2-吡咯-1-基-1,3-苯并噻唑 | 383142-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-吡咯-1-基-1,3-苯并噻唑
• 英文名称: 2-(1H-pyrrol-1-yl)benzo[d]thiazole
• 英文别名: 2-pyrrol-1-yl-1,3-benzothiazole
• CAS: 383142-27-6
• 化学式: C₁₁H₈N₂S
• mdl: MFCD02665504
• 分子量: 200.264
• InChiKey: XXHJABOPNDFQDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯并噻唑 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-吡咯-1-基-1,3-苯并噻唑
  参考文献：
  名称：

  通过噻唑-2-基鏻中间体对苯并噻唑进行 CH 官能化。

  摘要：

  苯并噻唑与三苯基膦进行区域选择性 C2-H 官能化形成噻唑-2-基-三苯基鏻盐，这些鏻盐与多种 O 和 N 中心亲核试剂反应生成相应的醚、胺和 CN 联芳基。反应在温和条件下进行，并允许在序列末端回收三苯膦。在氢氧化物存在下，鏻盐发生歧化反应，导致苯并噻唑还原，这可用于苯并噻唑的特定 C2 氘化。

  DOI：

  10.1021/acs.orglett.0c00882

文献信息

• A <scp>solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas</scp> protocol for the synthesis of <scp>N‐aryl</scp> pyrroles under microwave irradiation
  作者：Kizhakkekuttu Radhakrishnan Rohit、Gopinadh Meera、Gopinathan Anilkumar

  DOI：10.1002/jhet.4372

  日期：2022.1

  reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction

  已经开发了第一个使用 2,5-二甲氧基四氢呋喃与各种取代的芳族胺合成 N-取代吡咯的锰催化改性 Clauson-Kaas 反应（产率高达 89%）。这种有趣的简洁策略不含添加剂，包括助催化剂、配体和酸。在微波条件下，使用成本相对较低、环境友好、方便的Mn(NO 3 ) 2 ·4H 2 O作为催化剂，反应时间非常短（20分钟）。上述品质证明了这种反应的绿色性质。
• Synthesis of C,N′-linked bis-heterocycles using a deprotometalation–iodination–N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells
  作者：Madani Hedidi、Ghenia Bentabed-Ababsa、Aïcha Derdour、Thierry Roisnel、Vincent Dorcet、Floris Chevallier、Laurent Picot、Valérie Thiéry、Florence Mongin

  DOI：10.1016/j.bmc.2014.04.028

  日期：2014.7

  crude iodides were involved in the N-arylation of pyrrole, indole, carbazole, pyrazole, indazole, imidazole and benzimidazole in the presence of Cu (0.2 equiv) and Cs2CO3 (2 equiv), and using acetonitrile as solvent (no other ligand) to provide after 24 h reflux the expected N-arylated azoles in yields ranging from 33% to 81%. Using benzotriazole also led to N-arylation products, but in lower 34%, 39%

  苯并噻吩，苯并呋喃，苯并噻唑和苯并恶唑是使用由ZnCl 2 ·TMEDA（TMEDA =  N，N，N '，N'-四甲基乙二胺，1当量）和2,2,6,6-四甲基哌啶锂制备的锂-锌组合脱金属金属盐的。（LiTMP，3当量）。随后使用碘作为亲电试剂拦截2-金属化衍生物，碘化物的收率分别为81％，82％，67％和42％。与使用ZnCl 2获得的产率相比，这些产率更高（提高了10％）·TMEDA（0.5当量）和LiTMP（1.5当量），但苯并恶唑（少10％）的情况除外。在Cu（0.2当量）和Cs 2 CO 3存在下，粗碘化物参与吡咯，吲哚，咔唑，吡唑，吲唑，咪唑和苯并咪唑的N-芳基化反应（2当量），并使用乙腈作为溶剂（无其他配体），在回流24小时后提供预期的N-芳基化吡咯，产率为33％至81％。使用苯并三唑还可以产生N-芳基化产物，但产率分别较低，分别为34％，39％，36％和6％。对该唑的进一步研究证明了2
• A General C–N Cross-Coupling to Synthesize Heteroaryl Amines Using a Palladacyclic N-Heterocyclic Carbene Precatalyst
  作者：Ruoqian Fan、Meiying Kuai、Dong Lin、Felix Bauer、Weiwei Fang

  DOI：10.1021/acs.orglett.2c03580

  日期：2022.12.2

  6-diisopropylphenyl)acenaphthoimidazol-2-ylidene (AnIPr) with an achiral 2-naphthyl-4,4-dimethyloxazoline palladacyclic fragment. Applying this precatalyst enabled a general protocol for Pd-catalyzed C–N cross-coupling reactions of challenging five- or six-membered ring heteroaryl chlorides and various heterocyclic amines. The desired aminated products, including commercial pharmaceuticals or key intermediates such

  通过将 1,3-双(2,6-二异丙基苯基)苊并咪唑-2-亚基 (AnIPr) 与非手性 2-萘基-4,4-二甲基恶唑啉钯环片段结合，设计了一种新型钯环 N-杂环卡宾预催化剂。应用这种预催化剂可以实现具有挑战性的五元或六元环杂芳基氯和各种杂环胺的 Pd 催化 C-N 交叉偶联反应的通用方案。理想的胺化产品，包括商业药物或关键中间体，如吡贝地尔、嘧菌环胺、V600E BRAF 抑制剂、曲苯那敏、517-β-羟基类固醇脱氢酶抑制剂、brexpipRAzole 和 sonidegib，实现了良好至优异的收率（>61 例，≤99 % 产量）。
• Buchwald‐Hartwig Amination of Coordinating Heterocycles Enabled by Large‐but‐Flexible Pd‐BIAN‐NHC Catalysts**
  作者：Dong‐Hui Li、Xiao‐Bing Lan、A‐Xiang Song、Md. Mahbubur Rahman、Chang Xu、Fei‐Dong Huang、Roman Szostak、Michal Szostak、Feng‐Shou Liu

  DOI：10.1002/chem.202103341

  日期：2022.1.19

  AbstractA new class of large‐but‐flexible Pd‐BIAN‐NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N‐heterocyclic carbene) has been rationally designed to enable the challenging Buchwald‐Hartwig amination of coordinating heterocycles. This robust class of BIAN‐NHC catalysts permits cross‐coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron‐deficient heterocycles containing multiple heteroatoms with BIAN‐INon (N,N′‐bis(2,6‐di(4‐heptyl)phenyl)‐7H‐acenaphtho[1,2‐d]imidazol‐8‐ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN‐NHC scaffold.
• Synthesis of 2-N-substituted benzothiazoles via domino condensation-hetero cyclization process, mediated by copper oxide nanoparticles under ligand-free conditions
  作者：G. Satish、K. Harsha Vardhan Reddy、K. Ramesh、K. Karnakar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2012.03.012

  日期：2012.5

  A simple and highly practical method for the synthesis of 2-N-substituted benzothiazoles has been developed by using nanocopper oxide as a recyclable catalyst. The present tandem process allows to get access to a wide range of 2-N-substituted benzothiazoles in good to excellent yields by the reaction of 2-iodo aniline with carbon disulfide and piperidine in presence of KOH as a base and DMSO as a solvent under ligand-free conditions. (C) 2012 Elsevier Ltd. All rights reserved.