羧酸与芳炔的分子间 C-O 加成。
Intermolecular C-O addition of carboxylic acids to arynes.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
Org Lett. 2010 Jul 16;12(14):3117-9. doi: 10.1021/ol101017z.
Abstract
A novel, efficient, and expedient route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed starting from readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.
摘要
一种新颖、高效、简便的方法，从易得的羧酸和商业可得的邻-(三甲基甲硅烷基)芳基三氟甲磺酸酯出发，制备了具有生物和药物重要性的邻-羟基芳基酮、黄烷酮、4-色满酮和黄酮。
相似文献
1
Intermolecular C-O addition of carboxylic acids to arynes.羧酸与芳炔的分子间 C-O 加成。
Org Lett. 2010 Jul 16;12(14):3117-9. doi: 10.1021/ol101017z.
2
Intermolecular C-O Addition of Carboxylic Acids to Arynes: Synthesis of -Hydroxyaryl Ketones, Xanthones, 4-Chromanones, and Flavones.羧酸与芳炔的分子间碳-氧加成反应：α-羟基芳基酮、呫吨酮、4-色满酮和黄酮的合成
Tetrahedron. 2013 Apr 1;69(13):2789-2798. doi: 10.1016/j.tet.2013.01.078. Epub 2013 Feb 4.
3
Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.通过腙和芳炔的反应合成邻-(二甲氨基)芳基酮、吖啶酮、吖啶鎓盐和 1H-吲唑。
J Org Chem. 2012 Dec 21;77(24):11232-56. doi: 10.1021/jo302378w. Epub 2012 Dec 3.
4
Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.通过 1,1-二烷基腙和芳炔的反应合成邻-（二甲氨基）芳基酮和吖啶酮。
Org Lett. 2011 Aug 5;13(15):4136-9. doi: 10.1021/ol2016803. Epub 2011 Jul 11.
5
DDQ-catalyzed oxidative C--O coupling of sp³ C--H bonds with carboxylic acids.DDQ催化的sp³ C-H键与羧酸的氧化C-O偶联反应。
ChemSusChem. 2012 Nov;5(11):2143-6. doi: 10.1002/cssc.201200458. Epub 2012 Nov 5.
6
An efficient conversion of carboxylic acids to one-carbon degraded aldehydes via 2-hydroperoxy acids.通过2-氢过氧酸将羧酸高效转化为一碳降解醛。
Biosci Biotechnol Biochem. 2007 May;71(5):1370-1. doi: 10.1271/bbb.70105. Epub 2007 May 7.
7
Cross-coupling of alkenyl/aryl carboxylates with Grignard reagent via Fe-catalyzed C-O bond activation.通过铁催化的 C-O 键活化实现烯基/芳基羧酸酯与格氏试剂的交叉偶联。
J Am Chem Soc. 2009 Oct 21;131(41):14656-7. doi: 10.1021/ja907281f.
8
Group Exchange between Ketones and Carboxylic Acids through Directing Group Assisted Rh-Catalyzed Reorganization of Carbon Skeletons.通过导向基团辅助的 Rh 催化重排碳骨架实现酮和羧酸之间的基团交换。
J Am Chem Soc. 2015 Apr 22;137(15):5012-20. doi: 10.1021/ja512003d. Epub 2015 Apr 14.
9
Mechanism-Driven Development of Group 10 Metal-Catalyzed Decarbonylative Coupling Reactions.基于机理的 Group 10 金属催化脱羰偶联反应的发展。
Acc Chem Res. 2022 Dec 6;55(23):3430-3444. doi: 10.1021/acs.accounts.2c00496. Epub 2022 Nov 16.
10
Convenient synthesis of ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates and 4-aryl-6-(trifluoromethyl)-2H-pyran-2-ones: novel highly reactive CF3-containing building blocks.4-芳基-6-(三氟甲基)-2-氧代-2H-吡喃-3-羧酸乙酯和4-芳基-6-(三氟甲基)-2H-吡喃-2-酮的简便合成：新型高反应性含CF3的构建单元
Org Lett. 2008 Jul 3;10(13):2857-9. doi: 10.1021/ol800992z. Epub 2008 Jun 7.
引用本文的文献
1
Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity.氟化2-芳基苯并二氢吡喃-4-酮及其衍生物：合成、结构与抗病毒活性
Mol Divers. 2024 Dec;28(6):3635-3660. doi: 10.1007/s11030-023-10769-6. Epub 2023 Dec 28.
2
Polyphosphoric acid-promoted one-pot synthesis and neuroprotective effects of flavanones against NMDA-induced injury in PC12 cells.多聚磷酸促进的黄烷酮类化合物的一锅法合成及其对PC12细胞中NMDA诱导损伤的神经保护作用。
RSC Adv. 2022 Oct 3;12(43):28098-28103. doi: 10.1039/d2ra03562f. eCollection 2022 Sep 28.
3
Nitrogen-Rich Porous Organic Polymers with Supported Ag Nanoparticles for Efficient CO Conversion.负载银纳米颗粒的富氮多孔有机聚合物用于高效CO转化
Nanomaterials (Basel). 2022 Sep 6;12(18):3088. doi: 10.3390/nano12183088.
