4]triazolo[1,5‐__a__]pyrimidines **1a**, **1b**, **1c** can undergo addition of hydrazine to the enamine double bond leading to hydrazine derivatives of tetrahydrotriazolopyrimidines **2a**, **2b**, **2c**; the process is usually accompanied by

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## Abstract The reaction of the heterocyclic enamine **1** with tosyl azide (**2**) leads to the tosylimino derivative **4** of 1,2,4‐triazolo[1,5‐a]pyrimidine. The extrusion of nitrogen from the primary adduct **3** is followed by a 1,2‐shift of a methyl group. The structure determination of **4**