Synthesis Of 6H-chromeno[4,3-b]quinolin-6-one Via Cu?OAc?₂/TBPB System With DMF As Carbon Source

In this dissertation,the first example of the Cu?OAc?₂·H₂O/TBPB system cyclization of 4-anilinocoumarins for synthesis of 6H-chromeno[4,3-b]quinolin-6-ones employing DMF as carbon source is reported.Moreover,synthesis of 3,3'-methylenebis?4-?phenylamino?-2H-chromen-2-one?with AgTFA as catalyst was also studied.This dissertation consisted of four chapters.The first chapter introduced the coumarin compounds and their biological activities.All the synthesis methods of 6H-chromeno[4,3-b] quinolin-6-ones were reviewed as well.The second chapter summarized all the synthesis reactions about DMF as carbon source in recent years.The third chapter proposed the copper-catalyzed cyclization for synthesis of 6H-chromeno[4,3-b]quinolin-6-ones.A series of studies on the catalyst,oxidant,temperature and so on were carried out.Finally,Cu?OAc?₂·H₂O was chose as the catalyst,TBPB as the oxidant and NaHSO3 as the additive.With the optimized reaction conditions in hand,twenty derivatives of 6H-chromeno[4,3-b]quinolin-6-ones were synthetized with moderate to good yields.The structures of 6H-chromeno[4,3-b]quinolin-6-ones were confirmed by ESI,¹H-NMR and ¹³C-NMR.At last,the possible mechanism was proposed and the remained compounds structure were described in detailes.The fourth chapter was focused on a preliminary synthesis of 3,3'-methylenebis?4-?phenylamino?-2H-chromen-2-one?.a lot of the reaction conditions were developed and one compound was synthetized with a moderate yield,which confirmed by HRMS-ESI,¹H-NMR and ¹³C-NMR.The reaction was also metal catalyzed coupling-reaction with DMF as carbon source.