25856-06-8Relevant academic research and scientific papers
Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process
Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun
, p. 8502 - 8506 (2021/10/20)
Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.
A new synthetic strategy towards 2,4,5-trisubstituted 1H-imidazoles and highly substituted pyrrolo[1,2-c]imidazoles by use of α-azidochalcones via Michael addition-cyclization followed by Wittig reaction
Adib, Mehdi,Peytam, Fariba,Rahmanian-Jazi, Mahmoud,Bijanzadeh, Hamid Reza,Amanlou, Massoud
, p. 6696 - 6705 (2017/10/25)
Efficient and facile protocols for the preparation of highly functionalized 1H-imidazoles and 5H-pyrrolo[1,2-c]imidazoles are described. Heating a mixture of an α-azidochalcones and N,N,N′,N′-tetramethyl guanidine under neat conditions gave the corresponding 2,4,5-trisubstituted 1H-imidazole via Michael addition-cyclization in excellent yields. Subsequently, the prepared 1H-imidazoles undergo addition-Wittig reaction with acetylenic esters in presence of triphenylphosphine in dichloromethane to afford 5H-pyrrolo[1,2-c]imidazoles in high yields.
Visible-light photoredox catalysis enabled bromination of phenols and alkenes
Zhao, Yating,Li, Zhe,Yang, Chao,Lin, Run,Xia, Wujiong
, p. 622 - 627 (2014/04/17)
A mild and efficient methodology for the bromination of phenols and alkenes has been developed utilizing visible light-induced photoredox catalysis. The bromine was generated in situ from the oxidation of Br- by Ru(bpy)33+, both of which resulted from the oxidative quenching process.
One-pot three-component approach to the synthesis of polyfunctional pyrazoles
Zhang, Guolin,Ni, Hangcheng,Chen, Wenteng,Shao, Jiaan,Liu, Huan,Chen, Binhui,Yu, Yongping
supporting information, p. 5967 - 5969 (2014/01/06)
A simple, multicomponent, and straightforward reaction of vinyl azide, aldehyde, and tosylhydrazine affords the construction of 3,4,5-trisubstituted 1H-pyrazoles regioselectively in the presence of base with moderate to excellent yields. A range of functionality could be tolerated in this methodology, and a possible mechanism is proposed.
Chemoselective C-C bond cleavage of epoxide motifs: Gold(I)-catalyzed diastereoselective [4+3] cycloadditions of 1-(1-Alkynyl)oxiranyl ketones and nitrones
Wang, Tao,Zhang, Junliang
scheme or table, p. 86 - 90 (2011/03/20)
Cutting carbon! A novel facile strategy for the C-C bond cleavage of oxiranyl ketones has been developed. Carbophilic gold(I) activation of the alkyne side chain mediates a heterocyclization and subsequent C-C bond cleavage (see scheme).
Solvolytic stereoselective debromination of vic-dibromides with HMPA
Khurana,Bansal,Chauhan
, p. 1089 - 1091 (2007/10/03)
A simple and efficient procedure for the debromination of vic-dibromides has been reported with hexamethylphosphoric triamide at 155-160°C under a nitrogen atmosphere without the aid of any reagent.
New Derivatives of N-Vinyltriazoles: 1,3-Diaryl-3-(1H-1,2,4-triazol-1-yl)-2-propen-1-ones
Rekhter, M. A.,Grushetskaya, G. N.,Panasenko, A. A.,Krimer, M. Z.
, p. 792 - 796 (2007/10/03)
We have synthesized previously unknown N-vinyltriazoles: 1,3-diaryl-3-(1H-1,2,4-triazol-1-yl)-2-propen-1-ones.We discusss a hypothesis for a probable reaction mechanism.
Imidazo[2,1-b]thiazole derivatives XII. Synthesis and immunoactivity in vitro on human T lymphocyte of several 3-aroylmethyl and 2-aroyl-3-methyl(aryl)-5,6-dihydroimidazo[2,1-b]thiazoles
Robert,Hassanine,Harraga,Seilles
, p. 261 - 271 (2007/10/02)
To estimate the influence of aryl group position on the immunostimulant properties of imidazo[2,1-b]thiazole derivatives, several compounds were obtained and tested, versus tetramisole hydrochloride, on the mobilisation of CD2 receptor by human T lymphocyte. The synthesis use the action of monobrominated β-diketones on the 2-mercaptoimidazoline. So, 1-aryl-4-bromobutane-1,3-diones lead to 3-aroylmethyl-5,6-dihydroimidazo[2,1-b]thiazoles 4. Same, 1-aryl-2-bromobutane-1,3-diones and 1,3-diaryl-2-bromopentane-1,3-diones give respectively 3-aroyl-2-methyl-5,6-dihydroimidazo[2,1-b]thiazoles 5 and 3-aroyl-2-aryl-5,6-dihydroimidazo[2,1-b]thiazoles 6. Better yields are obtained when the reaction presents two steps. The first one, realized in acetone at room temperature, leads to an intermediate S-substituted 4,5-dihydroimidazole which, in second step, is cyclized in imidazo[2,1-b]thiazole compound via an unisolated carbinolamine. This one explains the univocal formation of 5 derivatives and the feasible blending in case of 6. The immunoactivity of several imidazothiazoles 4, 5 and 6 is lower that them of 6-aryl substituted compounds and particularly that the levamisole which is the reference product in this series.
