4286-87-7Relevant academic research and scientific papers
Synthesis and biological evaluation of novel N-substituted nipecotic acid derivatives with a trans-alkene spacer as potent GABA uptake inhibitors
Tóth, Krisztián,H?fner, Georg,Wanner, Klaus T.
, p. 5944 - 5961 (2018)
Our study presents the synthesis and structure-activity relationship (SAR) of novel N-substituted nipecotic acid derivatives closely related to DDPM-1457 [(S)-2a], a chemically stable analog of (S)-SNAP-5114 (1), in the pursuit of finding new and potent m
Synthesis of Allene Substituted Nipecotic Acids by Allenylation of Terminal Alkynes
Schaarschmidt, Maren,Wanner, Klaus T.
, p. 8371 - 8388 (2017/08/23)
The relative reactivities of several secondary amines serving as hydride donors in propargylic amines undergoing a [1,5]-hydride transfer reaction to yield the respective terminal and 1,3-disubstituted allenes were studied. For this study, a two-step procedure was employed. At first, the synthesis of propargylic amines via the CuI-catalyzed aldehyde-alkyne-amine reactions (A3 coupling) was accomplished. The obtained propargylic amines were subsequently transformed to the desired allenes under CdI2 or ZnI2 catalysis. As a result, among the various secondary amines employed, differing in steric bulk, electronic nature, and conformational properties, allyl(tert-butyl)amine was found to be the best hydride donor for the synthesis of terminal allenes. For the synthesis of 1,3-disubstituted allenes, the propyne derivatives containing either a allyl(tert-butyl)amine or a 1,2,3,6-tetrahydropyridine unit in propargylic position performed best. Finally, with the developed procedure, nipecotic acid derivatives containing an N-allenyl substituent were synthesized with good yields using either ZnI2 as catalyst for the preparation of 1-substituted or CdI2 for the synthesis of 1,3-disubstitued allenes.
Superoxide mediated isomerization of 4-aryl-but-1-ynes to 1-aryl-1,3-butadienes
Khan, Faiz Ahmed,Budanur, Basavaraj M.
, p. 7600 - 7607 (2015/09/07)
A new role of superoxide ion in the isomerization of homobenzylic acetylenes leading to 1-aryl-1,3-butadienes is reported. The unconventional reagent KO2 is found to be superior in performing this kind of isomerization over other the commonly u
