64330-10-5Relevant academic research and scientific papers
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.
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
