70766-02-8Relevant articles and documents
Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines
Hirazawa, Yoshinobu,Kadota, Tetsuya,Kondo, Yuta,Morimoto, Hiroyuki,Morisaki, Kazuhiro,Ohshima, Takashi
, p. 120 - 125 (2020/02/20)
N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.
X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 21 ACTIVATION OF THE ZH PROTON IN IMINES.
Grigg, Ronald,Donegan, Gregory,Gunaratne, H. Q. Nimal,Kennedy, Deirdre A.,Malone, John F.,et al.
, p. 1723 - 1746 (2007/10/02)
Imines, RCH=N-ZH, possessing a range of ZH groups (Z=CHCOPh, CHCOSR, CHCONHR, CHP(O)(OEt)2, 2-CH-pyridyl, 2-CH-thiazolyl, and 9-fluorenyl) undergo thermal 1,2-prototropy generating azomethine ylides stereospecifically.The intermediate azomethine ylides un
The Synthesis of NH Aldimines and Derivatives by Spontaneous and Base-catalysed Decomposition of Oxaziridines
Boyd, Derek R.,Coulter, Peter B.,Hamilton, Robert,Thompson, Norris T.,Sharma, Narain D.,Stubbs, Michael E.
, p. 2123 - 2128 (2007/10/02)
A range of oxaziridines containing N-methylene substituents has been synthesized by peracid oxidation of the corresponding fluorenylidene N-alkylamines.Spontaneous and tertiary amine base-catalysed decomposition of the oxaziridines into unstable NH aldimines and derivatives was observed.Acrylaldehyde, 2-methylacrylaldehyde, and benzaldehyde NH imines have been identified as initial products from decomposition of the corresponding oxaziridines. 2,4,6-Trialkylhexahydro-1,3,5-triazines, N,N'-dialkylidene-1,1-diaminoalkanes, N,N'-diarylidene-1,1-diaminoalkanes, and N-isobutylidene-2-methylpropenylamine were among the isolated products formed via the undetected alkyl aldehyde NH imines resulting from oxaziridine decomposition.