4
Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A.作为核心策略，苯并环的组装用于合成异吲哚啉酮天然产物异海灵菌素、埃里纳塞林 A 和甾烯灵 A。
Org Lett. 2021 Oct 1;23(19):7550-7554. doi: 10.1021/acs.orglett.1c02752. Epub 2021 Sep 20.
5
Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones.甲氧基取代的γ-氧代-ε-内酰胺的合成及其抗菌活性。
Molecules. 2019 Nov 16;24(22):4151. doi: 10.3390/molecules24224151.
6
Intermolecular C-O Addition of Carboxylic Acids to Arynes: Synthesis of -Hydroxyaryl Ketones, Xanthones, 4-Chromanones, and Flavones.羧酸与芳炔的分子间碳-氧加成反应：α-羟基芳基酮、呫吨酮、4-色满酮和黄酮的合成
Tetrahedron. 2013 Apr 1;69(13):2789-2798. doi: 10.1016/j.tet.2013.01.078. Epub 2013 Feb 4.
7
Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones.对2,3-吡啶炔的亲核加成反应及苯并萘啶酮的合成。
Tetrahedron. 2012 Apr 1;68(13):2819-2826. doi: 10.1016/j.tet.2012.02.002. Epub 2012 Feb 9.
8
Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.通过腙和芳炔的反应合成邻-(二甲氨基)芳基酮、吖啶酮、吖啶鎓盐和 1H-吲唑。
J Org Chem. 2012 Dec 21;77(24):11232-56. doi: 10.1021/jo302378w. Epub 2012 Dec 3.
9
Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.钯催化芳炔与邻卤代苯甲酰胺的环化反应：菲啶酮的合成。
J Org Chem. 2012 Oct 5;77(19):8648-56. doi: 10.1021/jo3016192. Epub 2012 Sep 26.
10
Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.芳炔与β-内酰胺和二氢喹啉酮反应中通过乙烯挤出形成吖啶酮。
J Org Chem. 2012 Jul 20;77(14):6262-70. doi: 10.1021/jo3011073. Epub 2012 Jul 10.
本文引用的文献
1
Synthesis of benzisoxazoles by the [3 + 2] cycloaddition of in situ generated nitrile oxides and arynes.通过原位生成的腈氧化物和芳炔的[3 + 2]环加成反应合成苯并异恶唑。
Org Lett. 2010 Mar 19;12(6):1180-3. doi: 10.1021/ol902921s.
2
Synthesis of N-arylated 1,2-dihydroheteroaromatics through the three-component reaction of arynes with N-heteroaromatics and terminal alkynes or ketones.通过芳炔与 N-杂芳环和末端炔烃或酮的三组分反应合成 N-芳基 1,2-二氢杂芳烃。
Chem Asian J. 2010 Jan 4;5(1):153-9. doi: 10.1002/asia.200900324.
3
Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides.将苯环插入酰胺键中：一步法从芳基酰胺合成吖啶和吖啶酮。
Org Lett. 2010 Jan 1;12(1):168-71. doi: 10.1021/ol902568x.
4
Naturally occurring xanthones; latest investigations: isolation, structure elucidation and chemosystematic significance.天然黄烷酮；最新研究进展：分离、结构鉴定及化学系统学意义。
Curr Med Chem. 2009;16(20):2581-626. doi: 10.2174/092986709788682056.
5
Recent cancer drug development with xanthone structures.近期含氧杂蒽酮结构的抗癌药物研发
J Pharm Pharmacol. 2009 Jun;61(6):707-12. doi: 10.1211/jpp/61.06.0002.
6
Reaction of benzyne with salicylaldehydes: general synthesis of xanthenes, xanthones, and xanthols.苯炔与水杨醛的反应：呫吨、呫吨酮和呫吨醇的通用合成方法
Org Lett. 2009 Jan 1;11(1):169-71. doi: 10.1021/ol802597x.
7
Insertion of arynes into carbon-halogen sigma-bonds: regioselective acylation of aromatic rings.芳炔插入碳-卤西格玛键：芳环的区域选择性酰化反应
Chem Commun (Camb). 2007 Jun 21(23):2405-7. doi: 10.1039/b701581j.
8
Intermolecular C-N addition of amides and S-N addition of sulfinamides to arynes.酰胺的分子间C-N加成以及亚磺酰胺与芳炔的S-N加成。
J Am Chem Soc. 2005 Sep 28;127(38):13112-3. doi: 10.1021/ja054079p.
9
The direct acyl-alkylation of arynes.芳炔的直接酰基烷基化反应。
J Am Chem Soc. 2005 Apr 20;127(15):5340-1. doi: 10.1021/ja050859m.
10
Anti-inflammatory plant flavonoids and cellular action mechanisms.抗炎植物黄酮类化合物及其细胞作用机制。
J Pharmacol Sci. 2004 Nov;96(3):229-45. doi: 10.1254/jphs.crj04003x. Epub 2004 Nov 12.
Zotero 插件