2-pyridylsulfonyl azide | 152278-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-pyridylsulfonyl azide
• 英文别名: 2-pyridinesulfonyl azide；(NE)-N-diazopyridine-2-sulfonamide
• CAS: 152278-13-2
• 化学式: C₅H₄N₄O₂S
• 分子量: 184.178
• InChiKey: MGORLNBYCOFNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-pyridylsulfonyl azide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 25.0 ℃ 、241.32 kPa 条件下， 反应 12.0h， 生成 1-methylpiperidylidene-2-(2-pyridyl)sulfonamide
  参考文献：
  名称：

  Synthesis and antinociceptive activity of 1-methylpiperidylidene-2-(pyridyl)sulfonamides and related dihydropyridyl analogs

  摘要：

  The regiospecific 1,3-dipolar cycloaddition reaction of 1-methyl-1,2-dihydropyridine 2 with 2-, 3- or 4-pyridylsulfonyl azide 3a-c yielded the respective 1-methyl-1,2,3,6-tetrahydropyridylidene-2-(2-, 3- or 4-pyridyl)sulfonamides 5a-c. Hydrogenation of 5a-c afforded the corresponding 1-methylpiperldylidene-2-(pyridyl)sulfonamides 1a-c. Compounds lb and 1c were elaborated to 1',6'- 6a-d and 1',4'- 7a-c, and 1',2'-dihydropyridines 8a-e, respectively by quaternization with phenyl chloroformate followed by in situ reaction with methyl-, n-butyl-, t-butyl- or phenylmagnesium chloride, or sodium borohydride. Antinociceptive activity was determined using the rat sodium chloride-induced writhing assay. The point of attachment of the pyridyl ring was a determinant of activity where the relative activity order was 2-pyridyl la greater-than-or-equal-to 4-pyridyl 1c > 3-pyridyl 1b (ED50) values of 6.2, 9.0 and 6.6 mg/kg sc, respectively), relative to the reference drug meperidine (EC50 = 0.6 mg/kg sc). The pyridyl compounds lb,1c were more potent than their dihydropyridyl derivatives 6a-d, 8a-e. The most active dihydropyridyl derivative, 1-methylpiperidylidene-2-(1',2'-dihydro-2'-t-butyl-1'-phenoxycarbonyl-4'-pyridyl)sulfonamide 8c was more active at 25 mg/kg sc (68% inhibition of writhing) than aspirin at 50 mg/kg sc (58% inhibition of writhing). In the dihydropyridyl series of compounds 6a-d, 8a-e, a t-Bu substituent at the alpha-position of the 1',6'- or 1',2'-dihydropyridyl ring provided superior antinociceptive activity relative to that of a H, Me. n-Bu or Ph substituent.

  DOI：

  10.1016/0223-5234(93)90012-4
• 作为产物：
  描述：

  吡啶-2-磺酰氯 在 sodium azide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以66%的产率得到2-pyridylsulfonyl azide
  参考文献：
  名称：

  Synthesis and antinociceptive activity of 1-methylpiperidylidene-2-(pyridyl)sulfonamides and related dihydropyridyl analogs

  摘要：

  The regiospecific 1,3-dipolar cycloaddition reaction of 1-methyl-1,2-dihydropyridine 2 with 2-, 3- or 4-pyridylsulfonyl azide 3a-c yielded the respective 1-methyl-1,2,3,6-tetrahydropyridylidene-2-(2-, 3- or 4-pyridyl)sulfonamides 5a-c. Hydrogenation of 5a-c afforded the corresponding 1-methylpiperldylidene-2-(pyridyl)sulfonamides 1a-c. Compounds lb and 1c were elaborated to 1',6'- 6a-d and 1',4'- 7a-c, and 1',2'-dihydropyridines 8a-e, respectively by quaternization with phenyl chloroformate followed by in situ reaction with methyl-, n-butyl-, t-butyl- or phenylmagnesium chloride, or sodium borohydride. Antinociceptive activity was determined using the rat sodium chloride-induced writhing assay. The point of attachment of the pyridyl ring was a determinant of activity where the relative activity order was 2-pyridyl la greater-than-or-equal-to 4-pyridyl 1c > 3-pyridyl 1b (ED50) values of 6.2, 9.0 and 6.6 mg/kg sc, respectively), relative to the reference drug meperidine (EC50 = 0.6 mg/kg sc). The pyridyl compounds lb,1c were more potent than their dihydropyridyl derivatives 6a-d, 8a-e. The most active dihydropyridyl derivative, 1-methylpiperidylidene-2-(1',2'-dihydro-2'-t-butyl-1'-phenoxycarbonyl-4'-pyridyl)sulfonamide 8c was more active at 25 mg/kg sc (68% inhibition of writhing) than aspirin at 50 mg/kg sc (58% inhibition of writhing). In the dihydropyridyl series of compounds 6a-d, 8a-e, a t-Bu substituent at the alpha-position of the 1',6'- or 1',2'-dihydropyridyl ring provided superior antinociceptive activity relative to that of a H, Me. n-Bu or Ph substituent.

