Iodine(?)-mediated Novel Construction Of Dibenzoxazepinone Skeleton Through Oxidative C-N Formation

Dibenzoxazepinone skeleton and its derivatives are very important heterocyclic motif which have been found to show many biological activities,such as antidepressant,antitumor,and anti-HIV activities.Besides,they also existed in many important drug intermediates and the compounds which have the biological activites.To date,many methods have been reported to synthesize dibenzoxazepinone skeleton and its derivatives.Although existing methods have their own advantages,some of them require the use of transition metals or harsh conditions.Hypervalent iodine reagents have been widely used to construct C-C,C-N and C-O bonds because of its particular oxidative feature,thus gradually develop a new strategy for the construction of heterocyclic compounds.In this paper,we report an iodine(III)-mediated construction of the dibenzoxazepinone skeleton and its derivatives from 2-(aryloxy)benzamides,which mainly includes the following several aspects:1.According to the literatures,we have designed an iodine(III)-mediated construction of dibenzoxazepinone skeleton from 2-(aryloxy)benzamides.2.After various conditions screening,such as use of different hypervalent iodine reagents,replacement of different solvents,changing the temperature,etc.,we finally found out optimal conditions,and synthesized dibenzoxazepinones with different substituents under this conditions.3.During the process of synthesizing the dibenzoxazepinone with different substituents,we found some 2-aryloxy benzamides could not be converted to the desired products under standard conditions,but all of those products were separated,purified,and further characterized.4.The N-methoxy group of target dibenzoxazepinone skeleton and its derivatives could be removed by using palladium catalyzed hydrogenation reaction.Through this method,we can obtain the dibenzoxazepinone compounds and its derivatives with no substitute on nitrogen atom,thus obtaining the compounds with potential biological activity by introducing different groups to the nitrogen atom.