3-(phenylthio)-2-(thiophen-2-yl)-1H-indole | 1213786-09-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylthio)-2-(thiophen-2-yl)-1H-indole
• 英文别名: 3-phenylsulfanyl-2-thiophen-2-yl-1H-indole
• CAS: 1213786-09-4
• 化学式: C₁₈H₁₃NS₂
• 分子量: 307.44
• InChiKey: MTNMLUFEXCIGHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(thiophen-2-ylethynyl)aniline 、 苯磺酰肼 在 碘 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以77%的产率得到3-(phenylthio)-2-(thiophen-2-yl)-1H-indole
  参考文献：
  名称：

  Microwave assisted metal-/oxidant-free cascade electrophilic sulfenylation/5-endo-dig cyclization of 2-alkynylanilines to generate diversified 3-sulfenylindoles

  摘要：

  A metal-/oxidant-free sustainable protocol for the synthesis of 3-sulfenylindoles based on electrophilic cyclization of 2-alkynylanilines has been developed under microwave irradiation. Herein, catalytic amount of iodine and stoichiometric amount of sulfonyl hydrazides were employed as catalyst and electrophiles respectively to induce the 5-endo-dig cyclization of 2-alkynylanilines. This strategy allows a wide substrate scope, demonstrates good functional group tolerance, utilizes easily available reagents and overcome multistep synthesis. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.08.046

文献信息

• Palladium-Catalyzed Annulation of 2-(1-Alkynyl)benzenamines with Disulfides: Synthesis of 3-Sulfenylindoles
  作者：Yan-Jin Guo、Ri-Yuan Tang、Jin-Heng Li、Ping Zhong、Xing-Guo Zhang

  DOI：10.1002/adsc.200900055

  日期：2009.11

  3-Sulfenylindoles can be efficiently prepared in moderate to good yields from 2-(1-alkynyl)benzenamines and disulfides using the palladium/air catalytic systems. The study also provides a useful route to the synthesis of fipronil analogues.

  使用钯/空气催化系统，可以由2-（1-炔基）苯胺和二硫化物有效地以中等到良好的产率制备3-亚磺酰基吲哚。该研究还提供了合成氟虫腈类似物的有用途径。
• Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts as <i>S</i>-arylation sources
  作者：Jianxiao Li、Hao Tang、Zidong Lin、Shaorong Yang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/d0ob00828a

  日期：——

  A novel and efficient palladium-catalyzed three-component cascade cyclization/arylthiolation has been developed for the assembly of diverse 3-sulfenylindole and 3-sulfenylbenzofuran derivatives from 2-alkynylamines and 2-alkynylphenols, aryldiazonium salts, and Na2S2O3 under aerobic conditions with PEG-200 as an environmentally benign medium. The current study features exceptional functional group

  一种新颖的和有效的钯催化的三组分级联环化/ arylthiolation已经开发了用于装配多样3- sulfenylindole并从2-炔基胺和2- alkynylphenols，芳基重氮盐，和Na 3-sulfenylbenzofuran衍生物的2小号2 ö 3下PEG-200作为环境友好介质的有氧条件。当前的研究具有卓越的官能团耐受性，而无需额外的配体，氧化剂或银盐，并且环保型反应条件温和。离子液体[C 2 OHmim] Cl作为环保添加剂在该协议中起着至关重要的作用。值得注意的是，该方法代表了使用芳基重氮盐作为直接S的第一个例子这种化学转化中的芳基化来源。
• Microwave assisted metal-/oxidant-free cascade electrophilic sulfenylation/5-endo-dig cyclization of 2-alkynylanilines to generate diversified 3-sulfenylindoles
  作者：Shivani Sharma、Ramdas S. Pathare、Sukanya、Antim K. Maurya、Bhagyashree Goswami、Vijai K. Agnihotri、Devesh M. Sawant、Ram T. Pardasani

  DOI：10.1016/j.tetlet.2017.08.046

  日期：2017.10

  A metal-/oxidant-free sustainable protocol for the synthesis of 3-sulfenylindoles based on electrophilic cyclization of 2-alkynylanilines has been developed under microwave irradiation. Herein, catalytic amount of iodine and stoichiometric amount of sulfonyl hydrazides were employed as catalyst and electrophiles respectively to induce the 5-endo-dig cyclization of 2-alkynylanilines. This strategy allows a wide substrate scope, demonstrates good functional group tolerance, utilizes easily available reagents and overcome multistep synthesis. (C) 2017 Elsevier Ltd. All rights reserved.