Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols

Jianwei Yan; Tianjun Ni; Fulin Yan

首页> 外文期刊>RSC Advances >Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols

【24h】

Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols

机译：Friedel-Crafts吲哚与邻羰基化合物的吲哚反应，原位原位产生1,3-二羰基化合物和速度：高度选择性合成叔醇

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

A novel Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds, which produces indole substituted tertiary alcohols in good to excellent yields and with good functional group tolerance, has been developed. The mechanistic pathway for this process involves the initial disproportionation of TEMPO, a-oxyamination of the 1,3-dicarbonyl compound followed by N-O bond cleavage to form the tricarbonyl intermediate. Addition of indole to this intermediate then generates the tertiary alcohol product. This method can also be used for the synthesis of pyrrole-containing tertiary alcohols. Further efforts aimed at elucidating the mechanism of the reaction and boardening the substrate scope of this process are ongoing.

机译：已经开发出一种新的吲哚-Craft吲哚的反应，其原位从1,3-二羰基化合物产生的吲哚代取代的叔醇与优异的产率和良好的官能团耐受性。该方法的机械途径涉及Tempo的初始歧化，1,3-二羰基化合物的A-氧基，然后进行N-O键裂解以形成三羰基中间体。向该中间体添加吲哚然后产生叔醇产物。该方法还可用于合成含吡咯的叔醇。旨在阐明反应和起水量的底物范围的进一步努力正在进行中。

著录项

来源
《RSC Advances》 |2015年第109期|共5页
作者
Jianwei Yan; Tianjun Ni; Fulin Yan;
展开▼
作者单位

School of Pharmacy Xinxiang Medical University Xinxiang Henan 453003 P. R. China.;

Department of Chemistry Xinxiang Medical University Xinxiang Henan 453003 P. R. China;

School of Pharmacy Xinxiang Medical University Xinxiang Henan 453003 P. R. China.;

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类化学;
关键词

相似文献

外文文献
中文文献
专利

1. Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols [J] . Jianwei Yan, Tianjun Ni, Fulin Yan RSC Advances . 2015,第109期

机译：Friedel-Crafts吲哚与邻羰基化合物的吲哚反应，原位原位产生1,3-二羰基化合物和速度：高度选择性合成叔醇
2. Indium(III) Chloride-Catalyzed Propargylation/Amination/Cyclo- isomerization Tandem Reaction: One-Pot Synthesis of Highly Substituted Pyrroles from Propargylic Alcohols, 1,3-Dicarbonyl Compounds and Primary Amines [J] . Xiao-tao Liu, Lei Huang, Fei-jian Zheng Advanced synthesis & catalysis . 2008,第17期

机译：氯化铟（III）催化的丙炔化/胺化/环异构化串联反应：由丙炔醇，1,3-二羰基化合物和伯胺一锅合成高取代的吡咯
3. Gold(III)-catalyzed tandem reaction of O-arylhydroxylamines with 1,3-dicarbonyl compounds: Highly selective synthesis of 3-carbonylated benzofuran derivatives [J] . Liu Y., Qian J., Lou S., The Journal of Organic Chemistry . 2010,第18期

机译：金（III）催化的O-芳基羟胺与1,3-二羰基化合物的串联反应：3-羰基化苯并呋喃衍生物的高度选择性合成
4. A one-pot synthesis of functionalized 1,3-thiazoles from thioamides and 2-chloro-1,3-dicarbonyl compounds in an ionic liquid [C] . Issa Yavari, S. Zahra Sayyed-Alangi, Rahimeh Hajinasiri European Symposium on Organic Chemistry . 2009

机译：离子液体中硫胺和2-氯-1,3-二羰基化合物的官能化1,3-噻唑的单罐合成
5. Vicinal tricarbonyl compounds: Applications in alkaloid synthesis [D] . van Duzer, John Henry 1990

机译：邻三羰基化合物：在生物碱合成中的应用
6. Three-Component Cascade Reaction of 11-Enediamines NN-Dimethylformamide Dimethyl Acetaland 13-Dicarbonyl Compounds: Selective Synthesis of Diverse 2-AminopyridineDerivatives [O] . Quan-Xing Zi, Sheng-Jiao Yan, *, 2019

机译：11-烯二胺NN-二甲基甲酰胺二甲基乙缩醛的三组分级联反应和13-二羰基化合物：各种2-氨基吡啶的选择性合成衍生品
7. InCl3 Catalyzed One-Pot Synthesis of Highly Substituted Pyrroles from Propargylic Alcohols, 1,3-Dicarbonyl Compounds and Primary Amines and Synthesis of 2'-Deoxy-β-L-thymidine and C24H30 as Precursor to C24, C24H12 Fullerene [O] . 黄磊 2009

机译：InCl3催化由炔丙基醇，1,3-二羰基化合物和伯胺合成高取代吡咯并合成2'-脱氧-β-L-胸苷和C24H30作为C24，C24H12富勒烯的前体
8. Mild and Highly Selective Ultrasound-Promoted Zinc/Acetic Acid Reduction of C = CBonds in alpha, Beta-Unsaturated gamma-Dicarbonyl Compounds [R] . Marchand, A. P., Reddy, M. 1991

机译：轻度和高度选择性超声促进锌/乙酸还原C，在α，β-不饱和γ-二羰基化合物中的CBonds

Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols

摘要

著录项

相似文献

相关主题

期刊订阅