51659-21-3Relevant academic research and scientific papers
Asymmetric aziridination of chalcone promoted by binaphthalene-based chiral amines
Page, Philip C. Bulman,Bordogna, Céline,Strutt, Ian,Chan, Yohan,Buckley, Benjamin R.
, p. 2067 - 2072 (2013)
Aminimines derived in situ from a number of enantiomerically pure binaphthalene-based tertiary amines have been used for the asymmetric aziridination of chalcone, providing N-unprotected aziridines with ee values of up to 43%. A chiral hydrazinium salt has been isolated for the first time and shown to provide similar yield and enantioselectivity to the in situ process in reaction with chalcone. Georg Thieme Verlag Stuttgart, New York.
Synthesis of aziridines by electrochemical oxidative annulation of chalcones with primary amines
Gu, Lijun,He, Yonghui,Li, Ganpeng,Zeng, Dongwen,Zhang, Lizhu
, (2021/12/01)
Synthesis of aziridines by electrochemical oxidative annulation of chalcone 1,3-diphenyl-2-propen-1-one with primary amines has been developed under external oxidant - and base-free conditions. The reaction constitutes a new transformation of chalcones with primary amines to aziridines, providing a complementary, simple, and environmentally friendly approach to the currently available methods. A reaction mechanism for this transformation has been proposed based on the cyclic voltammetry.
On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine
Danahy, Kelley E.,Styduhar, Evan D.,Fodness, Aria M.,Heckman, Laurel M.,Jamison, Timothy F.
supporting information, p. 8392 - 8395 (2020/11/18)
Herein, we demonstrate the on-demand synthesis of chloramine from aqueous ammonia and sodium hypochlorite solutions, and its subsequent utilization as an ambiphilic nitrogen source in continuous-flow synthesis. Despite its advantages in cost and atom economy, chloramine has not seen widespread use in batch synthesis due to its unstable and hazardous nature. Continuous-flow chemistry, however, provides an excellent platform for generating and handling chloramine in a safe, reliable, and inexpensive manner. Unsaturated aldehydes are converted to valuable aziridines and nitriles, and thioethers are converted to sulfoxides, in moderate to good yields and exceedingly short reaction times. In this telescoped process, chloramine is generated in situ and immediately used, providing safe and efficient conditions for reaction scale-up while mitigating the issue of its decomposition over time.
Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines
Samimi, Heshmat A.,Momeni, Ahmad R.
, p. 2221 - 2225 (2015/10/19)
A new approach for the synthesis of N-H ketoaziridines is described. 1-aminopyridinium iodide as a NH transferring agent provides a straightforward access to the 2-aroyl-3-arylaziridines from the corresponding 1,3-diarylprop-2-en-1-one. A possible general mechanism involving the N-N ylide is proposed.
Efficient aziridination of α,β-unsaturated ketones with O-(2,4-dinitrophenyl)-hydroxylamine
Wang, Jin-Jia,Lao, Jin-Hua,Li, Xue-Ming,Lu, Rui-Jiong,Miao, Hui,Yan, Ming
experimental part, p. 1577 - 1584 (2012/05/05)
The aziridination of α,β-unsaturated ketones with O-(2,4-dinitrophenyl)-hydroxylamine and tertiary amine was developed. trans-Aziridines were obtained exclusively in good yields. The reaction is proposed to occur via an aminimide intermediate. Copyright T
Amine-promoted, organocatalytic aziridination of enones
Armstrong, Alan,Baxter, Carl A.,Lamont, Scott G.,Pape, Andrew R.,Wincewicz, Richard
, p. 351 - 353 (2007/10/03)
(Chemical Equation Presented) A novel method is presented using N-N ylides (prepared by in situ amination of a tertiary amine) for the aziridination of a range of enone systems. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter.
N-amino-N-methylmorpholinium salts: Highly active aziridination reagents for chalcones
Armstrong, Alan,Carbery, David R.,Lamont, Scott G.,Pape, Andrew R.,Wincewicz, Richard
, p. 2504 - 2506 (2008/02/11)
A highly effective aziridination reagent, based on N-methylmorpholine, is reported which effects rapid conversion of chalcones to N-unfunctionalised aziridines at room temperature. Georg Thieme Verlag Stuttgart.
Facile preparation of allyl amines and pyrazoles by hydrazinolysis of 2-ketoaziridines
Chen, Gang,Sasaki, Mikio,Yudin, Andrei K.
, p. 255 - 259 (2007/10/03)
Allyl amines and pyrazoles can be obtained by hydrazinolysis of 2-ketoaziridines. A variety of aziridines, including N-unprotected, N-substituted, as well as bicyclic enamine and aminal type, can be transformed into diversely substituted linear or cyclic products. The hydrazinolysis of homochiral aziridines proceeds without racemization.
An amine-promoted aziridination of chalcones
Shen, Yu-Mei,Zhao, Mei-Xin,Xu, Jiaxi,Shi, Yian
, p. 8005 - 8008 (2007/10/03)
(Chemical Equation Presented) Without protection: α-Keto aziridines have been formed in a novel amine-promoted direct aziridination of chalcones using an aminimide generated in situ from a tertiary amine and O-mesitylenesulfonylhydroxylamine (MSH) in the
Direct NH-aziridination of α,β-unsaturated ketones
Xu, Jiaxi,Jiao, Peng
, p. 1491 - 1493 (2007/10/03)
1-Aryl-α,β-unsaturated ketones were directly aziridinated, N-unsubstituted, in a one-pot reaction with satisfactory yields by N,N′-diamino-1,4-diazoniabicyclo[2.2.2]octane dinitrate, a nitrogen-nitrogen ylide precursor, in the presence of sodium hydride.
