pyridine-2-aldehyde tosylhydrazone | 22353-29-3

• 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: pyridine-2-aldehyde tosylhydrazone
• 英文别名: pyridinecarbaldehyde tosylhydrazone；2-pyridinetosylhydrazone；4-methyl-N'-(pyridin-2-ylmethylene)benzenesulfonohydrazide；2-pyridinecarboxaldehyde tosylhydrazone；4-methyl-N-(pyridin-2-ylmethylideneamino)benzenesulfonamide
• CAS: 22353-29-3
• 化学式: C₁₃H₁₃N₃O₂S
• 分子量: 275.331
• InChiKey: BONWWPOKZVRKEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pyridine-2-aldehyde tosylhydrazone 在 吗啉 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 生成 2-二溴甲基吡啶
  参考文献：
  名称：

  1,2,3-三唑并[1,5- a ]吡啶与亲电试剂的反应

  摘要：

  用氯，溴或乙酸汞的三唑并[1,5- a ]吡啶（1）处理时，得到二氯甲基，二溴甲基和烷氧基（烷氧基汞）甲基吡啶（3），（4），（5）和（8）含氮损失。硝化得到3-硝基三唑并吡啶（9），还原后得到3-（2-吡啶基）咪唑并[1，5- a ]吡啶（11）。讨论了这些化合物的形成机理。

  DOI：

  10.1039/p19810000078
• 作为产物：
  描述：

  对甲苯磺酰氯 在 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 pyridine-2-aldehyde tosylhydrazone
  参考文献：
  名称：

  Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

  摘要：

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.040

文献信息

• Ni-Catalyzed Alkenylation of Triazolopyridines: Synthesis of 2,6-Disubstituted Pyridines
  作者：Sheng Liu、James Sawicki、Tom G. Driver

  DOI：10.1021/ol301606y

  日期：2012.7.20

  A synthetic strategy to access 2,6-disubstituted pyridines from triazolopyridines through a regioselective nickel-catalyzed alkenylation reaction of the C7–H bond is described. The N2 fragment embedded in the resulting C–H functionalized triazolopyridine can be readily excised using acidic or oxidative conditions to unmask the pyridine.

  描述了通过区域选择性镍催化的C7–H键烯基化反应从三唑并吡啶获得2，6-二取代吡啶的合成策略。可以使用酸性或氧化性条件轻易地切除嵌入到C–H官能化的三唑并吡啶中的N 2片段，从而使吡啶不被掩盖。
• Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes
  作者：Xiaoxu Wang、Jing Ke、Yiling Zhu、Arghya Deb、Yijie Xu、X. Peter Zhang

  DOI：10.1021/jacs.1c04655

  日期：2021.7.28

  applicable to α-pyridyl and other α-heteroaryldiazomethanes for asymmetric cyclopropanation of wide-ranging alkenes, including several types of challenging substrates. This new catalytic methodology provides a general access to valuable chiral heteroaryl cyclopropanes in high yields with excellent both diastereoselectivities and enantioselectivities. Combined computational and experimental studies further

  通过Co(II)基金属自由基催化(MRC)，开发了一种高效催化方法，用于烯烃与原位生成的α-杂芳基重氮甲烷的不对称自由基环丙烷化。通过对新合成的D 2 -对称手性酰胺卟啉作为支持配体的类空腔环境进行微调，优化的Co(II)基金属自由基体系广泛适用于α-吡啶基和其他α-杂芳基重氮甲烷，用于不对称环丙烷化范围广泛的烯烃，包括几种类型的具有挑战性的底物。这种新的催化方法提供了以高产率获得有价值的手性杂芳基环丙烷的通用途径，并具有优异的非对映选择性和对映选择性。计算和实验相结合的研究进一步支持了以α-和γ-金属烷基自由基作为关键中间体的Co(II)基烯烃环丙烷化的基本逐步自由基机理。
• I₂-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused 1,2,4-triazoles from N-tosylhydrazones and aromatic N-heterocycles via intermolecular formal 1,3-dipolar cycloaddition
  作者：Surendra Babu Inturi、Biswajit Kalita、A. Jafar Ahamed

  DOI：10.1039/c6ob01926a

  日期：——

  I2-TBHP-catalyzed azomethine imine generation and subsequent regioselective 1,3-dipolar cycloaddition (DC) with aromatic N-heterocycles was developed to afford various 4,3-fused 1,2,4-triazoles in excellent yields. The method is operationally simple and highly efficient with broad functional group tolerance.

