32687-34-6Relevant academic research and scientific papers
A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach
Andresini, Michael,Degannaro, Leonardo,Luisi, Renzo
, p. 203 - 209 (2021/02/26)
The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds. The protocol has been developed using c
Zn-ProPhenol Catalyzed Enantioselective Mannich Reaction of 2 H-Azirines with Alkynyl Ketones
Trost, Barry M.,Zhu, Chuanle
, p. 9683 - 9687 (2020/12/21)
The enantioselective Mannich reaction of 2H-azirines with alkynyl ketones is achieved under Zn-ProPhenol catalysis, delivering various aziridines with vicinal tetrasubstituted stereocenters in high yields with excellent enantioselectivities. The bimetalli
Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines
Baek, Yonghyeon,Maeng, Chanyoung,Kim, Hyunseok,Lee, Phil Ho
, p. 2349 - 2360 (2018/02/23)
A regioselective synthetic method for the preparation of indolopyrazines was demonstrated through a sequential Rh-catalyzed formal [3+3] cycloaddition and aromatization reaction of a wide range of diazoindolinimines with azirines. Because the previously reported synthetic methods afforded mixtures of indolopyrazines, the present method using unsymmetrical azirines has a strong advantage from a regioselectivity viewpoint.
Synthesis, structure and photophysical properties of NIR aza-BODIPYs with [sbnd]F/[sbnd]N3/[sbnd]NH2 groups at 1,7-positions
Jiang, Xin-Dong,Guan, Jian,Zhao, Jiuli,Le Guennic, Boris,Jacquemin, Denis,Zhang, Zhigang,Chen, Shangdong,Xiao, Linjiu
, p. 619 - 626 (2016/09/23)
With 4-fluorostyrene as the starting material, symmetric/asymmetric fluorine-containing aza-difluoroboradiaza-s-indacenes (aza-BODIPYs) 3–6?at 1/7-position were successfully prepared. NaN3 undertook nucleophilic aromatic substitution via replac
Enantioselective Reaction of 2H-Azirines with Phosphite Using Chiral Bis(imidazoline)/Zinc(II) Catalysts
Nakamura, Shuichi,Hayama, Daiki
supporting information, p. 8785 - 8789 (2017/07/17)
The first highly enantioselective nucleophilic addition reaction of phosphites with 2H-azirines has been developed. The reaction was applied to various 3-substituted 2H-azirines using novel chiral bis(imidazoline)/ZnII catalysts to afford produ
Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton
Chen, Lili,Li, Hongji,Li, Pinhua,Wang, Lei
, p. 3646 - 3649 (2016/08/16)
A novel three-component cyclization of 2H-azirines, alkynyl bromides, and molecular oxygen under visible-light photoredox catalysis at room temperature has been developed, which provides a direct approach to a wide range of substituted oxazoles in moderate to good yields.
Rh(ii)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: Switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon
Wang, Yuanhao,Lei, Xiaoqiang,Tang, Yefeng
, p. 4507 - 4510 (2015/03/18)
The Rh(ii)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions. This journal is
Exploiting the chemistry of strained rings: Synthesis of indoles via domino reaction of aryl iodides with 2 H-azirines
Candito, David A.,Lautens, Mark
supporting information; experimental part, p. 3312 - 3315 (2010/10/19)
(Equation Presented). The highly strained 2H-azirine ring system has been the source of considerable theoretical and synthetic work. The reaction of these strained heterocycles with transition metals has been documented to give rise to ring opening and subsequent formation of varied heterocycles. An interesting domino reaction is described wherein the strained bicyclic alkene, norbornene, mediates the reaction of 2H-azirines with aryl iodides under palladium catalysis to provide indole or polycyclic dihydroimidazole heterocycles.
