• 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

二氧化硒介导芳基乙二醛与仲胺合成α-酮酰胺

Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines.

作者信息

Shaw Arthur Y, Denning Christine R, Hulme Christopher

机构信息

Department of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA.

出版信息

Tetrahedron Lett. 2012 Aug 8;53(32):4151-4153. doi: 10.1016/j.tetlet.2012.05.136. Epub 2012 Jun 6.

DOI:10.1016/j.tetlet.2012.05.136
PMID:23180891
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3501738/
Abstract

A facile and expeditious synthetic approach to α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals with cyclic and acyclic secondary amines.

摘要

本文描述了一种简便快捷的合成α-酮酰胺3的方法。通过二氧化硒介导的芳基乙二醛1与仲胺2之间的氧化酰胺化反应，在微波辐射的加速作用下，合成了一系列α-酮酰胺3。我们的研究结果表明，诸如哌嗪和哌啶等受限胺在该转化反应中表现出更高的转化率。通过用环状和非环状仲胺从各种芳基乙二醛合成一系列α-酮酰胺3，对该反应进行了探索。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d674/3501738/deade0999cb4/nihms389517f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d674/3501738/577571d0dac3/nihms389517f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d674/3501738/deade0999cb4/nihms389517f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d674/3501738/577571d0dac3/nihms389517f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d674/3501738/deade0999cb4/nihms389517f2.jpg

相似文献

1
Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines.二氧化硒介导芳基乙二醛与仲胺合成α-酮酰胺
Tetrahedron Lett. 2012 Aug 8;53(32):4151-4153. doi: 10.1016/j.tetlet.2012.05.136. Epub 2012 Jun 6.
2
Iodine-TBHP mediated efficient synthesis of α-ketoamides from vinyl azides and amines under mild conditions.碘-过氧化叔丁醇介导的温和条件下乙烯基叠氮化物和胺的α-酮酰胺的高效合成。
Org Biomol Chem. 2022 May 18;20(19):3907-3912. doi: 10.1039/d2ob00458e.
3
Synthesis of aliphatic α-ketoamides from α-substituted methyl ketones a Cu-catalyzed aerobic oxidative amidation.α-取代甲基酮的铜催化有氧氧化酰胺化合成脂肪族 α-酮酰胺。
Org Biomol Chem. 2021 May 19;19(19):4320-4326. doi: 10.1039/d1ob00129a.
4
Ru(II)-catalyzed oxidative coupling of sulfoxonium ylides with amines: efficient synthesis of α-ketoamides and indolo[2,1-]isoquinolines.钌（II）催化的氧化锍叶立德与胺的偶联反应：α-酮酰胺和吲哚并[2,1 -]异喹啉的高效合成
Org Biomol Chem. 2023 Apr 12;21(15):3235-3244. doi: 10.1039/d3ob00187c.
5
Metal-free oxidative amidation of 2-oxoaldehydes: a facile access to α-ketoamides.无金属促进的 2-氧代醛的氧化酰胺化反应：一种α-酮酰胺的简便合成方法。
Org Lett. 2014 Feb 21;16(4):1152-5. doi: 10.1021/ol5000204. Epub 2014 Feb 3.
6
One pot synthesis of α-ketoamides from ethylarenes and amines: a metal free difunctionalization strategy.从乙苯和胺类化合物一锅法合成α-酮酰胺：一种无金属双官能化策略。
Org Biomol Chem. 2016 Dec 28;14(48):11446-11453. doi: 10.1039/c6ob02361d. Epub 2016 Nov 23.
7
Recent Developments in General Methodologies for the Synthesis of α-Ketoamides.α-酮酰胺合成通用方法的最新进展
Chem Rev. 2016 Mar 9;116(5):3241-305. doi: 10.1021/acs.chemrev.5b00443. Epub 2016 Feb 16.
8
Cu-Catalysed oxidative amidation of cinnamic acids/arylacetic acids with 2° amines: an efficient synthesis of α-ketoamides.铜催化肉桂酸/芳基乙酸与仲胺的氧化酰胺化反应：α-酮酰胺的高效合成。
Org Biomol Chem. 2019 Oct 30;17(42):9348-9351. doi: 10.1039/c9ob02045d.
9
Selective Synthesis of -[1,3,5]Triazinyl-α-Ketoamides and -[1,3,5]Triazinyl-Amides from the Reactions of 2-Amine-[1,3,5]Triazines with Ketones.从 2-氨基-[1,3,5]三嗪与酮的反应中选择性合成 -[1,3,5]三嗪基-α-酮酰胺和 -[1,3,5]三嗪基酰胺。
Molecules. 2023 May 25;28(11):4338. doi: 10.3390/molecules28114338.
10
Ligand-Free Pd-Catalyzed Double Carbonylation of Aryl Iodides with Amines to α-Ketoamides under Atmospheric Pressure of Carbon Monoxide and at Room Temperature.在一氧化碳常压和室温下，无配体钯催化芳基碘化物与胺进行双羰基化反应合成α-酮酰胺
J Org Chem. 2015 Aug 7;80(15):7816-23. doi: 10.1021/acs.joc.5b01249. Epub 2015 Jul 13.

