4-(ferrocenylideneamino)-5-ferrocenyl-2H-1,2,4-triazole-3(4H)-thione | 1197241-95-4

• 英文名称: 4-(ferrocenylideneamino)-5-ferrocenyl-2H-1,2,4-triazole-3(4H)-thione
• CAS: 1197241-95-4
• 化学式: C₂₃H₂₀Fe₂N₄S
• 分子量: 496.199
• InChiKey: NXCMLEYDUYRWKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  4-(ferrocenylideneamino)-5-ferrocenyl-2H-1,2,4-triazole-3(4H)-thione 、 碘甲烷 在 Na 、 CH₃OH 作用下， 以 甲醇 为溶剂， 以82%的产率得到3-methylthio-4-(ferrocenylmethylideneamino)-5-ferrocenyl-4H-1,2,4-triazol
  参考文献：
  名称：

  Synthesis, ring transformations, IR-, NMR and DFT study of heterocycles with two ferrocenyl units

  摘要：

  Cyclization of 1,5-bis(ferrocenylmethylidene) thiocarbonohydrazide with DMAD afforded diastereomeric dimethyl-thiazole-4,5-dicarboxylates. The cis-isomer undergoes ring opening and recyclization to a thiazolone derivative. A further thiazolone was obtained from this precursor with ethyl chloroacetate employing a bifunctional organocatalyst. Due to its propensity to dehydrogenation evidenced by DFT calculations, the studied thiocarbonohydrazide underwent oxidative cyclizations under different conditions to yield a 1,3,4-thiadiazole and a 1,2,4-triazole derivative, respectively. Thermal isomerisation of 1,3,4-thiadiazole into 1,2,4-triazole was also observed. The DMAD-mediated cyclizations of the S-metylated thiocarbonohydrazide and the 1,5-bis(ferrocenylmethylideneamino)guanidine gave 1,2,4-triazole derivatives and a 4-pyrimidone, respectively. The structure of the new compounds was established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements. The solid state structure of a triazole was revealed by single crystal X-ray analysis. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.07.038
• 作为产物：
  描述：

  2-ferrocenyl-1-(5-ferrocenyl-1,3,4-thiadiazol-2-yl)hydrazine 以 xylene 为溶剂， 以50%的产率得到4-(ferrocenylideneamino)-5-ferrocenyl-2H-1,2,4-triazole-3(4H)-thione
  参考文献：
  名称：

  Synthesis, ring transformations, IR-, NMR and DFT study of heterocycles with two ferrocenyl units

  摘要：

  Cyclization of 1,5-bis(ferrocenylmethylidene) thiocarbonohydrazide with DMAD afforded diastereomeric dimethyl-thiazole-4,5-dicarboxylates. The cis-isomer undergoes ring opening and recyclization to a thiazolone derivative. A further thiazolone was obtained from this precursor with ethyl chloroacetate employing a bifunctional organocatalyst. Due to its propensity to dehydrogenation evidenced by DFT calculations, the studied thiocarbonohydrazide underwent oxidative cyclizations under different conditions to yield a 1,3,4-thiadiazole and a 1,2,4-triazole derivative, respectively. Thermal isomerisation of 1,3,4-thiadiazole into 1,2,4-triazole was also observed. The DMAD-mediated cyclizations of the S-metylated thiocarbonohydrazide and the 1,5-bis(ferrocenylmethylideneamino)guanidine gave 1,2,4-triazole derivatives and a 4-pyrimidone, respectively. The structure of the new compounds was established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements. The solid state structure of a triazole was revealed by single crystal X-ray analysis. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.07.038