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CDC 反应及后续环化合成 2-羟基-3-烷基-1,4-萘醌和吡喃萘醌。

CDC Reaction and Subsequent Cyclization for the Synthesis of 2-Hydroxy-3-alkyl-1,4-naphthoquinones and Pyranonaphthoquinones.

机构信息

College of Pharmaceutical Science, Zhejiang University of Technology , Hangzhou 310014, P. R. China.

College of Chemical Engineering, Zhejiang University of Technology , Hangzhou 310014, P. R. China.

出版信息

J Org Chem. 2017 Feb 3;82(3):1610-1617. doi: 10.1021/acs.joc.6b02787. Epub 2017 Jan 17.

DOI:10.1021/acs.joc.6b02787
PMID:28034312
Abstract

The metal-free cross-dehydrogenative coupling (CDC) reaction and subsequent cyclization of 2-hydroxy-1,4-naphthoquinone (lawsone) and 1,3-diarylpropene promoted by DDQ has been developed. 2-Hydroxy-3-alkyl-1,4-naphthoquinones and pyranonaphthoquinones with potential pharmaceutical applications are obtained in moderate to good yields. The reaction is also compatible for 4-hydroxycoumarins.

摘要

无金属的交叉脱氢偶联(CDC)反应和随后的 2-羟基-1,4-萘醌(lawsone)和 1,3-二芳基丙烯在 DDQ 促进下的环化反应已经被开发出来。得到了具有潜在药物应用的 2-羟基-3-烷基-1,4-萘醌和吡喃并萘醌,产率中等至良好。该反应也适用于 4-羟基香豆素。

相似文献

1
CDC Reaction and Subsequent Cyclization for the Synthesis of 2-Hydroxy-3-alkyl-1,4-naphthoquinones and Pyranonaphthoquinones.CDC 反应及后续环化合成 2-羟基-3-烷基-1,4-萘醌和吡喃萘醌。
J Org Chem. 2017 Feb 3;82(3):1610-1617. doi: 10.1021/acs.joc.6b02787. Epub 2017 Jan 17.
2
-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions.-无金属条件下丁基过氧化氢(TBHP)介导的喹喔啉-2(1H)-酮与 4-羟基香豆素、4-羟基-6-甲基-2-吡喃酮和 2-羟基-1,4-萘醌的氧化交叉脱氢偶联。
Org Biomol Chem. 2020 Aug 26;18(33):6537-6548. doi: 10.1039/d0ob01304h.
3
5-Hydroxy-1,4-naphthoquinone (juglone) and 2-hydroxy-1,4-naphthoquinone (lawsone) influence on jack bean urease activity: Elucidation of the difference in inhibition activity.5-羟基-1,4-萘醌(胡桃醌)和 2-羟基-1,4-萘醌(洛索洛芬)对豇豆脲酶活性的影响:抑制活性差异的阐明。
Bioorg Chem. 2010 Jun;38(3):132-7. doi: 10.1016/j.bioorg.2010.02.002. Epub 2010 Feb 13.
4
Diastereoselective Construction of -2-Alkyl-6-aryl-3,6-dihydro-2-pyrans via Dehydrogenative Cycloetherification Promoted by DDQ.手性 2-烷基-6-芳基-3,6-二氢-2-吡喃的通过 DDQ 促进的脱氢环醚化反应构建
Org Lett. 2021 Feb 5;23(3):1135-1140. doi: 10.1021/acs.orglett.1c00154. Epub 2021 Jan 25.
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Synthesis and biological evaluation of novel ferrocene-naphthoquinones as antiplasmodial agents.新型二茂铁萘醌类化合物的合成及抗疟活性评价。
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6
HFIP Promoted C3 Alkylation of Lawsone and 4-Hydroxycoumarin with Alcohols by Dehydrative Cross-Coupling.HFIP 促进大黄素和 4-羟基香豆素与醇的脱水交叉偶联的 C3 烷基化反应。
J Org Chem. 2020 Aug 21;85(16):10638-10647. doi: 10.1021/acs.joc.0c01207. Epub 2020 Aug 6.
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Highly enantioselective synthesis of naphthoquinones and pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides.双功能手性双方酰胺催化萘醌和吡喃萘醌的高度对映选择性合成。
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Correction: tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions.更正:叔丁基过氧化氢(TBHP)介导喹喔啉-2(1H)-酮与4-羟基香豆素、4-羟基-6-甲基-2-吡喃酮和2-羟基-1,4-萘醌在无金属条件下的氧化交叉脱氢偶联反应。
Org Biomol Chem. 2020 Sep 21;18(35):6965-6966. doi: 10.1039/d0ob90117b. Epub 2020 Sep 3.
9
Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis.通过顺序使用方酰胺和银催化对4H-吡喃萘醌进行对映选择性合成。
Chem Commun (Camb). 2016 Jan 28;52(8):1669-72. doi: 10.1039/c5cc09592a. Epub 2015 Dec 14.
10
Palladium(II)-Catalyzed C-H Bond Activation/C-C Coupling/Intramolecular Tsuji-Trost Reaction Cascade: Facile Access to 2H-Pyranonaphthoquinones.钯(II)催化的 C-H 键活化/C-C 偶联/分子内 Tsuji-Trost 反应级联反应:易于获得 2H-吡喃并萘醌。
Org Lett. 2015 Jul 17;17(14):3410-3. doi: 10.1021/acs.orglett.5b01304. Epub 2015 Jul 7.

引用本文的文献

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Metal-Free Direct C-H Functionalization of Quinoxalin-2(1)-Ones to Produce 3-Vinylated Quinoxalin-2(1)-Ones in the Presence of Alkenes.在烯烃存在下,喹喔啉-2(1)-酮的无金属直接C-H官能化反应制备3-乙烯基喹喔啉-2(1)-酮
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