5,6-dihydro-4H-indolo<3,2,1-ij><1,6>naphthyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,6-dihydro-4H-indolo<3,2,1-ij><1,6>naphthyridine
• 英文别名: 5,6-dihydro-4H-indolo[3,2,1-ij]-1,6-naphthyridine；5,6-dihydro-4H-indolo[3,2,1-ij][1,6]naphthyridine；isocanthine；1,7-Diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16),10,12,14-hexaene
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: JXRKCALIKAXETO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-碘-1-戊炔 在 palladium diacetate 、 三甲基氯硅烷 、 盐酸羟胺 、 水 、 potassium acetate 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 sodium iodide 、 三氯氧磷 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 42.25h， 生成 5,6-dihydro-4H-indolo<3,2,1-ij><1,6>naphthyridine
  参考文献：
  名称：

  1—Azatriene cyclisation as a route to annelated pyrido[4,3- b ]indoles

  摘要：

  Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the alpha-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two atoms. cyclised in boiling toluene. The cyclisation led to the formation of the pyrido-indoles 17 and 18, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00117-8

文献信息

• Intramolecular Diels–Alder reaction for the synthesis of tetracyclic carbazoles and isocanthines
  作者：Prajakta N. Naik、Ayesha Khan、Radhika S. Kusurkar

  DOI：10.1016/j.tet.2013.10.054

  日期：2013.12

  One pot intramolecular Diels–Alder reaction has been efficiently used as a new route for the synthesis of four tetracyclic carbazoles and four isocanthine analogues where a dialdehyde is utilised as a common intermediate for both the scaffolds. Biological activity was evaluated for some molecules, which demonstrated moderate activity against HeLa cervical cancer cell lines.

  一锅内分子内Diels-Alder反应已被有效地用作合成四个四环咔唑和四个异鸟氨酸类似物的新途径，其中二醛被用作两个支架的共同中间体。生物活性评价了一些分子，其表现出中等活性对宫颈癌HeLa细胞系。
• Intramolecular Hetero Diels–Alder Routes to γ-Carboline Alkaloids
  作者：Scott A Snyder、David A Vosburg、Matthew G Jarvis、J.Hodge Markgraf

  DOI：10.1016/s0040-4020(00)00468-3

  日期：2000.7

  Concise and efficient routes to the carboline alkaloids isocanthine (3), isocanthin-6-one (4), 1-methylisocanthine (5), and 1-methylisocanthin-6-one (6) are reported. In each case, the key synthetic step was an intramolecular hetero Diels–Alder reaction of a 1-aza-1,3-diene with an acetylenic dienophile.

  简明和高效的路由到咔啉生物碱isocanthine（3），isocanthin -6-酮（4），1- methylisocanthine（5），和1- methylisocanthin -6-酮（6被报告）。在每种情况下，关键的合成步骤是1-氮杂-1,3-二烯与炔属二烯亲和物的分子内杂狄尔斯-阿尔德反应。
• Synthesis of Annulated <i>γ</i>-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0343228

  日期：2003.6.1

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.
• Germain, Andrew L.; Gilchrist, Thomas L.; Kemmitt, Paul D., Heterocycles, 1994, vol. 37, # 2, p. 697 - 700
  作者：Germain, Andrew L.、Gilchrist, Thomas L.、Kemmitt, Paul D.

  DOI：——

  日期：——
• 1—Azatriene cyclisation as a route to annelated pyrido[4,3- b ]indoles
  作者：Thomas L. Gilchrist、Paul D. Kemmitt、Andrew L. Germain

  DOI：10.1016/s0040-4020(97)00117-8

  日期：1997.3

  Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the alpha-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two atoms. cyclised in boiling toluene. The cyclisation led to the formation of the pyrido-indoles 17 and 18, respectively. (C) 1997 Elsevier Science Ltd.