108975-90-2Relevant academic research and scientific papers
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.
Remarkable [3+2] annulations of electron-rich olefins with unstabilized azomethine ylides
Davoren, Jennifer E.,Gray, David L.,Harris, Anthony R.,Nason, Deane M.,Xu, Wenjian
experimental part, p. 2490 - 2492 (2010/12/20)
Herein we would like to communicate that an unstabilized azomethine ylide generated from commercial trimethylamine N-oxide will undergo a remarkable 1,3-dipolar cycloaddition in good yield with electron-rich and unpolarized olefins. A broad range of substituents on the alkenes are tolerated provided they are compatible with excess LDA. This demonstration of novel reaction scope should encourage others to try trimethylamine N-oxide as an azomethine ylide precursor in the synthesis of challenging 3,4-disubstituted pyrrolidines. Georg Thieme Verlag Stuttgart New York.
Deprotonation de N-oxydes d'amines aliphatiques: schema reactionnel general et nouvelle synthese de pyrrolidines
Beugelmans, Rene,Benadjila-Iguertsira, Leila,Chastanet, Jacqueline,Negron, Guillermo,Roussi, Georges
, p. 725 - 734 (2007/10/02)
Amine oxides, 1, 5, 10, 15, 21, 23, when treated by lithium diisopropylamide undergo deprotonation.Monodeprotonation gives rise either to secondary amines and benzaldehyde resulting from the hydrolysis of an intermediate immonium (I) or to hydroxylamines via a Stevens-like rearrangement observed for the first time on an amine oxide.Double deprotonation gives an immonium ylid (Y) which, depending upon the structure of the initial tertiary amine yields either "head to head" piperazines (biradical-like behavior of (DD)) or aziridines.The immonium ylid (Y5) derived from trimethylamine oxide, whose formation and reactivity are reported for the first time, has remarkable property of undergoing cycloaddition reactions with unactivated olefins, leading to a new and efficient synthesis of various pyrrolidines.
Trimethylamine N-Oxide as a Precursor of Azomethine Ylides
Beugelmans, R.,Negron, G.,Roussi, G.
, p. 31 - 32 (2007/10/02)
The first azomethine ylide devoid of a stabilizing group, generated by treating trimethylamine N-oxide with lithium di-isopropylamide, undergoes a ready cycloaddition with various simple alkenes to give high yields of the corresponding pyrrolidine
