| 水相中5-（嘌呤-6-巯基）邻苯二酚衍生物的电化学合成 |
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| 引用本文： | 刘福建a,b,曾程初a,平大为a,蔡远利b,钟儒刚a.水相中5-（嘌呤-6-巯基）邻苯二酚衍生物的电化学合成[J].中国化学,2008,26(9):1651-1655. |
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| 作者姓名： | 刘福建a b 曾程初a 平大为a 蔡远利b 钟儒刚a |
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| 作者单位： | a北京工业大学生命科学与生物工程学院，北京100124 ;b湘潭大学化学学院,湖南湘潭411105 ; |
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| 摘 要： | 本文报道了6-巯基嘌呤存在时在水相中通过阳极氧化邻苯二酚来电化学合成5-(嘌呤-6-巯基)邻苯二酚衍生物。循环伏安法和控制电位电解的结果表明该类化合物的形成为EC过程，即邻苯二酚衍生物原料先是被电化学氧化成对应的邻苯醌衍生物，该醌非常活泼，进一步与6-巯基嘌呤发生迈克尔加成反应，原位转化生成化合物3a-3d。该工作进一步证明了水相中邻苯醌衍生物的电化学合成与原位转化是合成邻苯二酚衍生物的重要方法。
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| 关 键 词： | 电化学合成 6-巯基嘌呤 邻苯二酚 |
| 收稿时间： | 2008-2-20 |
| 修稿时间： | 2008-4-10 |
Electrochemical Synthesis of 5‐Purin‐6'‐ylthiocatechols in Aqueous Medium |
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| Fu‐Jian LIU,Cheng‐Chu ZENG,Da‐Wei PING,Yuan‐Li CAI,Ru‐Gang ZHONG.Electrochemical Synthesis of 5‐Purin‐6'‐ylthiocatechols in Aqueous Medium[J].Chinese Journal of Chemistry,2008,26(9):1651-1655. |
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| Authors: | Fu‐Jian LIU Cheng‐Chu ZENG Da‐Wei PING Yuan‐Li CAI Ru‐Gang ZHONG |
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| Institution: | 1. College of Life Science & Bioengineering, Beijing University of Technology, Beijing 100124, China;2. College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, China;3. Tel.: 0086‐010‐67396211;4. Fax: 0086‐010‐67392001 |
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| Abstract: | The electrochemical synthesis of 5‐purin‐6′‐ylthiocatechols was carried out by anodic oxidation of catechol derivatives 1a – 1d in the presence of 6‐mercaptopurine ( 2 ) in aqueous solution. Results of cyclic voltammetry and controlled‐potential electrolysis indicated that the starting catechols were first oxidized to the corresponding o‐benzoquinone, which underwent further Michael addition with 6‐mercaptopurine to produce titled products 3a – 3d following an EC (E=electrochemical and C=chemical step) mechanism. Such work further demonstrates the versatility of the anodic oxidation of catechols and their in‐situ transformation for the synthesis of derivatized catechols. |
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| Keywords: | electrochemical synthesis 6‐mercaptopurine catechols |
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