通过与伯醇的催化脱氢偶联进行单瓶合成N-酰化吲哚。
Single-flask synthesis of N-acylated indoles by catalytic dehydrogenative coupling with primary alcohols.
作者信息
Maki Brooks E, Scheidt Karl A
机构信息
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
出版信息
Org Lett. 2009 Apr 2;11(7):1651-4. doi: 10.1021/ol900306v.
Abstract
Indoles and alcohols can be coupled in a dehydrogenative process catalyzed by tetrapropylammonium perruthenate. This efficient approach to indolylamides proceeds in a single flask under mild conditions. By employing substituted indoles and alkyl, branched, or benzylic alcohols, a variety of indolylamides can be formed. Aryl indolylamides can be functionalized through an additional dehydrogenative coupling to furnish elaborated polycyclic heterocycles similar to biologically active structures previously reported.
摘要
吲哚和醇类可以在过钌酸四丙铵催化的脱氢过程中偶联。这种制备吲哚酰胺的有效方法在温和条件下于单口烧瓶中进行。通过使用取代吲哚和烷基、支链或苄醇，可以形成多种吲哚酰胺。芳基吲哚酰胺可以通过额外的脱氢偶联进行官能化，以提供类似于先前报道的生物活性结构的复杂多环杂环化合物。
相似文献
1
Single-flask synthesis of N-acylated indoles by catalytic dehydrogenative coupling with primary alcohols.通过与伯醇的催化脱氢偶联进行单瓶合成N-酰化吲哚。
Org Lett. 2009 Apr 2;11(7):1651-4. doi: 10.1021/ol900306v.
2
Palladium-catalyzed direct C2 arylation of N-substituted indoles with 1-aryltriazenes.钯催化的N-取代吲哚与1-芳基三氮烯的直接C2芳基化反应。
Chem Asian J. 2014 Sep;9(9):2584-9. doi: 10.1002/asia.201402274. Epub 2014 Jun 11.
3
Silver triflate catalyzed tandem heterocyclization/alkynylation of 1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles.三氟甲磺酸银催化的 1-((2-对甲苯磺酰氨基)芳基)丁-2-炔-1,4-二醇的串联杂环化/炔基化反应生成 2-炔基吲哚。
Chemistry. 2012 May 14;18(20):6133-7. doi: 10.1002/chem.201200578. Epub 2012 Apr 18.
4
Palladium-catalyzed synthesis of 3-acylated indoles involving oxidative cross-coupling of indoles with α-amino carbonyl compounds.钯催化的 3 酰化吲哚的合成涉及吲哚与α-氨基羰基化合物的氧化交叉偶联。
J Org Chem. 2013 Nov 15;78(22):11163-71. doi: 10.1021/jo402215s. Epub 2013 Oct 24.
5
Catalytic enantioselective construction of quaternary stereocenters: assembly of key building blocks for the synthesis of biologically active molecules.催化对映选择性构建季碳立体中心：用于合成生物活性分子的关键结构单元的组装
Acc Chem Res. 2015 Mar 17;48(3):740-51. doi: 10.1021/ar5004658. Epub 2015 Feb 25.
6
Palladium-catalyzed aryl amination-heck cyclization cascade: a one-flask approach to 3-substituted indoles.钯催化的芳基胺化-赫克环化串联反应：一种制备3-取代吲哚的单瓶法
Angew Chem Int Ed Engl. 2008;47(5):888-90. doi: 10.1002/anie.200703763.
7
Regioselective synthesis of 4-substituted indoles via C-H activation: a ruthenium catalyzed novel directing group strategy.通过 C-H 活化的 4-取代吲哚的区域选择性合成：一种钌催化的新型导向基团策略。
Org Lett. 2013 Dec 20;15(24):6262-5. doi: 10.1021/ol4031149. Epub 2013 Nov 25.
8
Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis.在温和条件下通过有氧双脱氢催化从醇类中高度实用地合成腈和杂环化合物。
Org Lett. 2013 Apr 19;15(8):1850-3. doi: 10.1021/ol400459y. Epub 2013 Apr 5.
9
Ruthenium-catalyzed self-coupling of primary and secondary alcohols with the liberation of dihydrogen.钌催化的伯醇和仲醇的自身偶联反应，伴随着氢气的释放。
J Org Chem. 2013 Jul 5;78(13):6593-8. doi: 10.1021/jo4008699. Epub 2013 Jun 13.
10
A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols.一种通用且高效的催化剂，用于钯催化芳基卤化物与伯醇的 C-O 偶联反应。
J Am Chem Soc. 2010 Aug 25;132(33):11592-8. doi: 10.1021/ja103248d.
