Highly selective synthesis of functionalized morphan derivatives through a multi-component cascade reaction of 3-formylchromones, 2-naphthols, and enaminones  

作　　者：Xinling Cao Yinggang Duan Kaihong Lv Zihan Lu Yihua Chen Shengjiao Yan 

机构地区：[1]Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University),Ministry of Education,School of Chemical Science and Technology,Yunnan University,Kunming 650091,China

出　　处：《Green Synthesis and Catalysis》2023年第4期321-329,共9页绿色合成与催化（英文）

基　　金：We are grateful for financial support from the Natural Science Foundation of Yunnan Province,China(No.2019FY003003);the Scientific and Technological Innovation Team of Green Synthesis and Activity Research of Natural-like Heterocyclic Compound Libraries in Universities of Yunnan Province(No.C17624011121).The authors thank the Advanced Analysis and Measurement Center of Yunnan University for the sample testing service.

摘　　要：A novel protocol for the preparation of highly functionalized 2-azabicyclo[3.3.1]nonane(morphan)derivatives via a multicomponent cascade reaction,involving 3-formylchromones,2-naphthols,and enaminones in the ionic liquid[BMIM]PF6 as the solvent and promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU),was developed,which involved the cleavage of one C–O bond and formation of four bonds(1 C–O,1 C–N,and 2 C–C bonds).As a result,a series of morphan derivatives were produced through a cascade reaction,including a sequence of 1,2-addition,enol-keto tautomerization,Michael addition,dehydration,another Michael addition,imine-enamine tautomerization,and N-alkylation reactions,which were accompanied by a ring-opening reaction.This protocol was suitable for combinatorial and parallel syntheses of natural product-like morphan compounds in a one-pot reaction rather than through tedious multi-step reactions.

关 键 词：Morphan derivatives Site-selective synthesis Cascade reaction ENAMINONES 3-Formylchromones 

分 类 号：O62[理学—有机化学]