3-(4-chlorophenyl)-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide | 40018-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 3-(4-chlorophenyl)-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide
• 英文别名: 3-(4-Chlorophenyl)-2H-1,2,4-benzothiadiazine-1,1-dioxide；3-(4-chlorophenyl)-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 40018-40-4
• 化学式: C₁₃H₉ClN₂O₂S
• 分子量: 292.746
• InChiKey: XFIPWMOECLBLOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 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：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 、 4-碘甲苯 在 silver(I) acetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 以68%的产率得到3-(5-chloro-4'-methylbiphenyl-2-yl)-2H-benzo[1,2,4]thiadiazine 1,1-dioxide
  参考文献：
  名称：

  3-芳基-2 H-苯并[1,2,4]噻二嗪1,1-二氧化物的钯催化直接CH芳基化：合成苯并噻二嗪-1,1-二氧化物衍生物的有效策略†

  摘要：

  描述了一种新的钯催化的C（sp 2）-H键的苯并噻二嗪-1,1-二氧化物直接芳基化。3-芳基-2 H-苯并[1,2,4]噻二嗪1,1-二氧化物与各种芳基碘反应生成相应的单芳基化产物3-（联苯基-2-基）-2 H-苯并[1 ，2,4]噻二嗪1,1-二氧化物在AgOAc存在下具有高反应活性和区域选择性。值得注意的是，添加TFA对于提高芳基化收率至关重要。

  DOI：

  10.1039/c5ob02196k
• 作为产物：
  描述：

  2-(4-chlorobenzylamino)benzenesulfonamide 在 dipotassium peroxodisulfate 作用下， 以 乙腈 为溶剂， 以72%的产率得到3-(4-chlorophenyl)-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide
  参考文献：
  名称：

  Sulfate Radical Anion (SO₄^•–) Mediated C(sp³)–H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

  摘要：

  A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.

  DOI：

  10.1021/acs.joc.5b01872

文献信息

• Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes
  作者：Muhammad Sharif、Julita Opalach、Peter Langer、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c3ra45765f

  日期：——

  An interesting procedure for the zinc-catalyzed oxidative transformation of ready available 2-aminobenzamide, 2-aminobenzenesulfonamide with benzyl alcohols has been developed. Various quinazolinones and benzothiadiazine 1,1-dioxides were prepared in moderate to good yields under identical conditions. The reactions of both aromatic aldehydes and aliphatic aldehydes with 2-aminobenzamide under catalyst free conditions were described as well. In water media, the products were formed in good yields.

  开发了一种有趣的过程，用于锌催化氧化转化易于获得的2-氨基苯甲酰胺和2-氨基苯磺酰胺与苄醇。在相同条件下，制备了各种喹唉酮和苯并噻二嗪1,1-二氧化物，产率中等至良好。此外，还描述了在无催化剂条件下，2-氨基苯甲酰胺与芳香醛和脂肪醛的反应。在水介质中，产物形成良好产率。
• Metal-free sequential dual oxidative amination of C(sp³)–H bonds: A direct approach to benzothiadiazine 1,1-dioxide derivatives
  作者：Dongyin Wang、Xiaokang Li、Yongli Zhao、Junmin Chen

  DOI：10.1080/00397911.2016.1265128

  日期：2017.2.16

  ABSTRACT An efficient and metal-free Di-tert-butyl peroxide (DTBP)-promoted dual oxidative amination annulation of 2-amino arylsulfonamide with methylarene has been developed. This protocol provides straightforward access to benzothiadiazine 1,1-dioxide derivatives without using prefunctionalized substrates in good to excellent yields with good functional group tolerance. GRAPHICAL ABSTRACT

  摘要开发了一种高效且无金属的二叔丁基过氧化物 (DTBP) 促进的 2-氨基芳基磺酰胺与甲基芳烃的双重氧化胺化环化。该协议提供了对苯并噻二嗪 1,1-二氧化物衍生物的直接访问，而无需使用具有良好官能团耐受性的良好至极好的产量的预官能化底物。图形概要
• Wang-OSO3H catalyzed one-pot sonochemical synthesis of 1,2,4-benzothiadiazine-1,1-dioxide derivatives: Their in silico / in vitro assessments against MtbCM
  作者：Narender Addu、Hinuja Miriyala、Ravikumar Kapavarapu、Sunder Kumar Kolli、Manojit Pal