  开发了I 2 -TBHP催化的偶氮甲亚胺亚胺和随后的具有芳香族N-杂环的区域选择性1，3-偶极环加成（DC），以优异的产率提供了各种4，3-稠合的1,2,4-三唑。该方法操作简便且高效，具有宽泛的官能团耐受性。
• Cobalt(II)-based Metalloradical Activation of 2-(Diazomethyl)pyridines for Radical Transannulation and Cyclopropanation
  作者：Satyajit Roy、Sandip Kumar Das、Buddhadeb Chattopadhyay

  DOI：10.1002/anie.201711209

  日期：2018.2.19

  A new catalytic method for the denitrogenative transannulation/cyclopropanation of in‐situ‐generated 2‐(diazomethyl)pyridines is described using a cobalt‐catalyzed radical‐activation mechanism. The method takes advantage of the inherent properties of a CoIII‐carbene radical intermediate and is the first report of denitrogenative transannulation/cyclopropanation by a radical‐activation mechanism, which

  介绍了一种利用钴催化的自由基活化机理对原位生成的2-（重氮甲基）吡啶进行脱氮环转移/环丙烷化的新催化方法。该方法利用了Co III-卡宾自由基中间体的固有性质，并且是通过自由基激活机制进行脱氮脱环/环丙烷化的第一篇报道，并得到了各种控制实验的支持。（±）-单morine的总合成时间短，证明了金属-金属法的综合优势。
• Synthesis and Evaluation of Novel Radioligands Based on 3-[5-(Pyridin-2-yl)-2<i>H</i>-tetrazol-2-yl]benzonitrile for Positron Emission Tomography Imaging of Metabotropic Glutamate Receptor Subtype 5
  作者：Yoko Shimoda、Tomoteru Yamasaki、Masayuki Fujinaga、Masanao Ogawa、Yusuke Kurihara、Nobuki Nengaki、Katsushi Kumata、Joji Yui、Akiko Hatori、Lin Xie、Yiding Zhang、Kazunori Kawamura、Ming-Rong Zhang

  DOI：10.1021/acs.jmedchem.6b00209

  日期：2016.4.28

  autoradiography and PET assessments using [11C]10 showed high specific binding in the striatum and hippocampus, two brain regions enriched with mGluR5. Moreover, test–retest PET studies with [11C]10 indicated high reliability to quantify mGluR5 density, such as the intraclass correlation coefficient (0.90) and Pearson r (0.91) in the striatum of rat brain. We demonstrated that [11C]10 is a useful PET ligand for imaging

  我们发现3- [5-（吡啶-2-基）-2 H-四唑-2-基]苄腈类似物作为代谢型谷氨酸受体亚型5（mGluR5）的正电子发射断层扫描（PET）成像剂的候选者。在这些化合物中，3-甲基-5-（5-（吡啶-2-基）-2 H-四唑-2-基）苯甲腈（10）表现出高结合亲和力（K i = 9.4 nM）和适度的亲脂性（cLogD ，2.4）。随后，通过芳基锡烷基前体15与[ 11 ]的C- [ 11 C]甲基化，以25±14％的放射化学收率（n = 11）放射性合成[ 11 C] 10。C]甲基碘。使用[ 11 C] 10进行的体外放射自显影和PET评估显示纹状体和海马体（两个富含mGluR5的大脑区域）具有高特异性结合。此外，以[ 11 C] 10进行的再测试PET研究表明，对mGluR5密度进行定量具有很高的可靠性，例如大鼠脑纹状体中的类内相关系数（0.90）和Pearson r（0.91）。我们证明[