Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives

Song Chunlan; Liu Kun; Jiang Xu; Dong Xin; Weng Yue; Chiang Chien‐Wei; Lei Aiwen

摘要

Abstract > Dearomative annulation of indoles has emerged as a powerful tool for the preparation of polycyclic indoline‐based alkaloids. Compared with well‐established methods towards five‐membered‐ring‐fused indolines, the six‐membered‐ring‐fused indolines are rarely accessed under thermal conditions. Herein, a dearomative [4+2] annulation between different indoles is developed through an electrochemical pathway. This transformation offers a remarkably regio‐ and stereoselective route to highly functionalized pyrimido[5,4‐ b ]indoles under oxidant‐ and metal‐free conditions. Notably, this electrochemical approach maintains excellent functional‐group tolerance and can be extended as a modification tactic for pharmaceutical research. Preliminary mechanism studies indicate that the electrooxidation annulation proceeds through radical–radical cross‐coupling between an indole radical cation and an N‐centered radical generated in?situ. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 吲哚的亲爱的装载是制备多环吲哚氨基生物碱的强大工具。与朝向五元环熔融吲哚吲哚的良好方法相比，在热条件下很少进入六元环熔吲哚吲哚。这里，通过电化学途径开发不同吲哚之间的亲爱的[4 + 2]环节。该转变提供了一个显着的重生和立体选择性的途径，以高度官能化嘧啶[5,4- b </ i> ]氧化剂和无金属条件下的吲哚。值得注意的是，这种电化学方法保持了优异的功能基团公差，并且可以作为药物研究的修改策略延伸。初步机制研究表明，电氧化环测量通过吲哚自由基阳离子和产生的N中心基团之间的自由基 - 自由基交叉耦合进行。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第18期</span><b style="margin: 0 2px;">|</b><span>共5页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Song Chunlan&option=202" target="_blank" rel="nofollow">Song Chunlan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Kun&option=202" target="_blank" rel="nofollow">Liu Kun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jiang Xu&option=202" target="_blank" rel="nofollow">Jiang Xu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Dong Xin&option=202" target="_blank" rel="nofollow">Dong Xin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Weng Yue&option=202" target="_blank" rel="nofollow">Weng Yue;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chiang Chien‐Wei&option=202" target="_blank" rel="nofollow">Chiang Chien‐Wei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lei Aiwen&option=202" target="_blank" rel="nofollow">Lei Aiwen;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> <p>College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS)Wuhan UniversityWuhan 430072 Hubei P. R. China;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=4+2 annulation&option=203" rel="nofollow">4+2 annulation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=dearomative annulation&option=203" rel="nofollow">dearomative annulation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=electrosynthesis&option=203" rel="nofollow">electrosynthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=indole&option=203" rel="nofollow">indole;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=pyrimido5&option=203" rel="nofollow">pyrimido5;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=4-bindoles&option=203" rel="nofollow">4-bindoles;</a> </p> <div class="translation"> 机译：[4 + 2]例子;脱胶;电池;吲哚;嘧啶[5;4-B]吲哚; 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href="/journal-cn-3868/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 平原大学学报 </a> </span> <span> . 2001</span><span>,第002期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-14096_thesis/020221062620.html">德兴铜矿辉钼矿精矿的选择性电氧化浸出与分离过程研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=钟宏&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 钟宏</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=曹占芳&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,曹占芳</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=邱朝辉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,邱朝辉</a> <span> <a href="/conference-cn-14096/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第六届全国化学工程与生物化工年会 </a> <span> <span> . 2010</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314940916.html">机械力促进的交叉脱氢偶联反应用于制备吲哚衍生物</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张扬&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张扬</a> <span> . 2017</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061201283469.html">作为选择性11-β-羟基类固醇脱氢酶1型抑制剂的7-氮杂吲哚衍生物</a> <b>[P]</b> . <span> 中国专利： CN101848910B </span> <span> . 2013.12.04</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120106042958.html">作为选择性11-β-羟基类固醇脱氢酶1型抑制剂的7-氮杂吲哚衍生物</a> <b>[P]</b> . <span> 中国专利： CN101848910A </span> <span> . 2010-09-29</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130446504988.html">Novel prodrugs von 6-hydroxy-2,3-dihydro-1h-indoles, 5-hydroxy-1,2-dihydro-3h-pyrrolo(3,2-e)indoles and 5-hydroxy-1,2-dihydro-3h-benzo(e)indoles as well as of 6-hydroxy-1,2,3,4-tetrahydro-benzo(f)quinoline derivatives for use in selective cancer therapy</a> <b>[P]</b> . <span> 外国专利：  AU7398301A </span> <span> . 2001-11-12</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：新型前药von 6-hydroxy-2,3-dihydro-1h-indoles，5-hydroxy-1,2-dihydro-3h-pyrrolo（3,2-e）indoles and 5-hydroxy-1,2-dihydro-3h -苯并（e）吲哚以及6-羟基-1,2,3,4-四氢-苯并（f）喹啉衍生物，用于选择性癌症治疗 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130441865339.html">NOVEL PRODRUGS VON 6-HYDROXY-2,3-DIHYDRO-1H-INDOLES, 5-HYDROXY-1,2-DIHYDRO-3H-PYRROLO 3,2-EINDOLES AND 5-HYDROXY-1,2-DIHYDRO-3H-BENZO(E)INDOLES AS WELL AS OF 6-HYDROXY-1,2,3,4-TETRAHYDRO-BENZO FQUINOLINE DERIVATIVES FOR USE IN SELECTIVE CANCER THERAPY</a> <b>[P]</b> . <span> 外国专利：  EP1280771B1 </span> <span> . 2004-10-13</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：新产品VON 6-HYDROXY-2,3-DIHYDRO-1H-吲哚，5-HYDROXY-1,2-DIHYDRO-3H-PYRROLO 3,2-E]吲哚和5-HYDROXY-1,2-DIHYDRO-3H-苯并（E）吲哚以及6-羟基-1,2,3,4-四氢苯并[F]喹啉衍生物，用于选择性癌症治疗 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130442672865.html">Novel prodrugs von 6-hydroxy-2,3-dihydro-1h-indoles, 5-hydroxy-1,2-dihydro-3h-pyrrolo3,2-eindoles and 5-hydroxy-1,2-dihydro-3h-benzo(e)indoles as well as of 6-hydroxy-1,2,3,4-tetrahydro-benzofquinoline derivatives for use in selective cancer therapy</a> <b>[P]</b> . <span> 外国专利：  US2004033962A1 </span> <span> . 2004-02-19</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：新型前药von 6-hydroxy-2,3-dihydro-1h-indoles，5-hydroxy-1,2-dihydro-3h-pyrrolo [3,2-e] indoles and 5-hydroxy-1,2-dihydro-3h -苯并（e）吲哚以及6-羟基-1,2,3,4-四氢-苯并[f]喹啉衍生物，用于选择性癌症治疗 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028161017','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> <h2>期刊订阅</h2> <img src="https://cdn.zhangqiaokeyan.com/img/loginclose.png" alt="关闭" onclick="$('.journalsub-pop-up').hide()"> <p class="pardon">抱歉，该期刊暂不可订阅，敬请期待！</p> <p 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