1690-76-2Relevant articles and documents
EFFICIENT SYNTHESIS OF N-SUBSTITUTED LACTAMS FROM (N-ARYLSULFONYLOXY)AMINES AND CYCLIC KETONES
Hoffman, Robert V.,Salvador, James M.
, p. 4207 - 4210 (1989)
A new method is reported for the direct preparation of N-substituted lactams from cycloalkanones.N-(p-nitrobenzenesulfonoxyl) methylamine 1a (CH3NH-OSO2C6H4NO2) was reacted with a series of cycloalkanones to give good yields of N-methyl lactams.An addition-rearrangement pathway accounts for the ring-expanded lactam products.A series of N-alkyl-N-arylsulfonoxyl amines were generated in situ and reacted with cyclobutanone to give N-alkyl pyrrolidinones in high yields.
Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3)?H Olefination
Park, Hojoon,Li, Yang,Yu, Jin-Quan
supporting information, p. 11424 - 11428 (2019/07/17)
PdII-catalyzed C(sp3)?H olefination of weakly coordinating native amides is reported. Three major drawbacks of previous C(sp3)?H olefination protocols, 1) in situ cyclization of products, 2) incompatibility with α-H-containing substrates, and 3) installation of exogenous directing groups, are addressed by harnessing the carbonyl coordination ability of amides to direct C(sp3)?H activation. The method enables direct C(sp3)?H functionalization of a wide range of native amide substrates, including secondary, tertiary, and cyclic amides, for the first time. The utility of this process is demonstrated by diverse transformations of the olefination products.
PHOTOCYCLIZATION OF ENAMIDES. 38 REDUCTIVE PHOTOCYCLIZATION OF α-(METHYLTHIO)- AND α-(ARYLTHIO)ENAMIDES
Naito, Takeaki,Tanada, Hiromi,Suzuki, Yumiko,Saito, Haruko,Kiguchi, Toshiko,Ninomiya, Ichiya
, p. 2345 - 2366 (2007/10/02)
Reductive photocyclization of α-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of α-(arylthio)enamides (6) and (12) was found to afford five-membered lactams (7) and (13) as major products.A novel total s