• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

一种从伯胺制备β-芳基氨基醇的高效且原子经济的途径。

An efficient and atom-economical route to -aryl amino alcohols from primary amines.

作者信息

Xiao Zhen, Li Juanjuan, Yue Qiang, Zhang Qian, Li Dong

机构信息

School of Materials and Chemical Engineering, Hubei University of Technology Wuhan 430068 China

Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology Jingmen 448000 China.

出版信息

RSC Adv. 2018 Oct 5;8(60):34304-34308. doi: 10.1039/c8ra07355d. eCollection 2018 Oct 4.

DOI:10.1039/c8ra07355d
PMID:35548644
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9086943/
Abstract

In this paper we reported a novel method for generation of -aryl amino alcohols from ,-disubstituted picolinamides through reduction/ring-opening reaction with NaBH. The ,-disubstituted picolinamides can be easily obtained from primary amines after convenient condensation with picolinic acid and coupling with cyclic ethers. The whole route proceeded under simple and mild conditions with high efficiency. Picolinic acid can be recovered in the form of piconol after reaction. It indicated an efficient and atom-economical route for the preparation of -aryl amino alcohols from primary amines.

摘要

在本文中,我们报道了一种通过与硼氢化钠进行还原/开环反应,从α,β-二取代吡啶酰胺生成α-芳基氨基醇的新方法。α,β-二取代吡啶酰胺可通过伯胺与吡啶甲酸方便地缩合并与环醚偶联后轻松获得。整个路线在简单温和的条件下高效进行。反应后吡啶甲酸可以皮考诺醇的形式回收。这表明从伯胺制备α-芳基氨基醇是一条高效且原子经济的路线。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/b5655c8971a4/c8ra07355d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/f522f9cb51aa/c8ra07355d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/bcd03fb1e39e/c8ra07355d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/b5655c8971a4/c8ra07355d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/f522f9cb51aa/c8ra07355d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/bcd03fb1e39e/c8ra07355d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1505/9086943/b5655c8971a4/c8ra07355d-s3.jpg

相似文献

1
An efficient and atom-economical route to -aryl amino alcohols from primary amines.一种从伯胺制备β-芳基氨基醇的高效且原子经济的途径。
RSC Adv. 2018 Oct 5;8(60):34304-34308. doi: 10.1039/c8ra07355d. eCollection 2018 Oct 4.
2
A New Alkylation of Aryl Alcohols by Boron Trifluoride Etherate.三氟化硼乙醚对芳醇的新型烷基化反应。
Molecules. 2019 Oct 16;24(20):3720. doi: 10.3390/molecules24203720.
3
Regioselective and Stereodivergent Synthesis of Enantiomerically Pure -Diamines from Chiral β-Amino Alcohols with 2-Pyridyl and 6-(2,2'-Bipyridyl) Moieties.手性β-氨基醇的 2-吡啶基和 6-(2,2'-联吡啶)部分的区域和立体选择性合成对映体纯的 -二胺。
Molecules. 2020 Feb 7;25(3):727. doi: 10.3390/molecules25030727.
4
Chiral Arylated Amines via C-N Coupling of Chiral Amines with Aryl Bromides Promoted by Light.通过光促进手性胺与芳基溴的C-N偶联制备手性芳基化胺
Angew Chem Int Ed Engl. 2021 Sep 20;60(39):21536-21542. doi: 10.1002/anie.202108587. Epub 2021 Aug 20.
5
Metal-Free Synthesis of N-Aryl Amides using Organocatalytic Ring-Opening Aminolysis of Lactones.利用内酯的有机催化开环氨解反应无金属合成N-芳基酰胺
ChemSusChem. 2017 May 9;10(9):1969-1975. doi: 10.1002/cssc.201700415. Epub 2017 Apr 13.
6
Efficient methods for the preparation of alkyl-aryl and symmetrical or unsymmetrical dialkyl ethers between alcohols and phenols or two alcohols by oxidation-reduction condensation.通过氧化还原缩合在醇与酚之间或两种醇之间制备烷基芳基醚以及对称或不对称二烷基醚的有效方法。
J Am Chem Soc. 2004 Jun 16;126(23):7359-67. doi: 10.1021/ja0487877.
7
A convenient and efficient route for the allylation of aromatic amines and alpha-aryl aldehydes with alkynes in the presence of a Pd(0)/PhCOOH combined catalyst system.在Pd(0)/苯甲酸组合催化剂体系存在下,实现芳香胺和α-芳基醛与炔烃烯丙基化反应的一种便捷高效的途径。
J Org Chem. 2004 Dec 10;69(25):8745-50. doi: 10.1021/jo0485684.
8
Visible Light Photocatalytic Radical-Radical Cross-Coupling Reactions of Amines and Carbonyls: A Route to 1,2-Amino Alcohols.可见的光催化自由基-自由基交叉偶联反应的胺和羰基化合物:一种途径 1,2-氨基醇。
J Org Chem. 2016 Aug 19;81(16):7237-43. doi: 10.1021/acs.joc.6b01217. Epub 2016 Jul 20.
9
Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.铜/氨基酸催化的芳基卤化物和乙烯基卤化物与亲核试剂的交叉偶联反应。
Acc Chem Res. 2008 Nov 18;41(11):1450-60. doi: 10.1021/ar8000298.
10
An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis.通过过渡金属催化实现原子经济性的 N-芳基和 N-烷基吡咯啉合成方法。
Org Biomol Chem. 2011 Apr 7;9(7):2548-54. doi: 10.1039/c0ob00383b. Epub 2011 Feb 22.

