88855-24-7Relevant academic research and scientific papers
Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO
Heindl, Sebastian,Lemmerer, Miran,Malzer, Nicolas,Matyasovsky, Ján,Maulide, Nuno,Riomet, Margaux
, p. 19123 - 19127 (2021/07/26)
A chemoselective and robust protocol for the γ-oxidation of β,γ-unsaturated amides is reported. In this method, electrophilic amide activation, in a rare application to unsaturated amides, enables a regioselective reaction with TEMPO resulting in the title products. Radical cyclisation reactions and oxidation of the synthesised products highlight the synthetic utility of the products obtained.
A Facile Synthesis of 3,4-Dienamides by the Reaction of Propargyl Alcohols with Cyclic Amide Acetals and Their Stereoselective Rearrangement to 2(E),4(Z)-Dienamides Promoted with Alumina. Total Synthesis of Isochavicine
Tsuboi, Sadao,Nooda, Yuji,Takeda, Akira
, p. 1204 - 1208 (2007/10/02)
Thermal condensation of propargyl alcohols with acetals of 1-acetylpyrrolidine and 1-acetylpiperidine gave 3,4-dienamides in good yields.Alumina promoted the rearrangement of β-allenic amides to 2(E),4(Z)-dienamides stereoselectively.Its application to the synthesis of isochavicine of pepper components is described.Carbon-13 NMR data of these dienamides were obtained.
