通过芳炔与取代苯甲酸酯的偶联反应合成呫吨酮、噻吨酮和吖啶酮。
Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.
作者信息
Zhao Jian, Larock Richard C
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
J Org Chem. 2007 Jan 19;72(2):583-8. doi: 10.1021/jo0620718.
Abstract
The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.
摘要
甲硅烷基芳基三氟甲磺酸酯、氟化铯与邻位杂原子取代的苯甲酸酯的反应为制备具有生物学意义的呫吨酮、硫代呫吨酮和吖啶酮提供了一种通用且高效的方法。该化学过程可能是通过苯甲酸酯与芳炔的串联分子间亲核偶联以及随后的分子内亲电环化来进行的。
相似文献
1
Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.通过芳炔与取代苯甲酸酯的偶联反应合成呫吨酮、噻吨酮和吖啶酮。
J Org Chem. 2007 Jan 19;72(2):583-8. doi: 10.1021/jo0620718.
2
One-pot synthesis of xanthones and thioxanthones by the tandem coupling-cyclization of arynes and salicylates.通过芳炔和水杨酸酯的串联偶联-环化一锅法合成呫吨酮和噻吨酮。
Org Lett. 2005 Sep 15;7(19):4273-5. doi: 10.1021/ol0517731.
3
Synthesis of fluorinated benzophenones, xanthones, acridones, and thioxanthones by iterative nucleophilic aromatic substitution.通过迭代亲核芳香取代合成氟化二苯甲酮、黄酮、吖啶酮和噻吨酮。
J Org Chem. 2012 Jan 6;77(1):473-81. doi: 10.1021/jo202062f. Epub 2011 Nov 23.
4
Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.通过使用可见光和分子氧的无金属光催化氧化合成呫吨酮、噻吨酮和吖啶酮。
Molecules. 2021 Feb 12;26(4):974. doi: 10.3390/molecules26040974.
5
Synthesis of 9-Substituted Xanthenes by the Condensation of Arynes with ortho-Hydroxychalcones.通过芳烃与邻羟基查耳酮的缩合反应合成9-取代氧杂蒽
Tetrahedron Lett. 2012 Apr 25;53(17):2202-2205. doi: 10.1016/j.tetlet.2012.02.072. Epub 2012 Feb 25.
6
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.
7
Synthesis of acridines by the [4 + 2] annulation of arynes and 2-aminoaryl ketones.通过芳炔与 2-氨基芳基酮的[4 + 2]环加成反应合成吖啶。
J Org Chem. 2010 Apr 2;75(7):2289-95. doi: 10.1021/jo1000687.
8
Oxiranylmethyloxy or thiiranylmethyloxy-azaxanthones and -acridone analogues as potential topoisomerase I inhibitors.氧杂环丁烷甲基氧基或硫杂环丁烷甲基氧基-氮杂蒽酮和吖啶酮类似物作为潜在的拓扑异构酶 I 抑制剂。
Bioorg Med Chem Lett. 2009 Dec 1;19(23):6766-9. doi: 10.1016/j.bmcl.2009.09.091. Epub 2009 Sep 27.
9
Cascade nucleophilic addition-cyclic Michael addition of arynes and phenols/anilines bearing ortho alpha,beta-unsaturated groups: facile synthesis of 9-functionalized xanthenes/acridines.芳炔和邻位α,β-不饱和基团取代的酚/苯胺的级联亲核加成-环迈克尔加成：9-官能化呫吨/吖啶的简便合成。
J Org Chem. 2010 Jan 15;75(2):506-9. doi: 10.1021/jo902311a.
10
Unprecedented ipso aromatic nucleophilic substitution upon oxidative decarboxylation of tris(p-carboxyltetrathiaaryl)methyl (TAM) radicals: a new access to diversely substituted TAM radicals.未曾预料的三（对羧基四硫杂苯甲叉基）甲基（TAM）自由基氧化脱羧时的同芳香亲核取代反应：一种获得各种取代 TAM 自由基的新途径。
Chem Commun (Camb). 2011 Apr 28;47(16):4805-7. doi: 10.1039/c1cc10426h. Epub 2011 Mar 16.
引用本文的文献
1
Intramolecular Friedel-Crafts Reaction with Trifluoroacetic Acid: Synthesizing Some New Functionalized 9-Aryl/Alkyl Thioxanthenes.与三氟乙酸的分子内傅克反应：合成一些新型官能化9-芳基/烷基噻吨
ACS Omega. 2024 Mar 8;9(11):12596-12601. doi: 10.1021/acsomega.3c07150. eCollection 2024 Mar 19.
