3,5-diphenyl-4H-1,2,6-thiadiazin-4-one | 1311147-78-0

• 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: 3,5-diphenyl-4H-1,2,6-thiadiazin-4-one
• 英文别名: 3,5-Diphenyl-1,2,6-thiadiazin-4-one；3,5-diphenyl-1,2,6-thiadiazin-4-one
• CAS: 1311147-78-0
• 化学式: C₁₅H₁₀N₂OS
• 分子量: 266.323
• InChiKey: LKUUJFCLEVTOQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 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：
  67.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl-4H-1,2,6-thiadiazin-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以97%的产率得到3,5-diphenyl-4H-1,2,6-thiadiazin-4-ol
  参考文献：
  名称：

  Substitution at C-4 in 3,5-disubstituted 4H-1,2,6-thiadiazin-4-ones

  摘要：

  3,5-Diaryl-4H-1,2,6-thiadiazin-4-ones react with NaBH4 to give the 3,5-diaryl-4H-1,2,6-thiadiazin-4-ols and with MeLi to give 4-methyl-3,5-diaryl-4H-1,2,6-thiadiazin-4-ols. The latter dehydrate with p-toluenesulfonic acid to give (3,5-diarylthiadiazin-4-ylidene)methanes. (3,5-Diphenyl-4H-1,2,6-thiadiazin-4-ylidene)methane 15 suffers mono bromination with NBS to give bromo(3,5-diphenyl-4H-1,2,6-thiadiazin-4-ylidene)methane 17. Dichloro- and dibromo(3,5-diphenyl-4H-1,2,6-thiadiazin-4-ylidene) methanes 18 and 19 are formed directly from the 3,5-diphenylthiadiazin-4-one 9 via the Appel reaction using Ph3P and CCl4 or CBr4, respectively. 3,5-Diarylthiadiazin-4-ones treated with P2S5 give 3,5-diarylthiadiazine-4-thiones that react with tetracyanoethylene oxide to give the (thiadiazin-4-ylidene) malononitriles. Finally, the 3,5-diphenylthiadiazine-4-thione 20 reacts with ethyl diazoacetate to give ethyl 2-(3,5-diphenyl-4H-1,2,6-thiadiazin-4-ylidene)acetate 26. The above reactions show that a variety of substitutions at C-4 of 3,5-diaryl substituted 1,2,6-thiadiazin-4-ones can be achieved, which extends the potential applications of this heterocycle. All compounds are fully characterized and a brief comparison of their spectroscopic properties is given. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.098
• 作为产物：
  描述：

  三丁基苯基锡 在 bis-triphenylphosphine-palladium(II) chloride 、 硫酸 作用下， 以 甲苯 为溶剂， 反应 1.58h， 生成 3,5-diphenyl-4H-1,2,6-thiadiazin-4-one
  参考文献：
  名称：

  3,5-二氯-4 H -1,2,6-噻二嗪4,4-缩酮的取代化学

  摘要：

  3,5-二氯-4 H -1,2,6-噻二嗪4,4-缩酮对C-3 / 5位置的亲核取代或钯催化的CC连接的反应性导致了七个新的3,5 -二取代4 H -1,2,6-噻二嗪乙二醇4,4-缩酮和七个3,5-二取代4 H -1,2,6-噻二嗪邻苯二酚4,4-缩酮，收率为83-98％。此外，成功地将3,5-二苯基-4 H -1,2,6-噻二嗪乙二醇和邻苯二酚4,4-缩酮成功地进行了水解。在20°C下使用H 2 SO 4，以74％和89％的产率得到3,5-二苯基-4 H -1,2,6-噻二嗪-4-one。

  DOI：

  10.1016/j.tetlet.2016.06.055

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。
• The Photochemical Mediated Ring Contraction of 4<i>H</i>-1,2,6-Thiadiazines To Afford 1,2,5-Thiadiazol-3(2<i>H</i>)-one 1-Oxides
  作者：Emmanouil Broumidis、Christopher G. Thomson、Brendan Gallagher、Lia Sotorríos、Kenneth G. McKendrick、Stuart A. Macgregor、Martin J. Paterson、Janet E. Lovett、Gareth O. Lloyd、Georgina M. Rosair、Andreas S. Kalogirou、Panayiotis A. Koutentis、Filipe Vilela

  DOI：10.1021/acs.orglett.3c02673

  日期：2023.9.22

  1,2,6-Thiadiazines treated with visible light and 3O2 under ambient conditions are converted into difficult-to-access 1,2,5-thiadiazole 1-oxides (35 examples, yields of 39–100%). Experimental and theoretical studies reveal that 1,2,6-thiadiazines act as triplet photosensitizers that produce 1O2 and then undergo a chemoselective [3 + 2] cycloaddition to give an endoperoxide that ring contracts with

  在环境条件下用可见光和3 O 2处理的 1,2,6-噻二嗪转化为难以获得的 1,2,5-噻二唑 1-氧化物（35 个例子，产率 39-100%）。实验和理论研究表明，1,2,6-噻二嗪作为三线态光敏剂，产生1 O 2，​​然后进行化学选择性 [3 + 2] 环加成，得到内过氧化物，该内过氧化物通过选择性碳原子切除和完整的原子经济而收缩。该反应在间歇和连续流动条件下进行了优化，并且在绿色溶剂中也很有效。
• Synthesis of <i>N</i>-Aryl-3,5-dichloro-4<i>H</i>-1,2,6-thiadiazin-4-imines from 3,4,4,5-Tetrachloro-4<i>H</i>-1,2,6-thiadiazine
  作者：Andreas S. Kalogirou、Maria Manoli、Panayiotis A. Koutentis

  DOI：10.1021/acs.orglett.5b02237

  日期：2015.8.21

  Condensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiacliazine with a range of anilines gave 22 N-aryl-3,5-dichloro-4H-1,2,6-thiadiazin-4-imines in 43-96% yields. The scope and limitations of this condensation are briefly investigated. Furthermore, mono- and bis-substitution of the C-3 and C-5 chlorines of 3,5-dichloro-N-phenyl-4H-1,2,6-thiadiazin-4-imine by amine and alkoxide nucleophiles is explored. Finally, Stille coupling chemistry is used to prepare several N-phenyl-3,5-diaryl-4H-1,2,6-thiadiazin-4-imines.
• 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.