1,2-Methyl shift in the reaction of 4,7-dihydro-4,5-dimethyl-7-phenyl-(1,2,4)-triazolo[1,5-a]pyrimidine with tosyl azide
✍ Scribed by Sergey A. Komykhov; Sergey M. Desenko; Alexander S. Kaganovsky; Valery D. Orlov; Herbert Meier
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2000
- Tongue
- English
- Weight
- 115 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
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 is based on ^1^H and ^13^C nmr spectra including NOE measurements.
📜 SIMILAR VOLUMES
## 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‐dimeth
## 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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