- Synthesis of 2-Substituted 1,2,3-Triazoles via an Intramolecular N–N Bond Formation
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An efficient synthesis of 2-aryl 1,2,3-triazoles based on an intramolecular N–N bond formation is described. Selective activation of bis-hydrazone at the dimethylamino hydrazone group with MeI forms a mono-hydrazonium species. Treatment of the hydrazonium
- Chen, Cheng-yi,Lu, Xiaowei,Holland, Mareike C.,Lv, Shichang,Ji, Xuebao,Liu, Wei,Liu, Jie,Depre, Dominique,Westerduin, Pieter
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supporting information
p. 548 - 551
(2019/12/24)
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- Addition of Semidione Radicals to Arenediazonium Ions: Synthesis of 1,1-Diacyl-2-arylhydrazines
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The α-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET).When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5).A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.
- Clerici, Angelo,Porta, Ombretta
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p. 6813 - 6818
(2007/10/02)
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