Transformations of N,N-disubstituted 2-aminocyclopentanones on Pd catalyst

Captodative aminoalkenes

“…Analogously, the reactions of methyl 4-nitrophenylpropiolate (50) with some secondary amines afforded the corresponding a-amino derivatives 51. 153 In the synthesis of pyrimidine derivatives from triazines and 1-diethylaminoprop-1-yne (52), HCN, which was eliminated in the course of the reaction, added to the starting alkyne to produce 2-diethylaminocrotononitrile (53) in yields of up to 76%. 154 Cyclic a,a H -dibromoketones 54a ± c reacted with primary 155 and secondary amines 17,156 to give either Favorskii rearrangement products 55b,c or the corresponding 2-aminocycloalk-2enones 56a ± c depending on the ring size of the ketone and the structure of the nucleophile.…”

“…Thus 2-aminocyclopent-2-enones were obtained in high yields by passing gaseous 2-aminocyclopentanones over Pd/C. 53…”