2-芳基苯酚的形式脱芳构化氢胺化反应
Formal Dearomative Hydroamination of 2-Arylphenols.
作者信息
Wiley Robert E, Eng Michael C, Clarkson Aidan J, Johnson Jeffrey S
机构信息
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
出版信息
J Org Chem. 2025 Jan 10;90(1):913-918. doi: 10.1021/acs.joc.4c02654. Epub 2024 Dec 20.
Abstract
An acid-promoted dearomative rearrangement of -arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of -aminoalcohols on a cyclohexadiene core. This method serves as an efficient entry to the pharmaceutically relevant 1-arylcyclohexylamine scaffold in two steps (one purification) from commercially available or readily prepared 2-arylphenols.
摘要
芳基羟胺的酸促进去芳构化重排反应可生成2-氨基环己二烯-1-酮，进而可将其还原淬灭，用于在环己二烯核心上合成氨基醇。该方法从市售或易于制备的2-芳基苯酚出发，通过两步反应（一步纯化），为药学相关的1-芳基环己胺骨架提供了一条有效的合成途径。
相似文献
1
Formal Dearomative Hydroamination of 2-Arylphenols.2-芳基苯酚的形式脱芳构化氢胺化反应
J Org Chem. 2025 Jan 10;90(1):913-918. doi: 10.1021/acs.joc.4c02654. Epub 2024 Dec 20.
2
Copper-Catalyzed Dearomative 1,2-Hydroamination.铜催化的去芳构化1,2-氢胺化反应
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202407281. doi: 10.1002/anie.202407281. Epub 2024 Jul 16.
3
Construction of Indoline/Indolenine Ring Systems by a Palladium-Catalyzed Intramolecular Dearomative Heck Reaction and the Subsequent Aza-semipinacol Rearrangement.钯催化的分子内去芳构化 Heck 反应和随后的氮杂-semi 邻二醇重排构建吲哚啉/吲哚啉环系统。
J Org Chem. 2021 Apr 16;86(8):5727-5743. doi: 10.1021/acs.joc.1c00209. Epub 2021 Mar 31.
4
Dearomative hydroamination of heteroarenes catalyzed by the phenolate photocatalyst.酚盐光催化剂催化杂芳烃的脱芳构化氢胺化反应
Chem Commun (Camb). 2024 Nov 5;60(89):13083-13086. doi: 10.1039/d4cc03879g.
5
Dearomative [2 + 2] Cycloaddition and Formal C-H Insertion Reaction of o-Carboryne with Indoles: Synthesis of Carborane-Functionalized Heterocycles.去芳构化[2 + 2]环加成和 o-碳硼烷与吲哚的形式 C-H 插入反应：碳硼烷功能化杂环的合成。
J Am Chem Soc. 2015 Jul 29;137(29):9423-8. doi: 10.1021/jacs.5b05426. Epub 2015 Jul 20.
6
CuI-mediated sequential iodination/cycloetherification of o-arylphenols: synthesis of 2- or 4-iododibenzofurans and mechanistic studies.CuI 介导的邻芳基苯酚的顺序碘化/环醚化反应：2-或 4-碘二苯并呋喃的合成及机理研究。
Org Lett. 2012 Oct 19;14(20):5362-5. doi: 10.1021/ol302562a. Epub 2012 Oct 2.
7
Tandem cyclocondensation of 1,3-bis-sulfonylpropan-2-ones with arylaldehydes. One-pot synthesis of tris-sulfonyl 3-arylphenols.1,3-双磺酰基丙烷-2-酮与芳醛的串联环缩合反应。三磺酰基 3-芳基苯酚的一锅合成法。
Org Biomol Chem. 2022 Nov 9;20(43):8471-8483. doi: 10.1039/d2ob01703b.
8
One-pot cascade reactions of 1-arylpenta-3,4-dien-2-ones leading to 2-arylphenols and dibenzopyroanones.1-芳基戊-3,4-二烯-2-酮一锅法串联反应生成2-芳基苯酚和二苯并吡喃酮。
Chem Commun (Camb). 2014 Dec 11;50(95):14968-70. doi: 10.1039/c4cc06204c.