  DOI：

  10.1016/0223-5234(93)90012-4

文献信息

• Copper−Nitrenoid Formation and Transfer in Catalytic Olefin Aziridination Utilizing Chelating 2-Pyridylsulfonyl Moieties
  作者：Hoon Han、Seong Byeong Park、Sang Kyu Kim、Sukbok Chang

  DOI：10.1021/jo800134j

  日期：2008.4.1

  developed an efficient protocol for copper-catalyzed olefin aziridination using 5-methyl-2-pyridinesulfonamide or 2-pyridinesulfonyl azide as the nitrenoid source. The presence of a 2-pyridyl group significantly facilitates aziridination, suggesting that the reaction is driven by the favorable formation of a pyridyl-coordinated nitrenoid intermediate. Using this chelation-assisted strategy, synthetically

  我们已经开发出一种有效的方案，用于使用5-甲基-2-吡啶磺酰胺或2-吡啶磺酰基叠氮化物作为类固醇源的铜催化烯烃叠氮化。2-吡啶基的存在显着促进了叠氮基化，表明该反应是由吡啶基配位的亚硝基化合物中间体的有利形成驱动的。使用这种螯合辅助策略，即使在没有外部配体的情况下，使用一系列芳基烯烃也可以获得合成可接受的氮丙啶收率。重要的是，不需要大量过量的烯烃。X射线晶体学，ESI-MS，哈米特图分析，动力学研究和计算工作都强烈支持观察到的叠氮化是由内部配位驱动的。
• Synthesis of Sulfonyl Azides
  作者：Alan Katritzky、Khalid Widyan、Kapil Gyanda

  DOI：10.1055/s-2008-1072568

  日期：2008.4

  1-(Alkylsulfonyl)- and 1-(arylsulfonyl)benzotriazoles react with sodium azide in acetonitrile to give the corresponding alkanesulfonyl and arenesulfonyl azides.

  1-（烷基磺酰基）和1-（芳基磺酰基）苯并三氮唑与氰化钠在丙酮腈中反应，生成相应的烷基磺酰基和芳基磺酰基叠氮化合物。
• A copper-catalyzed multicomponent reaction for the synthesis of thioamide skeletons
  作者：Mehdi Khalaj

  DOI：10.1007/s00706-019-02525-0

  日期：2020.1

  situ generated sulfide has been reacted with sulfonylketimine derived from the reaction of alkynes and sulfonyl azides by the action of copper salts to form a wide range of thioamide derivatives. Various terminal alkynes including aromatic, heteroaromatic, and aliphatic alkynes have been well tolerated and the reaction also shows good generality along with azides. Graphic abstract

  摘要在该报告中，通过铜盐的作用，将原位生成的硫化物与衍生自炔烃和磺酰叠氮化物反应的磺酰酮亚胺反应，形成了多种硫酰胺衍生物。包括芳族，杂芳族和脂族炔在内的各种末端炔均具有良好的耐受性，该反应与叠氮化物也显示出良好的通用性。 图形摘要
• Catalytic One-Pot Synthesis of Cyclic Amidines by Virtue of Tandem Reactions Involving Intramolecular Hydroamination under Mild Conditions
  作者：Sukbok Chang、Minjae Lee、Doo Young Jung、Eun Jeong Yoo、Seung Hwan Cho、Sun Kyu Han

  DOI：10.1021/ja064788i

  日期：2006.9.1

  A new synthetic methodology for the generation of cyclic amidines has been developed by the reaction of 1,n-aminoalkynes with electron-deficient azides using a ruthenium catalyst at ambient temperature. The reaction proceeds most likely via a tandem sequence of intramolecular hydroamination of aminoalkynes, cycloaddition of azides with the resulting enamines, and rearrangement of triazoline intermediates

  通过在环境温度下使用钌催化剂使 1,n-氨基炔烃与缺电子叠氮化物反应，开发了一种用于生成环脒的新合成方法。该反应最有可能通过氨基炔烃的分子内加氢胺化、叠氮化物与所得烯胺的环加成以及三唑啉中间体的重排的串联顺序进行。作为原理证明，它证明了平衡级联序列可以由不可逆步骤有利地驱动，从而使简便的一锅合成路线能够在前所未有的温和条件下提供分子复杂性，而无需依赖传统的线性方法。
• Highly Efficient One-Pot Synthesis of <i>N</i>-Sulfonylamidines by Cu-Catalyzed Three-Component Coupling of Sulfonyl Azide, Alkyne, and Amine
  作者：Imhyuck Bae、Hoon Han、Sukbok Chang

  DOI：10.1021/ja0432968

  日期：2005.2.1

  and catalytic multicomponent reaction for the synthesis of N-sulfonylamidines has been developed. This reaction has an extremely wide scope with regard to all three coupling components of alkyne, sulfonyl azide, and amine. Two plausible mechanistic pathways involving ketenimine or triazole intermediate are tentatively presented for the copper-catalyzed three-component coupling reactions.

  已开发出一种用于合成 N-磺酰脒的高效、温和、实用且具有催化作用的多组分反应。该反应对于炔、磺酰叠氮化物和胺的所有三种偶联组分具有极其广泛的范围。对于铜催化的三组分偶联反应，初步提出了涉及烯酮亚胺或三唑中间体的两种可能的机制途径。