本文引用的文献

1
Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane.三苯基硼催化的叔酰胺的选择性还原胺化反应。
Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13326-13329. doi: 10.1002/anie.201605236.
2
Metal-free reduction of secondary and tertiary N-phenyl amides by tris(pentafluorophenyl)boron-catalyzed hydrosilylation.通过三(五氟苯基)硼催化的硅氢化反应对仲和叔N-苯基酰胺进行无金属还原。
J Org Chem. 2014 Aug 15;79(16):7728-33. doi: 10.1021/jo501299j. Epub 2014 Jul 28.
3
Facile and efficient KOH-catalysed reduction of esters and tertiary amides.
KOH 催化酯和叔酰胺的还原反应,条件温和、效率高。
Chem Commun (Camb). 2013 Oct 28;49(84):9758-60. doi: 10.1039/c3cc45930f.
4
A highly active catalyst for the hydrogenation of amides to alcohols and amines.一种用于将酰胺氢化为醇和胺的高活性催化剂。
Angew Chem Int Ed Engl. 2011 Oct 24;50(44):10377-80. doi: 10.1002/anie.201103137. Epub 2011 Aug 26.
5
Microwave-assisted solventless reaction of iridium-catalyzed alkylation of amines with alcohols in the absence of base.微波辅助无溶剂反应:铱催化的胺与醇的烷基化反应,无需碱存在。
Org Lett. 2011 Oct 7;13(19):5386-9. doi: 10.1021/ol202281h. Epub 2011 Sep 12.
6
Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand.定义明确的 Cp*Ru 配合物在质子化胺配体存在下催化酰胺和酯的氢化反应。
J Am Chem Soc. 2011 Mar 30;133(12):4240-2. doi: 10.1021/ja1117254. Epub 2011 Mar 7.
7
Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues.钙受体拮抗剂I. 基于氨基醇的甲状旁腺激素促分泌剂。
J Med Chem. 2009 Jul 9;52(13):3982-93. doi: 10.1021/jm900364m.
8
Enantioselective henry reactions under dual Lewis acid/amine catalysis using chiral amino alcohol ligands.使用手性氨基醇配体在双路易斯酸/胺催化下的对映选择性亨利反应。
Angew Chem Int Ed Engl. 2005 Jun 20;44(25):3881-4. doi: 10.1002/anie.200463075.
9
Investigation into the structure-activity relationship of novel concentration dependent, dual action T-type calcium channel agonists/antagonists.新型浓度依赖性双作用T型钙通道激动剂/拮抗剂的构效关系研究
Bioorg Med Chem. 2005 Jun 1;13(11):3821-39. doi: 10.1016/j.bmc.2005.03.004.
10
The atom economy--a search for synthetic efficiency.原子经济性——对合成效率的探索。
Science. 1991 Dec 6;254(5037):1471-7. doi: 10.1126/science.1962206.