119910-20-2Relevant academic research and scientific papers
Introduction of alkyl groups at the α-positions of pyrrolidines and piperidines: Synthesis of (±)-coniine
Nagasaka, Tatsuo,Hayashi, Hideki,Hamaguchi, Fumiko
, p. 1685 - 1696 (1988)
The conversion of lactams to α-alkylated cyclic amines is described. Reactions of α-ethoxyurethanes with trimethylsilyl cyanide in the presence of Lewis acid afford the corresponding α-cyanourethanes, which, via carbanion, are alkylated to α-alkyl-α-cyanourethanes in moderate to high yields. Syntheses of (±)-coniine and trans-quinolizidine are carried out as model experiments for dealkoxycarbonylation and decyanation of 2-alkyl-1-alkoxycarbonyl-2-cyanopiperidines.
Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
Shono, Tatsuya,Terauchi, Jun,Kitayama, Kenji,Takeshima, Yo-Ichiro,Masumura, Yoshihiro
, p. 8253 - 8262 (2007/10/02)
Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.
