3,5-di(fur-2-yl)-4H-1,2,6-thiadiazin-4-one | 1311147-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,5-di(fur-2-yl)-4H-1,2,6-thiadiazin-4-one
• 英文别名: 3,5-Bis(furan-2-yl)-1,2,6-thiadiazin-4-one；3,5-bis(furan-2-yl)-1,2,6-thiadiazin-4-one
• CAS: 1311147-74-6
• 化学式: C₁₁H₆N₂O₃S
• 分子量: 246.246
• InChiKey: OMJILOWPOMDZEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-di(fur-2-yl)-4H-1,2,6-thiadiazin-4-one 、 丙二腈 在 四氯化钛 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以84%的产率得到2-[3,5-di(fur-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]malononitril
  参考文献：
  名称：

  Synthesis of 2-(4H-1,2,6-thiadiazin-4-ylidene)malononitriles

  摘要：

  The base-free TiCl4-mediated condensation of 3,5-disubstituted-4H-1,2,6-thiadiazin-4-ones 8 with malononitrile affords 20 difficult to access (3,5-disubstituted-4H-1,2,6-thiadiazin-4-ylidene)malononitriles 7. The reaction tolerates 3,5-diaryl, diphenoxy, dimethoxy and diphenylthio substituted thiadiazinones, but not diamino, monohydroxy or dihalo substituents. Nevertheless, asymmetrically substituted 3-halo-5-phenyl- and 3-chloro-5-methoxy-4H-1,2,6-thiadiazin-4-ones convert into the corresponding ylide-nemalononitriles in good yield. Furthermore, the condensation works well with ethyl cyanoacetate and diethyl malonate, but not with Meldrum's acid, dimedone or nitromethane. Finally, 2-(3-chloro-5-phenyl-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (7q) reacts with aniline to give 4,7-diphenyl-6-(phenylimino)-6,7-dihydropyrrolo[2,3-c][1,2,6]thiadiazine-5-carbonitrile (12) in moderate yield demonstrating the potential use of these ylidenes to prepare novel 6-5 fused 4H-1,2,6-thiadiazines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.008
• 作为产物：
  描述：

  2-(三丁基锡烷基)呋喃 、 3,5-二氯-1,2,6-噻二嗪-4-酮 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以92%的产率得到3,5-di(fur-2-yl)-4H-1,2,6-thiadiazin-4-one
  参考文献：
  名称：

  Palladium Catalyzed C–C Coupling Reactions of 3,5-Dichloro-4H-1,2,6-thiadiazin-4-one

  摘要：

  Palladium catalyzed Suzuki-Miyaura, Stille, and Sonogashira coupling reactions are reported for the electron-deficient heterocyclic scaffold 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (1). Furthermore, 3,5-di(thien-2-yl)-4H-1,2,6-thiadiazin4-one (7m) is further elaborated to afford the tetrathienyl 3,5-bis[(2,2'-bithien)-5-yl]-4H-1,2,6-thiadiazin-4-one (9). All compounds are fully characterized.

  DOI：

  10.1021/ol201212b

文献信息

• The Acid and/or Thermal Mediated Ring Contraction of 4<i>H</i>-1,2,6-Thiadiazines To Afford 1,2,5-Thiadiazoles
  作者：Andreas S. Kalogirou、Andreas Kourtellaris、Panayiotis A. Koutentis

  DOI：10.1021/acs.orglett.6b01929

  日期：2016.8.19

  A near-quantitative acid and/or thermal mediated ring contraction of 3′,5′-diarylspiro(benzo[d][1,3]dioxole-2,4′-[1,2,6]thiadiazines) affords 3-aryl-4-(2-arylbenzo[d][1,3]dioxol-2-yl)-1,2,5-thiadiazoles. The reaction scope was studied providing 11 examples of this ring contraction. A double Wagner–Meerwein reaction mechanism is proposed.

  3'，5'-二芳基螺（苯并[ d ] [1,3]二恶唑-2,4'-[1,2,6]噻二嗪）的近定量酸和/或热介导的环收缩提供3-芳基-4-（2-芳基苯并[ d ] [1,3]二氧杂-2-基）-1,2,5-噻二唑。研究了反应范围，提供了该环收缩的11个实例。提出了双重Wagner-Meerwein反应机理。
• Palladium Catalyzed C–C Coupling Reactions of 3,5-Dichloro-4<i>H</i>-1,2,6-thiadiazin-4-one
  作者：Heraklidia A. Ioannidou、Christos Kizas、Panayiotis A. Koutentis

  DOI：10.1021/ol201212b

  日期：2011.7.1

  Palladium catalyzed Suzuki-Miyaura, Stille, and Sonogashira coupling reactions are reported for the electron-deficient heterocyclic scaffold 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (1). Furthermore, 3,5-di(thien-2-yl)-4H-1,2,6-thiadiazin4-one (7m) is further elaborated to afford the tetrathienyl 3,5-bis[(2,2'-bithien)-5-yl]-4H-1,2,6-thiadiazin-4-one (9). All compounds are fully characterized.
• Synthesis of 2-(4H-1,2,6-thiadiazin-4-ylidene)malononitriles
  作者：Andreas S. Kalogirou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2014.09.008

  日期：2014.11

  The base-free TiCl4-mediated condensation of 3,5-disubstituted-4H-1,2,6-thiadiazin-4-ones 8 with malononitrile affords 20 difficult to access (3,5-disubstituted-4H-1,2,6-thiadiazin-4-ylidene)malononitriles 7. The reaction tolerates 3,5-diaryl, diphenoxy, dimethoxy and diphenylthio substituted thiadiazinones, but not diamino, monohydroxy or dihalo substituents. Nevertheless, asymmetrically substituted 3-halo-5-phenyl- and 3-chloro-5-methoxy-4H-1,2,6-thiadiazin-4-ones convert into the corresponding ylide-nemalononitriles in good yield. Furthermore, the condensation works well with ethyl cyanoacetate and diethyl malonate, but not with Meldrum's acid, dimedone or nitromethane. Finally, 2-(3-chloro-5-phenyl-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (7q) reacts with aniline to give 4,7-diphenyl-6-(phenylimino)-6,7-dihydropyrrolo[2,3-c][1,2,6]thiadiazine-5-carbonitrile (12) in moderate yield demonstrating the potential use of these ylidenes to prepare novel 6-5 fused 4H-1,2,6-thiadiazines. (C) 2014 Elsevier Ltd. All rights reserved.