110678-64-3Relevant academic research and scientific papers
Regitz Diazo Transfer Reaction for the Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles and Subsequent Regiospecific Construction of 1,4-Disubstituted 1,2,3-Triazoles via C-C Bond Cleavage
Cui, Xue,Zhang, Xueying,Wang, Wei,Zhong, Xia,Tan, Yinfeng,Wang, Yan,Zhang, Jianlan,Li, Youbin,Wang, Xuesong
, p. 4071 - 4080 (2021)
A straightforward and efficient methodology has been developed for the synthesis of 1,4,5-trisubstituted dicarbonyl 1,2,3-triazoles and 1,4-disubstituted sole-carbonyl 1,2,3-triazoles via a C-C bond cleavage process. The Regitz diazo transfer and C-C bond cleavage were the key steps of this transformation, which provided diverse carbonyl-substituted structural 1,2,3-triazoles. This reaction featured with excellent regioselectivity, wide functional group tolerance, and mild conditions.
Photolysis of 1-Aryl-1,2,3-triazoles; Rearrangement via !H-Azirines
Mitchell, Glynn,Rees, Charles W.
, p. 413 - 422 (2007/10/02)
The preparation and photolysis of a series of 1-(1-naphthyl)-1,2,3-triazoles, (2)-(5), and of 1-(2-methyl-1-naphthyl)-1,2,3-triazoles, (6)-(9), with and without electron-withdrawing groups (CO2R, CONH2, CN, CHO, COPh) in the triazole ring, are described.In the first series, triazoles (3) with two electron-withdrawing groups, and triazoles (4) with one such group at C-4, mostly give good yields of the expected benzindoles (10) and 11 respectively.Triazoles (5) with the electron-withdrawing group at C-5 also give benzindoles but these are now mixtures of the expected (12) and rearranged indoles (11).Photolysis of the 1-phenyltriazoles (21) and (22) follows the same pattern, those with the electron-withdrawing group at C-5 rearranging to give mixtures of indoles (23) and (24).This is explained by a mechanism (Scheme 3) in which the less stable carbene intermediate (13) rearranges to the more stable carbene (15) via the 1H-azirine (14), in competition with its direct cyclisation.This provides the first evidence for antiaromatic 1H-azirines as intermediates in a photochemical reaction.Photolysis of the 2-methylnaphthyl compounds follows a different path: diester (7b) and dinitrile (7d) give high yields of the deeply coloured 9-methyl-1H-benzoquinoline derivatives (25a) and (25b) respectively, the first stable examples of this ring system to be isolated.Photolysis of the nitrile (8c) gives 9b-methyl-9bH-benzindole-3-carbonitrile (28), a rare example of a stable indole with a ring junction substituent. 1,2-Shifts in the carbenes are only observed with the bis(trimethylsilyl)triazoles (2d) and (6f), in keeping with the known rapid migration of trimethylsilyl groups to carbene centres.
