Conversion of 4,6-disubstituted pyrimidines into 1,2,4-Triazoles by action of Hydrazine
✍ Scribed by H. C. van der Plas; H. Jongejan
- Book ID
- 104587928
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 320 KB
- Volume
- 89
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
4,6‐Diethoxy‐, 4‐ethoxy‐6‐hydrazino‐, 4,6‐dichloro‐, 4,6‐di(methylthio)‐and 4,6‐dihydrazinopyrimidine react with aqueous hydrazine at 210° to give 3‐methyl‐1,2,4‐triazole. Evidence is presented that in this unprecedented ring contraction reaction the C(2)‐N(3 or 1)‐C(4 or 6)‐C(5) fragment of the pyrimidine ring is involved in the formation of this 1,2,4‐triazole.
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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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