56475-87-7Relevant articles and documents
A New Method for Introducing Some Active Methylene or Methine Groups to the 3-Position of Pyrrolidine or Piperidine Skeleton, and Its Application to Preparation of a Key Intermydiate for (+/-)-Eburnamonine Synthesis
Shono, Tatsuya,Matsumura, Yoshihiro,Ogaki, Masaru,Onomura, Osamu
, p. 1447 - 1450 (1987)
A new method for introducing a bis(methoxycarbonyl)methyl or 2-oxopropyl group to the 3-position of pyrrolidine or piperidine skeleton has been exploited, and this method could be used in the synthesis of a key intermediate for the (+/-)-eburnamonine synthesis.
Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy
Merx, Jona,Houthuijs, Kas J.,Elferink, Hidde,Witlox, Eva,Mecinovi?, Jasmin,Oomens, Jos,Martens, Jonathan,Boltje, Thomas J.,Rutjes, Floris P. J. T.
supporting information, (2022/01/06)
N-Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N-acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N-acyliminium ions.
A new and efficient synthesis of derivatives of octahydro-4H-pyrrolo[1,2-c] pyrido[1′,2′-a]imidazole
Rouchaud, Anne,Braekman, Jean-Claude
experimental part, p. 2346 - 2353 (2011/06/22)
When diethyl malonate was added to a solution of Δ1- piperideine, generated in situ by oxidative desamination and decarboxylation of L-lysine by N-bromosuccinimide (NBS), formation of the unexpected tricyclic compound 6 (4-diethylmalonyl-octahydro-4H-pyrrolo[1,2-c]pyrido[1′, 2′-a]imidazole)was observed. The structure of 6 was deduced from analysis of its spectroscopic data and was confirmed both by chemical degradation and by total synthesis. We proved that 3-bromo-1-piperideine was implicated in its formation. Moreover, based on this feature, a new and efficient synthesis of 6 was developed. The elaborated pathway was adapted to access derivatives related to 6 that differed in their C-4 substituent. A new and efficient synthesis of derivatives of the tricyclic heterocycle A from lysine is described. A mechanism involving 3-halopiperideines as intermediates and based on a ring contraction followed by Michael reaction is proposed and tested. Copyright
Stereoselective synthesis of azasugars by electrochemical oxidation
Furukubo, Shigeru,Moriyama, Noriaki,Onomura, Osamu,Matsumura, Yoshihiro
, p. 8177 - 8181 (2007/10/03)
A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-prote