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化学产生邻醌单亚胺,快速构建 1,4-苯并恶嗪衍生物。

Chemical generation of o-quinone monoimines for the rapid construction of 1,4-benzoxazine derivatives.

机构信息

Department of Chemistry, Indian Institute of Technology, Roorkee-247 667, Uttarakhand, India.

出版信息

Org Biomol Chem. 2012 Mar 14;10(10):1958-61. doi: 10.1039/c2ob06681e. Epub 2012 Jan 27.

DOI:10.1039/c2ob06681e
PMID:22286300
Abstract

Highly reactive o-benzoquinone monoimines were chemically generated and successfully trapped with electron-rich olefins that led to the synthesis of hitherto unknown 1,4-benzoxazine derivatives. This unprecedented transformation was achieved by the oxidation of o-aminophenols bearing appropriate functionality on the arene residue with less expensive hypervalent iodine reagent in the presence of vinylic ethers or thioethers.

摘要

高反应性邻苯醌单亚胺通过化学方法生成,并成功地与富电子烯烃捕获,导致了前所未知的 1,4-苯并恶嗪衍生物的合成。这种前所未有的转化是通过在烯丙基醚或硫醚存在下,用较便宜的高价碘试剂氧化芳基残留物上带有适当官能团的邻氨基酚来实现的。

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1
Chemical generation of o-quinone monoimines for the rapid construction of 1,4-benzoxazine derivatives.化学产生邻醌单亚胺,快速构建 1,4-苯并恶嗪衍生物。
Org Biomol Chem. 2012 Mar 14;10(10):1958-61. doi: 10.1039/c2ob06681e. Epub 2012 Jan 27.
2
Hypervalent iodine mediated synthesis of carbamate protected p-quinone monoimine ketals and p-benzoquinone monoketals.高价碘介导的氨基甲酸酯保护的对苯醌单亚胺缩酮和对苯醌单酮的合成。
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Catalytic hypervalent iodine oxidation using 4-iodophenoxyacetic acid and oxone: oxidation of p-alkoxyphenols to p-benzoquinones.使用4-碘苯氧基乙酸和过氧单硫酸钾的催化高价碘氧化反应:对烷氧基苯酚氧化为对苯醌。
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Activation and detoxication of aminophenols. III. Synthesis and structural elucidation of various glutathione addition products to 1,4-benzoquinone.
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Reduction and glutathione conjugation reactions of N-acetyl-p-benzoquinone imine and two dimethylated analogues.N-乙酰对苯醌亚胺及其两种二甲基化类似物的还原反应和谷胱甘肽共轭反应。
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Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based alpha,alpha-amino esters.通过醌基 α,α-氨基酸酯的氧化脱羧反应,前所未有地合成了一种新型的氨基醌环系统。
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Microwave-mediated Claisen rearrangement followed by phenol oxidation: a simple route to naturally occurring 1,4-benzoquinones. The first syntheses of verapliquinones A and B and panicein A.微波介导的克莱森重排反应随后进行苯酚氧化:一条合成天然存在的1,4-苯醌的简便途径。维拉醌A和B以及panicin A的首次合成。
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Density functional theory study on the formation of reactive benzoquinone imines by hydrogen abstraction.密度泛函理论研究氢提取反应性苯醌亚胺的形成。
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Comparative cytotoxic effects of N-acetyl-p-benzoquinone imine and two dimethylated analogues.N-乙酰对苯醌亚胺及其两种二甲基化类似物的细胞毒性比较
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