N-(2-pyridyl)-N'-p-tolylthiourea | 27429-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-pyridyl)-N'-p-tolylthiourea
• 英文别名: 1-(4-Methylphenyl)-3-pyridin-2-ylthiourea
• CAS: 27429-31-8
• 化学式: C₁₃H₁₃N₃S
• 分子量: 243.332
• InChiKey: PJFSGFRBLPNHHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-pyridyl)-N'-p-tolylthiourea 生成 sodium;N-(4-methylphenyl)-N'-pyridin-2-ylcarbamimidothioate
  参考文献：
  名称：

  PRASAD C. S. G.; TANEJA A. D.; BANERJI S. K., REV. ROUM. CHIM. , 1975, 20, NO 1, 115-120

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基吡啶 以65%的产率得到
  参考文献：
  名称：

  GUPTA R. C.; NATH R.; SHANKER K.; BHARGAVA K. P.; KISHOR K., J. INDIAN CHEM. SOC., 1978, 55, NO 8, 832-834

  摘要：

  DOI：

文献信息

• Hypervalent Iodine(III)-Mediated Solvent-Free, Regioselective Synthesis of 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles and 2-Aminobenzo[<i>d</i> ]thiazoles
  作者：Nagaraju Tumula、Radha Krishna Palakodety、Sridhar Balasubramanian、Mangarao Nakka

  DOI：10.1002/adsc.201800353

  日期：2018.8.6

  A convenient approach for the synthesis of 3,4‐disubstituted 5‐imino‐1,2,4‐thiadiazoles and 2‐aminobenzo[d]thiazoles has been developed using phenyliodine diacetate (PIDA). This approach involves a metal‐free oxidative C−N, N−S and C−S bond formations under neat conditions. High regioselectivity, solvent‐free conditions, short reaction time and broad functional group compatibility are the notable features

  使用苯基乙酸二乙酸酯（PIDA）已开发出一种方便的合成3,4-二取代的5-亚氨基-1,2,4-噻二唑和2-氨基苯并[ d ]噻唑的方法。该方法涉及在纯净条件下形成无金属的氧化性C-N，N-S和C-S键。高区域选择性，无溶剂条件，较短的反应时间和广泛的官能团相容性是本报告的显着特征。
• Hypervalent Iodine Promoted Regioselective Oxidative C-H Functionalization: Synthesis of<i>N</i>-(Pyridin-2-yl)benzo[<i>d</i>]thi­azol-2-amines
  作者：Arumugam Mariappan、Kandasamy Rajaguru、Somi Santharam Roja、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1002/ejoc.201501202

  日期：2016.1

  Biologically potent N-(pyridin-2-yl)benzo[d]thiazol-2-amines were conveniently synthesized from simple heteroaryl-thioureas through an oxidative C–S bond formation strategy that employed phenyliodine(III) bis(trifluoroacetate) as the oxidant. This protocol features a metal-free approach, a broad scope of substrates, short reaction times, and a simple product purification procedure.

  通过使用苯基碘（III）双（三氟乙酸盐）作为氧化剂的氧化 C-S 键形成策略，从简单的杂芳基硫脲方便地合成了具有生物活性的 N-（吡啶-2-基）苯并[d]噻唑-2-胺. 该协议具有无金属方法、广泛的底物、较短的反应时间和简单的产品纯化程序。
• Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules
  作者：Ananya Anubhav Saikia、Ramdas Nishanth Rao、Barnali Maiti、Musuvathi Motilal Balamurali、Kaushik Chanda

  DOI：10.1021/acscombsci.0c00083

  日期：2020.11.9

  2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates followed by base catalyzed ring closure with 1,2-dibromoethane to obtain thiazolidine-2-imines with broad substrate scope and high functional group tolerance. The synthetic strategy merges well with the thiourea formation followed by base catalyzed ring closure reaction for the thiazolidine-2-imine synthesis in a more modular and straightforward

  在这项工作中，描述了一种用于 thiazolidine-2-亚胺组合库的单锅伸缩方法。通过2-氨基吡啶/吡嗪/嘧啶与取代的异硫氰酸酯反应，然后用1,2-二溴乙烷进行碱催化闭环，合成操作顺利进行，得到具有广泛底物范围和高官能团耐受性的噻唑烷-2-亚胺。合成策略与硫脲形成很好地结合，然后以更模块化和更直接的方法合成噻唑烷-2-亚胺的碱催化闭环反应。与传统方法相比，本文报道的合成程序代表了一种更清洁的 thiazolidine-2-亚胺路线。而且，
• Anticonvulsant activity and succinate dehydrogenase inhibitory property of new substituted thiobarbiturates
  作者：Anjali Dhasmana、J. P. Barthwal、B. R. Pandey、B. Ali、K. P. Bhargava、S. S. Parmar

  DOI：10.1002/jhet.5570180341

  日期：1981.5

  Eight 1-aryl-3-(2-pyridyl)thiobarbiturates were synthesized and evaluated for their anticonvulsant property and their ability to inhibit succinate dehydrogenase activity of rat brain homogenates. These substituted thiobarbiturates (100 mg./kg., i.p.) provided 20–60% protection against pentylenetetrazol-induced convulsions in albino mice. Low toxicity of these compounds was reflected by their high approximate

  合成了八种1-芳基-3-（2-吡啶基）硫代巴比妥酸酯，并评估了它们的抗惊厥性质以及它们抑制大鼠脑匀浆中琥珀酸脱氢酶活性的能力。这些取代的硫代巴比妥酸酯（100 mg./kg。，腹腔注射）在白化病小鼠中提供了20-60％的保护，防止戊四氮诱发的惊厥。这些化合物的低毒性通过其较高的大约LD 50值反映出来，该值在500-1000 mg./kg的范围内。所有取代的硫代巴比妥酸酯（Im M）均可抑制体外琥珀酸脱氢酶的活性，其抑制程度为10％至72％。
• <i>N</i>-Iodosuccinimide mediated intramolecular oxidative C(<i>sp</i>²)-S bond formation for the synthesis of 2-aminobenzothiazole derivatives
  作者：Atul A. Jichkar、Imran A. Opai、Nandkishor N. Karade

  DOI：10.1080/17415993.2021.1989436

  日期：2022.3.4

  An extremely efficient synthetic method for the preparation of 2-aminobenzothiazole derivatives starting from arylthioureas by using N-iodosuccinimide has been reported. This protocol features a mild reaction conditions, a short reaction time, and metal-free oxidative conditions for C (sp2)-S bond construction.

  报道了一种使用N-碘代琥珀酰亚胺以芳基硫脲为原料制备 2-氨基苯并噻唑衍生物的极其有效的合成方法。该方案具有反应条件温和、反应时间短、C ( sp 2 )-S 键构建的无金属氧化条件等特点。