24963-10-8Relevant academic research and scientific papers
Electrochemical oxidative annulation of amines and aldehydes or ketones to synthesize polysubstituted pyrroles
Gao, Xinlong,Wang, Pan,Wang, Qingqing,Chen, Jingting,Lei, Aiwen
supporting information, p. 4941 - 4945 (2019/09/30)
A general and practical protocol to synthesize polysubstituted pyrroles has been established by electrooxidative annulation of amines and aldehydes or ketones. In an undivided cell, arylacetaldehydes and primary amines can participate in this transformati
Tetrahydropyrrolization of Resveratrol and Other Stilbenes Improves Inhibitory Effects on DNA Oxidation
Bao, Liang-Liang,Liu, Zai-Qun
, p. 1617 - 1625 (2016/08/28)
The inhibitory effect of resveratrol on DNA oxidation caused by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH) was found to be enhanced if the C=C bond in resveratrol was converted into tetrahydropyrrole by reaction with azomethine ylide (CH2=N+(CH3)CH2?). This encouraged us to explore whether the inhibitory activities of other stilbenes could also be increased by the same method. We found that the inhibitory effects of the tetrahydropyrrole derivatives on AAPH-induced oxidation of DNA were higher than those of the corresponding stilbenes, because the tetrahydropyrrole motif can provide hydrogen atoms to be abstracted by radicals. Therefore, the tetrahydropyrrolization offered an advantage for enhancing the antioxidant effects of stilbenes. Notably, (CH3)3SiCH2N(CH3)CH2OCH3(in the presence of CF3COOH) and (CH3)3NO (in the presence of LiN(iPr)2) can be used to generate azomethine ylide for the tetrahydropyrrolization of stilbenes containing electron-withdrawing and -donating groups, respectively.
An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides
Zhang, Weimin,Ning, Fuqiang,Váradi, Linda,Hibbs, David E.,Platts, James A.,Nyerges, Miklós,Anderson, Rosaleen J.,Groundwater, Paul W.
, p. 3621 - 3629 (2014/05/20)
Substituents on the diene component have little influence on the periselectivity of the cyclizations of α,β:γ,δ-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6π) and 1,7-electrocyclization (8π) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration.
THE CYCLOADDITION REACTION OF NONSTABILIZED AZOMETHINE YLIDE GENERATED FROM TRIMETHYLAMINE N-OXIDE TO CC, C=N AND C=S BONDS
Beugelmans, Rene,Chastanet, Jacqueline,Roussi, Georges
, p. 3197 - 3202 (2007/10/02)
The reported cycloaddition reactions between nonstabilized azomethine ylide Y generated from trimethylamine N-oxide 1 and unactivated CC 2 - 4, C=N 5 and C=S 6, 7 bonds constitute an attractive entry respectively to pyrrolines and pyrroles 10 - 13, imi
Dinitrones from C-Benzyl Nitrones
Sarlo, Francesco De,Brandi, Alberto,Guarna, Antonio
, p. 1395 - 1398 (2007/10/02)
N,N'-Dialkyl- and diaryl-dinitrones of the 2,3-diphenylbutanediylidenebisamine N,N'-dioxide (3) are shown to be intermediates in the spontaneous conversion of C-benzyl nitrones (1) into the diphenylpyrroles (4) or 2,3-diphenylprop-2-en-1-al (5).The proces