2
Transition-metal-free intramolecular Friedel-Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives.通过烯烃活化实现的无过渡金属分子内傅克反应：一种合成某些新型呫吨衍生物的方法。
Beilstein J Org Chem. 2021 Aug 30;17:2203-2208. doi: 10.3762/bjoc.17.142. eCollection 2021.
3
Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.通过使用可见光和分子氧的无金属光催化氧化合成呫吨酮、噻吨酮和吖啶酮。
Molecules. 2021 Feb 12;26(4):974. doi: 10.3390/molecules26040974.
4
Sustainable Access to Acridin-9-(10)ones with an Embedded -Terphenyl Moiety Based on a Three-Component Reaction.基于三组分反应的含嵌入 -三联苯部分的吖啶-9-(10)-酮的可持续获取。
Molecules. 2020 Nov 27;25(23):5565. doi: 10.3390/molecules25235565.
5
-Quinone Methide Driven Synthesis of New ,- or ,-Heterocycles.- 醌甲基化物驱动的新型α-或β-杂环的合成。
ChemistryOpen. 2019 Jul 16;8(7):961-971. doi: 10.1002/open.201900150. eCollection 2019 Jul.
6
Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.芳炔的三组分偶联反应在苯并呋喃和香豆素合成中的应用。
Molecules. 2014 Jan 13;19(1):863-80. doi: 10.3390/molecules19010863.
7
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.
8
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.
9
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.
10
Copper-catalyzed ortho-acylation of phenols with aryl aldehydes and its application in one-step preparation of xanthones.铜催化酚与芳醛的邻位酰化及其在一步法制备黄酮中的应用。
Chem Commun (Camb). 2012 Nov 25;48(91):11256-8. doi: 10.1039/c2cc36176k. Epub 2012 Oct 15.
本文引用的文献
1
Synthesis of acridone derivatives using polymer-supported palladium and scandium catalysts.使用聚合物负载钯和钪催化剂合成吖啶酮衍生物。
J Comb Chem. 2006 Jul-Aug;8(4):459-61. doi: 10.1021/cc060011+.
2
Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity.具有拓扑异构酶活性的吖啶和吖啶酮类抗疱疹药物的合成与评价
Bioorg Med Chem. 2006 Aug 15;14(16):5467-80. doi: 10.1016/j.bmc.2006.04.044. Epub 2006 May 19.
3
Synthesis and anti-BVDV activity of acridones as new potential antiviral agents.作为新型潜在抗病毒药物的吖啶酮类化合物的合成及其抗牛病毒性腹泻病毒活性
J Med Chem. 2006 Apr 20;49(8):2621-7. doi: 10.1021/jm051250z.
4
Anionic N-fries rearrangement of N-carbamoyl diarylamines to anthranilamides. Methodology and application to acridone and pyranoacridone alkaloids.N-氨基甲酰基二芳基胺向邻氨基苯甲酰胺的阴离子N-弗里斯重排。方法及其在吖啶酮和吡喃吖啶酮生物碱中的应用。
Org Lett. 2006 Mar 16;8(6):1133-6. doi: 10.1021/ol053162e.
5
Xanthone derivatives from Cratoxylum cochinchinense roots.来自越南黄牛木根的呫吨酮衍生物。
Phytochemistry. 2006 Mar;67(5):470-4. doi: 10.1016/j.phytochem.2005.10.008. Epub 2005 Nov 28.
6
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.
7
One-pot synthesis of xanthones and thioxanthones by the tandem coupling-cyclization of arynes and salicylates.通过芳炔和水杨酸酯的串联偶联-环化一锅法合成呫吨酮和噻吨酮。
Org Lett. 2005 Sep 15;7(19):4273-5. doi: 10.1021/ol0517731.
8
Regioselective ortho lithiation of 3-aryl and 3-styryl furans.3-芳基和3-苯乙烯基呋喃的区域选择性邻位锂化反应。
Org Lett. 2005 Jul 21;7(15):3347-50. doi: 10.1021/ol051205l.
9
Palladium-catalyzed cross-coupling reactions in total synthesis.钯催化交叉偶联反应在全合成中的应用
Angew Chem Int Ed Engl. 2005 Jul 18;44(29):4442-89. doi: 10.1002/anie.200500368.
10
A convenient route to diverse heterocycles through an addition of beta-amino carbonyl compounds to 3-halogeno-4-methoxybenzynes.通过将β-氨基羰基化合物加成到3-卤代-4-甲氧基苯炔上制备多种杂环化合物的便捷方法。
J Org Chem. 2005 Jul 8;70(14):5741-4. doi: 10.1021/jo050420c.
Zotero 插件