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A Straightforward One‐Step Access to Ticlopidine Derivatives Arylated at the C5‐Position of the Thienyl Ring via Pd‐Catalyzed Direct Arylations

机译:通过PD催化的直接芳基,对噻吩基环的C5位置施加在噻吩基环的C5位置的直接一步进入

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Abstract > The reactivity of Ticlopidine, which belongs to the thienopyridine drug family, in Pd‐catalyzed C?H bond functionalization was investigated. The use of a palladium‐diphosphine catalyst associated to potassium acetate base in N , N ‐dimethylacetamide was found to promote the regioselective arylation at the C5‐position of the Ticlopidine thienyl ring with aryl bromides in high yields. In the course of this reaction, no dechlorination or debenzylation of the 2‐chlorobenzyl group of Ticlopidine was observed. A wide variety of substituents on the aryl bromide was tolerated, such as nitro, nitrile, acetyl, propionyl, benzoyl, ester, chloro, fluoro or trifluoromethyl. Bromopyridines and bromoquinolines were also successfully employed. This methodology gives a one‐step access to arylated Ticlopidine derivatives from commercially available compounds via a straightforward C?H bond functionalization procedure. Therefore, it provides a very appealing method to build a library of compounds containing a Ticlopidine unit. </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> > 研究了属于噻吩吡啶药物的噻氯丙胺的反应性,PD催化的C-H键官能化。使用与醋酸钾基础相关的钯 - 二膦催化剂 n </ i> 那 n </ i> - 发现 - 甲基乙酰胺在高产率高的芳基溴化物的C5-位置促进在噻吩甲基噻吩基环的C5位置处的区域选择性浓缩。在该反应过程中,观察到噻氯丙基的2-氯苄基的脱氯或脱苄酰基化。耐受芳基溴的各种取代基,例如硝基,腈,乙酰基,丙酰基,苯并,酯,氯,氟或三氟甲基。也成功地使用了溴吡啶和溴喹啉。该方法通过直接的C-H键官能化方法给出了从市售化合物的仲成噻吩啉衍生物的一步进入。因此,它提供了一种非常有吸引力的方法,用于构建含有噻吩啉单位的化合物库。 </ 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-19765/'>《Asian Journal of Organic Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2019年第11期</span><b style="margin: 0 2px;">|</b><span>共7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=Atoui Dhieb&option=202" target="_blank" rel="nofollow">Atoui Dhieb;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Haoran&option=202" target="_blank" rel="nofollow">Li Haoran;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ben Salem Ridha&option=202" target="_blank" rel="nofollow">Ben Salem Ridha;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Roisnel Thierry&option=202" target="_blank" rel="nofollow">Roisnel Thierry;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Soulé Jean‐Fran?ois&option=202" target="_blank" rel="nofollow">Soulé Jean‐Fran?ois;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Doucet Henri&option=202" target="_blank" rel="nofollow">Doucet Henri;</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>CNRS ISCR-UMR 6226Univ RennesF-35000 Rennes France;</p> <p>CNRS ISCR-UMR 6226Univ RennesF-35000 Rennes France;</p> <p>Laboratoire de Chimie Organique LR 17ES08 Faculté des Sciences de SfaxUniversité de SfaxBP 1171 Route de la Soukra km 4 3038 Sfax Tunisia;</p> <p>CNRS ISCR-UMR 6226Univ RennesF-35000 Rennes France;</p> <p>CNRS ISCR-UMR 6226Univ RennesF-35000 Rennes France;</p> <p>CNRS ISCR-UMR 6226Univ RennesF-35000 Rennes France;</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/1184.html" title="有机化学">有机化学;</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=catalysis&option=203" rel="nofollow">catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=palladium&option=203" rel="nofollow">palladium;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=C?H bond functionalization&option=203" rel="nofollow">C?H bond functionalization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ticlopidine&option=203" rel="nofollow">Ticlopidine;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=arylation&option=203" rel="nofollow">arylation;</a> </p> <div class="translation"> 机译:催化;钯;C?H键官能化;噻丙酯;芳己; </div> </li> <li> <span class="lefttit">入库时间</span> <span>2022-08-20 01:29:16</span> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704022773556.html">A Straightforward One‐Step Access to Ticlopidine Derivatives Arylated at the C5‐Position of the Thienyl Ring via Pd‐Catalyzed Direct Arylations</a> <b>[J]</b> . <span> <a 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class="tuijian_authcolor"> . 有机化学 </a> </span> <span> . 2009</span><span>,第6期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-67038_thesis/020223029822.html">环八四噻吩及其芳基化与树枝状衍生物的AIE现象</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=杨玉杰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 杨玉杰</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=赵春梅&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,赵春梅</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王鹏飞&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王鹏飞</a> <span> <a href="/conference-cn-67038/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 全国第十九届大环化学暨第十一届超分子化学学术讨论会 </a> <span> <span> . 2018</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020316246719.html">基于噻吩/硒吩基并三芳杂环的非对称有机半导体材料及“S”型双螺烯的合成</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王萌杰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王萌杰</a> <span> . 2020</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120106457984.html">6-环氨基-2-噻吩基-3-(吡啶-4-基)咪唑并1,2-b哒嗪和6-环氨基-2-呋喃基-3-(吡啶-4-基)咪唑并1,2-b哒嗪的衍生物,其制备和治疗用途</a> <b>[P]</b> . <span> 中国专利: CN102256979A </span> <span> . 2011-11-23</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120107447491.html">取代的1-(芳基乙炔基)双环链烷醇、1-(杂芳基乙炔基)双环链烷醇、1-(杂环基乙炔基)双环链烷醇和1-(环烯基乙炔基)双环链烷醇作为对抗非生物植物胁迫的活性剂的用途</a> <b>[P]</b> . <span> 中国专利: CN104955327A </span> <span> . 2015-09-30</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130499563632.html">SYNTHESIS OF FT4-BASED ORGANIC SEMICONDUCTING SMALL MOLECULES BY PD-CATALYZED DIRECT (HETERO)ARYLATION OR DIRECT ALKENYLATION</a> <b>[P]</b> . <span> 外国专利: <!-- --> US2021074930A1 </span> <span> . 2021-03-11</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:通过PD催化直接(杂)芳基化或直接链烯化合成FT4基有机半导体小分子 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130446737613.html">Process for the one-step direct alkylation, in positions 7 and 10 simultaneously of the two hydroxy functions on 10-deacetylbaccatin (of the taxoid family) or on derivatives thereof which are esterified in position 13</a> <b>[P]</b> . <span> 外国专利: <!-- --> NZ504125A </span> <span> . 2002-10-25</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:在10-去乙酰基浆果赤霉素(紫杉烷类)或其衍生物上在13位酯化的两个羟基官能团同时在7和10位进行一步一步直接烷基化的方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130450887640.html">Direct alkylation process, in a single step, in position 7 and 10 simultaneously of the two hydroxyl functions of 10-deacetylbaccatin or derivatives of the latter in position 13</a> <b>[P]</b> . <span> 外国专利: <!-- --> BR9814658A </span> <span> . 2000-10-03</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:在10位脱乙酰浆果赤霉素或其衍生物在13位的两个羟基官能团同时在7位和10位进行直接烷基化过程 </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;" > 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