烯丙基硫叶立德参与的串联环化反应合成苯并吡喃衍生物  

Synthesis of Benzopyran Derivatives via The Allylic Sulfur Ylide Mediated Tandem Annulations

作　　者：戴青松 杨四琳[2] 何美浩 刘宇 刘万聪[2] 王亚鹏 郭钊宜 张翔 王启卫 DAI Qingsong;YANG Silin;HE Meihao;LIU Yu;LIU Wancong;WANG Yapeng;GUO Zhaoyi;ZHANG Xiang;WANG Qiwei(Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China;University of Chinese Academy of Sciences, Beijing 100049, China;School of Science, Xihua University, Chengdu 610039, China)

机构地区：[1]中国科学院成都有机化学研究所,四川成都610041 [2]成都大学药学院(川抗所)抗生素研究与再评价四川省重点实验室,四川成都610106 [3]中国科学院大学,北京100491 [4]西华大学理学院,四川成都610039

出　　处：《合成化学》2022年第5期356-364,共9页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21871031,22071011);西华大学人才引进项目(Z202084)。

摘　　要：以酯基烯丙基锍盐作为起始原料,在碱的作用下,与醌亚胺类化合物经氧杂[3+3]串联环化反应,以中等收率合成了一系列苯并吡喃衍生物。并进一步以对氨基(羟基)酚类化合物为底物,经原位氧化串联氧杂[3+3]环化反应,通过“一锅法”更为高效的实现了目标骨架的构建。代表产物的结构经X-ray单晶衍射确证,所有化合物的结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征。In the presence of base,a series of benzopyran derivatives were facilely synthesized in medium yields via the allylic sulfur ylides mediated oxa-[3+3]tandem annulation with quinone imines,using crotonate-derived sulfonium salts as starting materials.Furthermore,using the p-amino-(hydroxyl)phenol as substrates,the target skeleton was constructed more efficiently through“one-pot”synthesis via in-situ oxidation tandem oxa-[3+3]annulation.The structure of the representative example was confirmed by X-ray ananlysis,and the obtained compounds were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).

关 键 词：烯丙基硫叶立德 醌亚胺 氧杂[3+3]环化反应 苯并吡喃衍生物 一锅法 合成 

分 类 号：O62[理学—有机化学]