3-(4-nitroanilino)-1,2-dihydro-1-isoquinoline | 500198-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-(4-nitroanilino)-1,2-dihydro-1-isoquinoline
• 英文别名: 3-(4-nitroanilino)isoquinolin-1(2H)-one；3-(4-Nitroanilino)-1(2h)-isoquinolinone；3-(4-nitroanilino)-2H-isoquinolin-1-one
• CAS: 500198-67-4
• 化学式: C₁₅H₁₁N₃O₃
• 分子量: 281.271
• InChiKey: BDPTZRDQXNDTMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-nitroanilino)-1,2-dihydro-1-isoquinoline 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Fused isoquinolines: 3-aryl-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-4′-(1′-alkyl-1′,4′-dihydropyridine)s

  摘要：

  Previously unknown 3-arylamino-1,2-dihydro-1-isoquinolones were obtained by condensation of 2-cyanomethylbenzoic acid with arylamines. Isonicotinoylation of the compounds was shown to proceed at the carbon atom in the 4-position to give 3-arylamino-4-isonicotinoyl-1,2-dihydro-1-isoquinolones which were quaternized with alkylating agents and formed the corresponding pyridinium salts. Deprotonation of the latter induced intramolecular conjugated addition with the pyrrole ring closure and formation of spiro compounds. The structure of the products was confirmed by NMR, IR and UV spectroscopy and by synthesis of the model compound, 3-(4-tolyl)-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.009
• 作为产物：
  描述：

  2-(氰基甲基)苯甲酸 、 4-硝基苯胺 以 氯苯 为溶剂， 反应 5.0h， 以85%的产率得到3-(4-nitroanilino)-1,2-dihydro-1-isoquinoline
  参考文献：
  名称：

  Fused isoquinolines: 3-aryl-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-4′-(1′-alkyl-1′,4′-dihydropyridine)s

  摘要：

  Previously unknown 3-arylamino-1,2-dihydro-1-isoquinolones were obtained by condensation of 2-cyanomethylbenzoic acid with arylamines. Isonicotinoylation of the compounds was shown to proceed at the carbon atom in the 4-position to give 3-arylamino-4-isonicotinoyl-1,2-dihydro-1-isoquinolones which were quaternized with alkylating agents and formed the corresponding pyridinium salts. Deprotonation of the latter induced intramolecular conjugated addition with the pyrrole ring closure and formation of spiro compounds. The structure of the products was confirmed by NMR, IR and UV spectroscopy and by synthesis of the model compound, 3-(4-tolyl)-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.009

文献信息

• Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones
  作者：L. M. Potikha、R. M. Gutsul、A. S. Plaskon、V. A. Kovtunenko、A. A. Tolmachev

  DOI：10.1007/s10593-011-0763-7

  日期：2011.6

  acid leads to the formation of derivatives of dibenzo[b,f][1, 8]naphthyridin-5(6H)- one and benzo[f]isoquino[3,4-b][1, 8]naphthyridine-5,9(6H,7H)-dione. The reaction for R = Het in the presence of Me3SiCl gives derivatives of 5H-pyrido[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one, benzo[f]isoquinoline[3,4-b][1,8]naphthyridine-5,9[6H,7H]-dione, and derivatives of new heterocyclic systems, 5H-pyrazino[1'

  在Me3SiCl存在下或在乙酸中，3-NHR-异喹啉-1（2H）-一（R = Ar）与芳族醛的反应导致二苯并[b，f] [1，8]衍生物的形成萘啶-5（6H）-1和苯并[f]异喹啉[3,4-b] [1，8]萘啶-5,9（6H，7H）-二酮。在Me3SiCl存在下，R = Het的反应给出5H-吡啶基[1'，2'：1,2]嘧啶基[4,5-c]异喹啉-5-酮，苯并[f]异喹啉[3， 4-b] [1,8]萘啶-5,9 [6H，7H]-二酮和新杂环系统的衍生物5H-pyrazino [1'，2'：1,2] pyrimido [4,5-c ]异喹啉-5-酮，5H- [1,3]噻唑洛[3'，2'：1,2]嘧啶基-[4,5-c]异喹啉-5-酮，5-H-苯并[f]吡唑啉[3，4-b] [1，8]萘啶-5-酮和异喹啉[3，4-b]-[1，5]萘啶-5（6H）-酮。
• Fused isoquinolines: 3-aryl-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-4′-(1′-alkyl-1′,4′-dihydropyridine)s
  作者：Tat'yana T Kucherenko、Roman Gutsul、Vladimir M Kisel、Vladimir A Kovtunenko

  DOI：10.1016/j.tet.2003.10.009

  日期：2004.1

  Previously unknown 3-arylamino-1,2-dihydro-1-isoquinolones were obtained by condensation of 2-cyanomethylbenzoic acid with arylamines. Isonicotinoylation of the compounds was shown to proceed at the carbon atom in the 4-position to give 3-arylamino-4-isonicotinoyl-1,2-dihydro-1-isoquinolones which were quaternized with alkylating agents and formed the corresponding pyridinium salts. Deprotonation of the latter induced intramolecular conjugated addition with the pyrrole ring closure and formation of spiro compounds. The structure of the products was confirmed by NMR, IR and UV spectroscopy and by synthesis of the model compound, 3-(4-tolyl)-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione. (C) 2003 Elsevier Ltd. All rights reserved.