Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers

Krishna T. P. Adarsh; Pandaram Sakthivel; Chinnasamy Suresh; Ilangovan Andivelu

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Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers

机译：使用铬酸的胆管醌和硫醇的氧化自由基偶联：单罐合成喹啉烷基/芳基硫醚

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An efficient, simple and practical protocol for one-pot sequential oxidative radical C-H/S-H cross-coupling of thiols with hydroquinones (HQs) and oxidation leading to the formation of quinonyl alkyl/aryl thioethers using H2CrO4 was developed. This cross-coupling of thiyl and aryl radicals offers mono thioethers in good to moderate yield and works well with a wide variety of thiols. Similarly, this method works well for coupling of 2-amino thiophenol and HQs to form phenothiazine-3-ones 5a-c. C-S bond formation via thioether synthesis was observed using a chromium reagent for the first time. Theoretical studies on the pharmacokinetic properties of compounds 5a-c revealed that due to drug-like properties, compound 5b strongly binds with Alzheimer's disease (AD) associated AChE target sites.

机译：开发了一种高效，简单，实用的硫醇与氢醌（HQS）的硫醇序列氧化基团C-H / S-H交叉偶联，氧化导致使用H2Cro 4形成醌基烷基/芳基硫醚的氧化剂。这种硫基和芳基的交叉偶联是单硫醚，良好的产量很好，并与各种硫醇均匀。类似地，该方法适用于2-氨基噻吩酚和HQs形成吩噻嗪-3-℃的偶联。首次使用铬试剂观察通过硫醚合成的C-S键形成。关于化合物5A-C的药代动力学性质的理论研究表明，由于药物样性能，化合物5B与阿尔茨海默病（AD）相关的ACHE靶位点强烈结合。

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《RSC Advances》 |2020年第33期|共9页
作者
Krishna T. P. Adarsh; Pandaram Sakthivel; Chinnasamy Suresh; Ilangovan Andivelu;
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Bharathidasan Univ Sch Chem Tiruchirappalli 620024 Tamil Nadu India;

Bharathidasan Univ Sch Chem Tiruchirappalli 620024 Tamil Nadu India;

Bharathidasan Univ Sch Chem Tiruchirappalli 620024 Tamil Nadu India;

Bharathidasan Univ Sch Chem Tiruchirappalli 620024 Tamil Nadu India;

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正文语种 eng
中图分类化学;
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1. Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers [J] . Krishna T. P. Adarsh, Pandaram Sakthivel, Chinnasamy Suresh, RSC Advances . 2020,第33期

机译：使用铬酸的胆管醌和硫醇的氧化自由基偶联：单罐合成喹啉烷基/芳基硫醚
2. One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium- Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate [J] . Manuel A. Fernndez-Rodrguez, John F. Hartwig Chemistry: A European journal . 2010,第8期

机译：钯催化偶联的两个芳基溴化物和硫醇替代物一锅法合成不对称二芳基硫醚
3. One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium-Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate [J] . Manuel A. Fernaacute, ndez-Rodriacute, guez Dr., Chemistry - A European Journal . 2010,第8期

机译：钯催化偶联的两个芳基溴化物和硫醇替代物一锅法合成不对称二芳基硫醚
4. Micro-reactor synthesis: synthesis of cyanobiphenyls using a modified suzuki coupling of an aryl halide and aryl boronic acid. [C] . Victoria Skelton, Gillian M.Greenway, Stephen J.Haswell, International conference on microreaction technology . 2000

机译：微反应器合成：使用芳基卤化物和芳族硼酸的改性铃木偶联来合成氰基苯基。
5. THE PREPARATION OF SOME 1-ALKYL-1,2,3,4-TETRAZOLE-5-THIOL AND 1-ARYL-1,2,3,4-TETRAZOLE-5-THIOL AND 3-ALKYLTETRAHYDRO-QUINAZOLINE-2-THIOL AND 3-ARYLTETRAHYDRO-QUINAZOLINE-2-THIOL COMPOUNDS AND THEIR INTERMEDIATES. [D] . ORTH, RONALD EMERSON. 1960

机译：制备一些1-烷基-1,2,3,4-四唑-5-硫醇和1-ARY-1,2,3,4-四唑-5-硫醇和3-烷基-喹啉-2-噻吩及3-芳基-喹啉-2-硫醇化合物及其中间体。
6. One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium-Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate [O] . Dr. Manuel A. Fernández-Rodríguez, Prof. Dr. John F. Hartwig -1

机译：用钯催化两种芳溴化物和硫醇替代物的钯催化偶联的单壶合成非对称二芳基醚
7. Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers [O] . T. P. Adarsh Krishna, Sakthivel Pandaram, Suresh Chinnasamy, 2020

机译：使用铬酸的胆管醌和硫醇的氧化自由基偶联：单罐合成喹啉烷基/芳基硫醚

Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers

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