32687-33-5Relevant 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
Nitrogen-Radical-Triggered Trifunctionalizing ipso-Spirocyclization of Unactivated Alkenes with Vinyl Azides: A Modular Access to Spiroaminal Frameworks
Qi, Zhongyu,Zhang, Zhijie,Yang, Li,Zhang, Di,Lu, Ji,Wei, Jun,Wei, Siping,Fu, Qiang,Du, Xi,Yi, Dong
supporting information, p. 3762 - 3768 (2021/07/16)
We report an example of non-dearomative trifunctionalizing ipso-spirocyclization of unactivated alkenes through photoredox-catalyzed, nitrogen-radical-triggered cyclization-trapping-translocation-cyclization cascade, providing a single-step modular access to spiroaminal frameworks through the sequential formation of one C?C bond and two geminal C?N bonds. The developed protocol utilizes not only internal and terminal olefinic oxime esters, but also olefinic amides as nitrogen radical precursors, and features a broad substrate scope, wide functional group compatibility, easy scalability, and potential for product derivatization and late-stage functionalization of bioactive estrone derivatives. Importantly, the mechanistic studies including DFT calculations indicate that the photocatalytic trifunctionalizing ipso-spirocyclization undergoes a radical relay cascade of intramolecular 5-exo-trig cyclization, intermolecular radical trapping, 1,5-hydrogen atom transfer, and sequential 5-endo-trig cyclization, which provides another reaction mode of alkenes. (Figure presented.).
Visible-Light-Induced Regioselective C(sp3)-H Acyloxylation of Aryl-2 H-azirines with (Diacetoxy)iodobenzene
De, Aramita,Santra, Sougata,Hajra, Alakananda,Zyryanov, Grigory V.,Majee, Adinath
, p. 11735 - 11740 (2019/10/02)
A visible-light-promoted regioselective coupling of C(sp3)-H of aryl-2H-azirine and (diacetoxy)iodobenzene has been reported. Rose Bengal as an organophotoredox catalyst has been used in this reaction. The reaction proceeds under aerobic condition at room temperature. A variety of aryl-2H-azirines gives the corresponding acyloxylated azirines under this reaction conditions. The reaction goes through a radical pathway. The protocol is also applicable on gram-scale synthesis.
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.
Synthesis of unsymmetrical pyrazines based on ?±-diazo oxime ethers
Loy, Nicole S. Y.,Kim, Sunggak,Park, Cheol-Min
supporting information, p. 395 - 397 (2015/03/03)
Synthesis of unsymmetrically substituted pyrazines has been a challenge. The reactivity of ?±-imino carbenoids derived from ?±-diazo oxime ethers has been exploited for pyrazine synthesis, in which the reaction of ?±-diazo oxime ethers with 2H-azirines provides highly substituted pyrazines in good to excellent 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
supporting information, 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
