141544-15-2Relevant academic research and scientific papers
Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies
Grams, R. Justin,Lawal, Monsurat M.,Szwetkowski, Connor,Foster, Daniel,Rosenblum, Carol Ann,Slebodnick, Carla,Welborn, Valerie Vaissier,Santos, Webster L.
supporting information, p. 172 - 178 (2021/10/14)
We report a chemoselective, phosphine-catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n-tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with (E)-stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α-carbon and the proton on the amide nitrogen is abstracted by the ?-carbon to furnish the (E)-acrylamides. DFT calculations revealed a clear energetic driving force for the (E)- over the (Z)-isomer. (Figure presented.).
Catalytic, transition-metal-free semireduction of propiolamide derivatives: Scope and mechanistic investigation
Grams, R. Justin,Garcia, Christopher J.,Szwetkowski, Connor,Santos, Webster L.
supporting information, p. 7013 - 7018 (2020/09/12)
We report a transition-metal-free trans-selective semireduction of alkynes with pinacolborane and catalytic potassium tert-butoxide. A variety of 3-substituted primary and secondary propiolamides, including an analog of FK866, a potent nicotinamide mononucleotide adenyltransferase (NMNAT) inhibitor, are reduced to the corresponding (E)-3-substituted acrylamide derivatives in up to 99% yield with >99:1 E/Z selectivity. Mechanistic studies suggest that an activated Lewis acid-base complex transfers a hydride to the α-carbon followed by rapid protonation in a trans fashion.
The triflic acid-mediated cyclisation of N-benzyl-cinnamamides
King, Frank D.,Caddick, Stephen
, p. 487 - 491 (2013/07/27)
N-Benzyl-cinnamamides cyclise with triflic acid to form 5-aryl-benzazepinones and/or cinnamamides.
An Unusual Ring-Cleavage of 2,4-Di-N-methylcarbamoylcyclohexanones into Glutaconimide and Cinnamamides
Sadanandam, Yennu S.,Leelavathi, Panaganti,Ansari, Imtiaz A.
, p. 1147 - 1158 (2007/10/02)
3-Aryl-5-hydroxy-5-methyl-2,4-di-N-methylcarbamoylcyclohexanones (1a-h) under acidic and basic conditions underwent ring-cleavage to give 1,4-dimethylglutaconimide (3) and substituted N-methylcinnamamides (4a-h).The probable mechanism for the formation of
