Gold or no gold: one-pot synthesis of tetrahydrobenz[b]azepin-4-ones from tertiary N-(but-3-ynyl)anilines.
Depending on the tertiary aniline substrates, an efficient, one-pot synthesis of tetrahydrobenz[b]azepin-4-ones needs either gold catalysts or no catalyst at all. In the reaction, the aniline nitrogen plays a unique role in relaying "O" from m-CPBA to a tethered C-C triple bond, which is inert to the oxidant under the mild reaction conditions.
Cui
Li
L
Department of Chemistry, University of Nevada, Reno, Nevada 89557, USA.
Zhang
Guozhu
G
Peng
Yu
Y
Zhang
Liming
L
D000480:Alkynes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure
D000480:Alkynes; D000814:Aniline Compounds; D001569:Benzodiazepines; D006046:Gold