(Z)-2-Cyano-3-{2-[(E)-phenyliminomethyl]-phenylamino}-but-2-enedioic acid dimethyl ester | 142188-39-4

• 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: (Z)-2-Cyano-3-{2-[(E)-phenyliminomethyl]-phenylamino}-but-2-enedioic acid dimethyl ester
• CAS: 142188-39-4
• 化学式: C₂₀H₁₇N₃O₄
• 分子量: 363.373
• InChiKey: CAAHEEITPDMEJY-LTGBVJNTSA-N

物化性质

• 沸点：
  530.9±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  在 potassium cyanide 作用下， 以 水 为溶剂， 以60%的产率得到(Z)-2-Cyano-3-{2-[(E)-phenyliminomethyl]-phenylamino}-but-2-enedioic acid dimethyl ester
  参考文献：
  名称：

  Reaction of N-vinylpyrazolium and N-vinylindazolium salts with cyanide ion: formation of 1,2-dihydropyrimidines, 3,4-dihydroquinazolines, and quinolines

  摘要：

  The reaction of 1-aryl-2-vinylpyrazolium tetrafluoroborates with potassium cyanide affords 2-hydroxy-1,2-dihydropyrimidines 3, which exist as open-chain tautomers 4, both in the solid state and in solution. The X-ray structure of the p-chlorophenyl derivative 4b has been determined (ClC14N2O3H15, P2(1)/c, a = 11.433 (3) angstrom, b = 16.086 (4) angstrom, c = 7.813 (4) angstrom, beta = 94.22 (5)-degrees, V = 1433.0 (9), Z = 4, R = 0.06 for 1334 observed reflections). Protonation of these vinylogous amidines 4 results in their cyclization and dehydration to pyrimidinium salts 6. In the case of 1-vinyl-2-methylindazolium tetrafluoroborate 8, the reaction with cyanide ion leads to a mixture of 3,4-dihydroquinazoline 12 and 2-(methoxycarbonyl)-3-cyanoquinoline (13). The mechanism proposed for this rearrangement is supported by the isolation of the open-chain intermediate in the case of 1-vinyl-2-phenylindazolium salt.

  DOI：

  10.1021/jo00041a018