引用本文的文献
1
Convergent Total Synthesis of Erchinines A and B and Their C20 Epimers.海胆素A和B及其C20差向异构体的汇聚式全合成
J Am Chem Soc. 2025 Jul 30;147(30):26769-26775. doi: 10.1021/jacs.5c07636. Epub 2025 Jul 18.
2
The sustainable synthesis of peptidomimetics chemoenzymatic tandem oxidation-Ugi reaction.肽模拟物的可持续合成——化学酶串联氧化-Ugi反应。
RSC Adv. 2018 Aug 8;8(50):28405-28413. doi: 10.1039/c8ra04583f. eCollection 2018 Aug 7.
3
Chemoselective -acylation of indoles using thioesters as acyl source.使用硫酯作为酰基源对吲哚进行化学选择性N-酰化反应。
Beilstein J Org Chem. 2022 Jan 10;18:89-94. doi: 10.3762/bjoc.18.9. eCollection 2022.
4
An Efficient, Eco-friendly and Sustainable One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Directly from Alcohols Catalyzed by Heteropolyanion-Based Ionic Liquids.杂多阴离子基离子液体催化醇直接一锅法高效、环保、可持续合成 3,4-二氢嘧啶-2(1H)-酮。
Molecules. 2017 Sep 11;22(9):1531. doi: 10.3390/molecules22091531.
5
Straightforward protocol for the efficient synthesis of varied N(1)-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up.高效合成多种N(1)-酰化（氮杂）吲哚2-/3-链烷酸及酯的简便方案：优化与放大
Tetrahedron. 2012 Dec 2;68(48):10049-10058. doi: 10.1016/j.tet.2012.08.044.
本文引用的文献
1
N-Heterocyclic Carbene-Catalyzed Oxidations.N-杂环卡宾催化的氧化反应
Tetrahedron. 2009 Apr 18;65(16):3102-3109. doi: 10.1016/j.tet.2008.10.033.
2
Catalyzed dehydrogenative coupling of primary alcohols with water, methanol, or amines.
Angew Chem Int Ed Engl. 2009;48(3):559-63. doi: 10.1002/anie.200804757.
3
Amide synthesis from alcohols and amines by the extrusion of dihydrogen.通过脱出氢气由醇类和胺类合成酰胺。
J Am Chem Soc. 2008 Dec 31;130(52):17672-3. doi: 10.1021/ja808129p.
4
Metal-free one-pot oxidative amidation of aldoses with functionalized amines.醛糖与功能化胺的无金属一锅法氧化酰胺化反应
J Org Chem. 2008 Nov 7;73(21):8647-50. doi: 10.1021/jo801626v. Epub 2008 Oct 8.
5
N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters.N-杂环卡宾催化未活化醛氧化为酯
Org Lett. 2008 Oct 2;10(19):4331-4. doi: 10.1021/ol8018488. Epub 2008 Aug 30.
6
One-pot oxidative esterification and amidation of aldehydes.醛的一锅法氧化酯化和酰胺化反应。
Chemistry. 2008;14(21):6302-15. doi: 10.1002/chem.200800353.
7
N-heterocyclic carbene (NHC)-catalyzed direct amidation of aldehydes with nitroso compounds.N-杂环卡宾（NHC）催化醛与亚硝基化合物的直接酰胺化反应。
Org Lett. 2008 Jun 19;10(12):2333-6. doi: 10.1021/ol8004276. Epub 2008 May 14.
8
Total synthesis of (+/-)-dysibetaine.（±）-去甲甜菜碱的全合成
Org Lett. 2008 Apr 3;10(7):1461-3. doi: 10.1021/ol800245m. Epub 2008 Mar 5.
9
Rh(II)-catalyzed intermolecular oxidative sulfamidation of aldehydes: a mild efficient synthesis of N-sulfonylcarboxamides.铑（II）催化的醛的分子间氧化磺酰胺化反应：N-磺酰基羧酰胺的温和高效合成
J Am Chem Soc. 2007 Nov 21;129(46):14106-7. doi: 10.1021/ja073872a. Epub 2007 Oct 30.
10
N-heterocyclic carbene-catalyzed redox amidations of alpha-functionalized aldehydes with amines.N-杂环卡宾催化α-官能化醛与胺的氧化还原酰胺化反应。
J Am Chem Soc. 2007 Nov 14;129(45):13798-9. doi: 10.1021/ja0768136. Epub 2007 Oct 23.
Zotero 插件