9
Regio- and Enantioselective Synthesis of 1,2-Diamines by Formal Hydroamination of Enamines: Scope, Mechanism, and Asymmetric Synthesis of Orthogonally Protected Bis-Piperazines as a Privileged Scaffold.通过烯胺的形式氢胺化反应实现1,2 - 二胺的区域和对映选择性合成：范围、机理以及作为优势骨架的正交保护双哌嗪的不对称合成
Chemistry. 2024 Mar 15;30(16):e202303078. doi: 10.1002/chem.202303078. Epub 2024 Jan 31.
10
Recent Advances in Dearomative Partial Reduction of Benzenoid Arenes.苯系芳烃去芳构化部分还原的最新进展
Angew Chem Int Ed Engl. 2024 May 21;63(21):e202402819. doi: 10.1002/anie.202402819. Epub 2024 Apr 9.
本文引用的文献
1
Copper-Catalyzed Dearomative 1,2-Hydroamination.铜催化的去芳构化1,2-氢胺化反应
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202407281. doi: 10.1002/anie.202407281. Epub 2024 Jul 16.
2
Catalytic Asymmetric Synthesis of Aza-Quaternary Carbon Cyclohexadieneones Enabled by Aminative Dearomatization of Phenols.通过酚的氮杂去芳构化实现手性氮杂季碳环己二烯酮的催化不对称合成。
Org Lett. 2023 Jun 30;25(25):4740-4744. doi: 10.1021/acs.orglett.3c01746. Epub 2023 Jun 21.
3
Arylcyclohexylamine Derivatives: Pharmacokinetic, Pharmacodynamic, Clinical and Forensic Aspects.芳基环己基胺衍生物：药代动力学、药效学、临床和法医学方面。
Int J Mol Sci. 2022 Dec 8;23(24):15574. doi: 10.3390/ijms232415574.
4
Dearomatization of Cyclic Diphenylhydrazines: Harnessing the -Semidine Rearrangement for the Synthesis of Spirocyclic Tetrahydroquinolines.环状二苯肼的去芳构化：利用 -半二嗪重排反应合成螺环四氢喹啉。
Org Lett. 2022 Nov 4;24(43):8014-8018. doi: 10.1021/acs.orglett.2c03220. Epub 2022 Oct 21.
5
Mechanistic Insight into Phenol Dearomatization by Hypervalent Iodine: Direct Detection of a Phenoxenium Cation.高价碘介导苯酚去芳构化反应的机理探究：苯氧鎓离子的直接检测
J Org Chem. 2022 Nov 4;87(21):14274-14283. doi: 10.1021/acs.joc.2c01765. Epub 2022 Oct 10.
6
Synthesis of (+)-ribostamycin by catalytic, enantioselective hydroamination of benzene.通过苯的催化对映选择性氢胺化反应合成（+）-核糖霉素。
Nat Synth. 2022 Jul;1(7):542-547. doi: 10.1038/s44160-022-00080-x. Epub 2022 May 26.
7
HFIP in Organic Synthesis.六氟异丙醇在有机合成中的应用。
Chem Rev. 2022 Aug 10;122(15):12544-12747. doi: 10.1021/acs.chemrev.1c00749. Epub 2022 Jul 17.
8
Hydroamination of Dihapto-Coordinated Benzene and Diene Complexes of Tungsten: Fundamental Studies and the Synthesis of γ-Lycorane.钨的二配位苯和二烯配合物的氢胺化反应：基础研究及γ-石蒜碱的合成
Helv Chim Acta. 2021 Oct;104(10). doi: 10.1002/hlca.202100103. Epub 2021 Aug 10.
9
Asymmetric Direct/Stepwise Dearomatization Reactions Involving Hypervalent Iodine Reagents.涉及高价碘试剂的不对称直接/逐步去芳构化反应。
Chem Asian J. 2022 Feb 14;17(4):e202101115. doi: 10.1002/asia.202101115. Epub 2021 Dec 7.
10
Asymmetric dearomatization catalysed by chiral Brønsted acids via activation of ynamides.手性 Brønsted 酸通过激活炔酰胺实现不对称去芳构化反应。
Nat Chem. 2021 Nov;13(11):1093-1100. doi: 10.1038/s41557-021-00778-z. Epub 2021 Oct 11.
Zotero 插件