<1,2,5>oxadiazolo<3,4-b>pyridine 1-oxide | 27808-53-3

• 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: <1,2,5>oxadiazolo<3,4-b>pyridine 1-oxide
• 英文别名: pyrido<2,3-c>furoxane；Pyrido<2,3-c>furoxan；[1,2,5]oxadiazolo[3,4-b]pyridine 3-oxide；7-Azabenzofuroxan；3-Oxo-3lambda~5~-[1,2,5]oxadiazolo[3,4-b]pyridine；3-oxido-[1,2,5]oxadiazolo[3,4-b]pyridin-3-ium
• CAS: 27808-53-3
• 化学式: C₅H₃N₃O₂
• mdl: MFCD09836156
• 分子量: 137.098
• InChiKey: IVVIALUNNKYDQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  52 °C
• 沸点：
  269.1±32.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  <1,2,5>oxadiazolo<3,4-b>pyridine 1-oxide 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2-Nitro-6-morpholinopyridine
  参考文献：
  名称：

  吡咯并[2,3-c]呋喃喃作为2-硝基-3-叠氮基吡啶与胺反应的可能中间体

  摘要：

  DOI：

  10.1007/bf00505694
• 作为产物：
  描述：

  2-nitro-3-azidopyridine 以 萘烷 为溶剂， 生成 <1,2,5>oxadiazolo<3,4-b>pyridine 1-oxide
  参考文献：
  名称：

  Dyall, Leonard K.; Wah, Wong Ming, Australian Journal of Chemistry, 1985, vol. 38, # 7, p. 1045 - 1059

  摘要：

  DOI：

文献信息

• Oxidative Cyclizations. VIII. Mechanisms of Oxidation of ortho-Substituted Benzenamines and Improved Cyclizations by Bis(acetato-O)Phenyliodine
  作者：LK Dyall、JJ Harvey、TB Jarman

  DOI：10.1071/ch9920371

  日期：——

  Published reports describe the oxidative cyclization of suitable ortho-substituted arenamines to form such products as 2,1-benzisoxazoles, benzofurazan 1-oxides and benzotriazoles, by using bis(acetato-O)phenyliodine at room temperature. However, the reactions are often inconveniently slow. We now report attempts to achieve short reaction times with more powerful iodine(III) oxidants. These often failed to give cyclic products, but the results enable us to argue that the reaction competing with cyclization involves the arenaminyl, cation ArN+H. When such cations are predicted to be relatively unstable, the parent arenamine can be rapidly cyclized in high yield by oxidation with bis(acetato-O)phenyliodine in boiling benzene.

  已发表的报告介绍了在室温下使用双（乙酰氧基）苯基碘对合适的正交取代的芳胺进行氧化环化，生成 2,1-苯并异噁唑、苯并呋喃 1-氧化物和苯并三唑等产物。然而，这些反应通常速度很慢，很不方便。现在，我们报告了使用更强的碘(III)氧化剂来缩短反应时间的尝试。这些尝试往往不能得到环状产物，但结果使我们能够论证，与环化反应竞争的反应涉及芳酰胺基阳离子 ArN+H。当预测这种阳离子相对不稳定时，在沸腾的苯中用双（乙酰-O）苯基碘进行氧化，母体芳酰胺就能迅速环化，而且产量很高。
• Synthesis of polynuclear heterocycles. Part II. Cyclisations of 2- and 4-substituted 3-amino- and 3-nitro-pyridines
  作者：J. J. Eatough、L. S. Fuller、R. H. Good、R. K. Smalley

  DOI：10.1039/j39700001874

  日期：——

  Treatment of 2- and 4-phenoxy-3-nitropyridine with triethyl phosphite failed to yield the expected pyridobenz-oxazines; 2- and 4-phenylthio-3-nitropyridine, however, cyclised to give 5H-pyrido [2,3-b][1,4] benzothiazine and 5H-pyrido[3,4-b][1,4]benzothiazine respectively, albeit in poor yield. Similar results were obtained by thermolytic decomposition of the corresponding 2- and 4-substituted 3-azido-pyridines

  用亚磷酸三乙酯处理2-和4-苯氧基-3-硝基吡啶不能得到预期的吡啶并恶唑。然而，将2-和4-苯硫基-3-硝基吡啶环化，得到5 H-吡啶[2,3- b ] [1,4]苯并噻嗪和5 H-吡啶[3,4- b ] [1,4]苯并噻嗪虽然收率差。通过相应的2-和4-取代的3-叠氮基吡啶的热解分解获得相似的结果。已经合成了9-羟基吡啶并[2,3- b ] 1,4,5-苯并二氮杂卓。
• Nucleophilic substitution in o-nitro azides of the pyridine series
  作者：S. K. Kotovskaya、G. A. Mokrushina、I. Ya. Postovskii

  DOI：10.1007/bf00513266

  日期：1983.3
• Furoxan rearrangement of some pyridofuroxan derivatives studied by1H,13C,14N,15N and17O NMR spectroscopy
  作者：P. Cmoch、B. Kamie?ski、K. Kamie?ska-Trela、L. Stefaniak、G. A. Webb

  DOI：10.1002/1099-1395(200008)13:8<480::aid-poc268>3.0.co;2-z

  日期：2000.8

  Pyridofuroxan ([1,2,5]oxodiazolo[3,4-b]pyridine 1-oxide) undergoes isomerization between the N1-oxide and N3-oxide forms which can be observed by the H-1, C-13 and N-15 NMR spectroscopy but not by N-14 and O-17 NMR at ambient and low temperatures. The rearrangement becomes slower at low temperatures and at 233 K H-1 NMR signals for the two structures become observable. H-1, C-13 and N-15 chemical shifts and H-1-H-1, C-13-H-1 and C-13-C-13 coupling constants are used to characterize both forms in the equilibrium mixture. From the H-1 NMR integrals at 233 K equilibrium constants are calculated. Protonation studies using trifluoroacetic acid as a solvent showed the favoured site of protonation to be the pyridine N4 nitrogen atom. DFT shielding calculations are reported for the C-13, N-15 and O-17 nuclei which support the assignments given. From the point of view of structural changes, (1)J(CC) data for 8-nitrotetrazolo[1,5-a]pyridine and o-nitroaminopyridine as precursors of the pyridofuroxans are given for comparison purposes. X-ray diffraction data on 5-methoxypyridofuroxan support the structural results obtained from the NMR investigations. Copyright (C) 2000 John Wiley & Sons, Ltd.
• KOTOVSKAYA S. K.; MOKRUSHINA G. A.; POSTOVSKIJ I. YA.; POLYAKOVA M. V., XIMIYA GETEROTSIKL. SOEDIN., 1981, NO 5, 654-657
  作者：KOTOVSKAYA S. K.、 MOKRUSHINA G. A.、 POSTOVSKIJ I. YA.、 POLYAKOVA M. V.

  DOI：——

  日期：——