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Citation: Liu Yi, Liu Xianjun, Wang Quanrui. Synthesis of 1,3,5-Trisubstituted 1H 1,2,4-trazoles from Pinakolone[J]. Chinese Journal of Applied Chemistry, ;1999, 16(5): 73-75. shu

Synthesis of 1,3,5-Trisubstituted 1H 1,2,4-trazoles from Pinakolone

1.
Department of Chemistry, Fudan University, Shanghai 200433

Received Date: 1 February 1999
Available Online: 13 April 1999
Fund Project: 国家自然科学基金资助项目(29872007) (29872007)

1-Aza-2-azoniaallene cations 3(denoted also as azo carbenium ions) were generated in situ as reactive intermediates by chlorination of pinakolone hydrazones 1 with tert-butyl hypochlorite and treatment of the resulted(1-choroalkyl)azo compounds 2 with a Lewis acid (SbCl₅). The allene like cations 3 were trapped by cycloaddition to the triple bond of nitriles giving 3H 1,2,4-triazolium salts 4. The initially formed heterocycles 4 couldn't be isolated but underwent smooth 1,2-tert butyl shift accompanied by elimination of isobutene to afford 1H-1,2,4 triazolium salts 5, from which 1,3,5-trisubstituted-1H 1,2,4 triazoles 6 have been obtained in moderate to high yields after basic work-up. Heterocycles 6 are characterized by elemental analysis and IR, ¹H NMR measurements.
- 1H-triazole,
- synthesis,
- pinakolone,
- aza azoniaallene cation,
- cycloaddition
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