酸催化一锅法合成多芳环稠合[3.3.1]二氧杂壬烷衍生物  

One-pot synthesis of multi-aromatic ring-fused[3.3.1] bicyclic compounds via acid-catalyzed

作　　者：吴沁 王爽 王灼钰 黄顺桃 黄超 WU Qin;WANG Shuang;WANG Zhuo-yu;HUANG Shun-tao;HUANG Chao(School of Chemistry and Environment,National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials,Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province,Yunnan Minzu University,Kunming 650503,Yunnan,China)

机构地区：[1]云南民族大学化学与环境学院,生物基材料绿色制备技术国家地方联合工程研究中心,云南省高校智能超分子化学重点实验室,云南昆明650503

出　　处：《云南大学学报（自然科学版）》2022年第5期1027-1033,共7页Journal of Yunnan University(Natural Sciences Edition)

基　　金：国家自然科学基金(21662046,21202142);云南省教育厅科学研究基金(2021Y667);云南省万人计划青年拔尖人才项目。

摘　　要：报道了酸催化一锅法高效合成多芳环稠合[3.3.1]二氧杂壬烷衍生物的方法.以2-羟基查尔酮化合物与2-萘酚为原料反应生成多环稠合氧杂环化合物,其反应机理有别于传统的迈克尔加成引起的环化过程,是酸催化2-羟基查尔酮脱水形成花青素中间体,再与2-萘酚发生亲电取代/分子内加成环化生成多环稠合氧杂环化合物的过程.该反应原子经济性高,后处理简单.以75%~92%产率生成多芳环稠合[3.3.1]二氧杂壬烷化合物,均经过^(1)H NMR、^(13)C NMR、HRMS和IR的表征鉴定.This paper reports an acid-catalyzed tandem cyclization reaction for one-pot efficiently synthesize multi-aromatic ring-fused[3.3.1]dioxazonane compounds.This method used 2-hydroxychalcone compounds and 2-naphtholas as raw materials to synthesize polycyclic O-heterocyclic compounds.The reaction mechanism is different from the tandem process caused by the traditional Michael addition.It is a process in which 2-hydroxychalcone is dehydrated by acid to form anthocyanin intermediates,and then electrophilic substitution/intramolecular addition cyclization with 2-naphthol to form polycyclic fused oxygen-heterocyclic compounds.The reaction atom economy is high,and the post-processing is simple.This method can obtain molecular diversity multi-aromatic ring-fused[3.3.1]dioxazonane compounds with a yield of 75%−92%,all of which were cha-racterized and identified by^(1)H NMR,^(13)C NMR,HRMS and IR.

关 键 词：酸催化 串联环化反应 花青素中间体 多芳环稠合[3.3.1]二氧杂壬烷衍生物 

分 类 号：O621.3[理学—有机化学]