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Cyclocondensation of 6-acetyl-4,7-dihydro-5-methyl-7-phenyl[1,2,4]triazolo[1,5-a]pyrimidine with hydroxylamine and hydrazine

✍ Scribed by Sergey M. Desenko; Sergey A. Komykhov; Valery D. Orlov; Herbert Meier

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
164 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The cyclocondensation of 6‐acetyl‐4,7‐dihydro‐5‐methyl‐7‐phenyl[1,2,4]triazolo[1,5‐a]pyrimidine (3) with hydroxylamine or hydrazine leads to 3a,4,9,9a‐tetrahydro‐3,9a‐dimethyl‐4‐phenylisoxazolo‐[5,4‐d][1,2,4]triazolo[1,5‐a]pyrimidine (4a) and 3a,4,9,9a‐tetrahydro‐3,9a‐dimethyl‐4‐phenyl‐1__H__‐pyrazolo[3,4‐d][1,2,4]triazolo[1,5‐a]pyrimidine (4b), respectively. In the presence of methanolic hydrogen chloride, 4b undergoes a cleavage of the pyrimidine ring to yield (5‐amino‐1,2,4‐triazol‐1‐yl)(3,5‐dimethylpyrazol‐4‐yl)phenylmethane (5). The structure determination of the compounds obtained is based on ^1^H and ^13^C nmr spectra including NOE measurements.

📜 SIMILAR VOLUMES

Addition of hydrazine to 4,7-dihydro[1,2
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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**