  DOI：10.1016/j.molstruc.2023.135313

  日期：2023.7

  yields. The use of heterogeneous catalyst, common oxidant, water as a solvent and ultrasound as the source of green energy in addition to the mild conditions, shorter reaction time and simple operational procedure are the key features of this methodology. In silico studies suggested that most of the synthesized compounds interacted with the external surface pockets of the MtbCM (PDB: 2FP2) active site cavity

  描述了一系列 1,2,4-苯并噻二嗪-1,1-二氧化物衍生物的声化学合成、计算机评估和体外Mtb CM 抑制活性。这些化合物是通过一锅两步声化学方法合成的，该方法涉及 Wang-OSO 3 H 催化 2-氨基苯磺酰胺与醛的反应，然后用 NaHSO 3处理在同一个锅里。反应在室温下在纯水中进行，以良好的产率提供所需产物。使用非均相催化剂、普通氧化剂、水作为溶剂和超声波作为绿色能源以及温和的条件、较短的反应时间和简单的操作程序是该方法的主要特点。计算机研究表明，大多数合成化合物与Mtb CM（PDB：2FP2）活性位点腔的外表面袋相互作用。事实上，在这些化合物结合和对齐的地方注意到了一个弯曲的环位点。三种化合物如3c 、3d和3e通过-NHSO 2 - 它们的 2 H -benzo[ e ][1,2,4]thiadiazine-1,1-dioxide 环的部分显示出与 SER70 的共同 H 键。当以
• Derivation of Benzothiadiazine‐1,1‐dioxide Scaffolds via Transition Metal‐Catalyzed C—H Activation/Annulation
  作者：Ruizhi Lai、Shuran Xu、Qingyao Zhang、Hui Zhou、Cankun Luo、Yuerong Wang、Li Hai、Yong Wu

  DOI：10.1002/cjoc.202300095

  日期：2023.8.15

  Benzothiadiazine-1,1-dioxide scaffold is bioactive framework with wild utility and applications. Synthesis of benzothiadiazine-fused isoquinoline derivatives and spiro benzothiadiazine derivatives through transition metal-catalyzed C—H activation/annulation was reported. 3-Phenyl-2H-benzothiadiazine-1,1-dioxide was used as the reaction substrate, and vinylene carbonate and 4-diazopyrazolone were used as the coupling

  1,1-二氧化苯并噻二嗪支架是具有广泛用途和应用的生物活性框架。报道了通过过渡金属催化的CH活化/环化合成苯并噻二嗪稠合异喹啉衍生物和螺环苯并噻二嗪衍生物。以3-苯基-2H-苯并噻二嗪-1,1-二氧化物为反应底物，碳酸亚乙烯酯和4-二氮杂吡唑酮分别为偶联剂。该策略提供了以高效且简单的方式直接获取复杂的N-杂环的方法。
• Rh(III)‐Catalyzed C−H Annulation of 3‐Aryl‐2<i>H</i>‐benzo[<i>e</i>][1,2,4]thiadiazine‐1,1‐dioxides with Vinylene Carbonates
  作者：Chaitanya Ittamalla、D.Yogananda Chary、Sridhar Balasubramanian、B. V. Subba Reddy

  DOI：10.1002/ejoc.202300983

  日期：2024.1.22

  A novel method has been developed for the synthesis of fused dihydroisoquinoline frameworks through a Rh(III)‐catalyzed annulation of 3‐aryl‐2H‐benzo[e][1,2,4]thiadiazine‐1,1‐dioxides with vinylene carbonates by C−H bond activation. This is the first report on the oxidative C−H functionalization of aryl‐2H‐benzo[e][1,2,4]thiadiazine‐1,1‐dioxide with vinylene carbonate to afford angularly fused heterocycles in good yields with high functional group tolerance. In this approach, vinylene carbonate acts as a glycolaldehyde surrogate to construct the fused dihydroisoquinoline ring systems.

  摘要 通过Rh(III)催化3-芳基-2H-苯并[e][1,2,4]噻二嗪-1,1-二氧化物与碳酸乙烯酯的C-H键活化，开发了一种合成融合二氢异喹啉框架的新方法。这是首次报道芳基-2H-苯并[e][1,2,4]噻二嗪-1,1-二氧化物与碳酸亚乙烯酯进行 C-H 键氧化官能化，从而以良好的产率和较高的官能团耐受性得到角融合杂环。在这种方法中，碳酸亚乙烯酯作为乙醛代用品构建了融合的二氢异喹啉环系统。