引用本文的文献

1
Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles.Aza-Riley 氧化 Ugi-叠氮化物和 Ugi-3CR 产物生成偕三羰基酰胺：两步 MCR-氧化方法学，用于构建功能化的α,β-二酮酰胺和α,β-二酮四唑。
Org Lett. 2018 Mar 2;20(5):1275-1278. doi: 10.1021/acs.orglett.7b03977. Epub 2018 Feb 21.
2
Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents.二氧化硒和有机硒化合物作为氧供体和氧转移剂的合成应用进展
Molecules. 2015 Jun 3;20(6):10205-43. doi: 10.3390/molecules200610205.
3

本文引用的文献

1
Trifluoromethylphenyl as P2 for ketoamide-based cathepsin S inhibitors.三氟甲基苯基作为酮酰胺类组织蛋白酶 S 抑制剂的 P2 部分。
Bioorg Med Chem Lett. 2010 Dec 1;20(23):6890-4. doi: 10.1016/j.bmcl.2010.10.012. Epub 2010 Oct 26.
2
Optimization of alpha-ketoamide based p38 inhibitors through modifications to the region that binds to the allosteric site.通过修饰与别构位点结合的区域来优化基于 α-酮酰胺的 p38 抑制剂。
Bioorg Med Chem Lett. 2010 Aug 15;20(16):4819-24. doi: 10.1016/j.bmcl.2010.06.102.
3
Potent ketoamide inhibitors of HCV NS3 protease derived from quaternized P1 groups.
Synthesis of isocoumarins with different substituted patterns via Passerini-aldol sequence.
通过Passerini-羟醛反应序列合成具有不同取代模式的异香豆素。
Org Lett. 2014 Sep 5;16(17):4504-7. doi: 10.1021/ol502048e. Epub 2014 Aug 20.
源自季铵化 P1 基团的 HCV NS3 蛋白酶强效酮酰胺抑制剂。
Bioorg Med Chem Lett. 2010 Apr 1;20(7):2151-5. doi: 10.1016/j.bmcl.2010.02.051. Epub 2010 Feb 14.
4
Structure-activity relationship of 2-oxoamide inhibition of group IVA cytosolic phospholipase A2 and group V secreted phospholipase A2.2-氧代酰胺对IVA组胞质磷脂酶A2和V组分泌型磷脂酶A2抑制作用的构效关系
J Med Chem. 2007 Aug 23;50(17):4222-35. doi: 10.1021/jm0613673. Epub 2007 Aug 2.
5
Peptidyl-prolyl isomerase inhibitors.肽基脯氨酰异构酶抑制剂
Biopolymers. 2006;84(2):125-46. doi: 10.1002/bip.20240.
6
Synthesis of alpha-ketoamides from a carbamoylsilane and acid chlorides.由氨基甲酰硅烷和酰氯合成α-酮酰胺。
J Org Chem. 2004 Aug 6;69(16):5509-11. doi: 10.1021/jo040164o.
7
Inhibition of group IVA cytosolic phospholipase A2 by novel 2-oxoamides in vitro, in cells, and in vivo.新型2-氧代酰胺在体外、细胞内和体内对IVA组胞质磷脂酶A2的抑制作用。
J Med Chem. 2004 Jul 1;47(14):3615-28. doi: 10.1021/jm030485c.
8
Reactions of a carbamoylstannane with acid chlorides: highly efficient synthesis of alpha-oxo amides.氨基甲酰基锡烷与酰氯的反应：α-氧代酰胺的高效合成
J Org Chem. 2004 Feb 6;69(3):974-6. doi: 10.1021/jo035572r.
9
Cysteine Proteases and Their Inhibitors.半胱氨酸蛋白酶及其抑制剂
Chem Rev. 1997 Feb 5;97(1):133-172. doi: 10.1021/cr950025u.
10
Synthetic routes and lipase-inhibiting activity of long-chain alpha-keto amides.长链α-酮酰胺的合成路线及脂肪酶抑制活性
Lipids. 2001 May;36(5):535-42. doi: 10.1007/s11745-001-0754-0.