41413-77-8Relevant academic research and scientific papers
Unprecedented 1,4-stannatropy: Effective generation of azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides
Komatsu, Mitsuo,Kasano, Yukihiro,Yonemori, Jin-Ichi,Oderaotoshi, Yoji,Minakata, Satoshi
, p. 526 - 528 (2008/02/05)
Generation and cycloaddition of less- or non-stabilized azomethine ylides, or nitrile ylide equivalents, via unprecedented 1,4-stannatropy of N-(tributylstannylmethyl)thioamides were achieved. The reactions with dipolarophiles, such as electron-deficient alkenes and alkynes, afforded corresponding pyrrolidine and pyrrole derivatives effectively. The Royal Society of Chemistry 2006.
Regioselective Cycloadditions of N-Protonated Azomethine Ylides and 2-Azaallyl Anions Generated from N-(Silylmethyl) Thioimidates, Synthetic Equivalents of Nonstabilized Nitrile Ylides
Tsuge, Otohiko,Kanemasa, Shuji,Yamada, Toshiaki,Matsuda, Koyo
, p. 2523 - 2530 (2007/10/02)
A water-induced-desilylation method and a direct-desilylation method have been applied to N-(silylmethyl) thioimidates to lead to the generation of N-protonated azomethine ylides and 2-azaallyl anions, respectively.These reactive intermediates are capture
A New and General Route to N-Protonated Azomethine Ylides from N-(Silylmethyl)amidines and -thioamides. Cycloaddition of Synthetic Equivalents of Nitrile Ylides
Tsuge, Otohiko,Kanemasa, Shuji,Matsuda, Koyo
, p. 1997 - 2004 (2007/10/02)
The N- or S-alkylation or -silylation of N-(silylmethyl)amidines or -thioamides and the subsequent desilylation of the silylmethyl group generate N-protonated azomethine ylides bearing a leaving group.These azomethine ylides undergo successful cycloaddition with electron-deficient olefins, acetylenes, and aldehydes.As the leaving group is eliminated under the reaction conditions, these azomethine ylides can be synthetic equivalents of nonstabilized nitrile ylides which are otherwise relatively inaccessible.
WATER-INDUCED AZOMETHINE YLIDE GENERATION FROM N-(SILYLMETHYL)THIOIMIDATES, SYNTHETIC EQUIVALENTS OF NONSTABILIZED NITRILE YLIDES
Tsuge, Otohiko,Kanemasa, Shuji,Yamada, Toshiaki,Matsuda, Koyo
, p. 2489 - 2492 (2007/10/02)
N-(Silylmethyl)thioimidates undergo a water-induced desilylation generating azomethine ylide 1,3-dipoles which cycloadd to a variety of electron-deficient olefins providing 1- or 2-pyrrolines after the elimination of thiol, indicating that the thioimidate
N-PROTONATED AZOMETHINE YLIDES WITH A LEAVING GROUP AS SYNTHETIC EQUIVALENTS FOR NONSTABILIZED NITRILE YLIDES
Tsuge, Otohiko,Kanemasa, Shuji,Matsuda, Koyo
, p. 1411 - 1414 (2007/10/02)
Through alkylation or silylation and then desilylation steps, N-(silylmethyl)amidines generate N-protonated azomethine ylides which cycloadd to olefins, acetylenes, and aldehydes giving 1- or 2-pyrrolines, pyrroles, and 2-oxazolines, respectively, after the elimination of N-substituted anilines.With this sequence, the amidines are useful synthetic equivalents of nonstabilized nitrile ylides.
