methyl (2-(ferrocenylmethylidenehydrazono)-3-(ferrocenylmethylideneamino)-4-oxothiazol-idin-5-ylidene)acetate | 1197241-76-1

• 英文名称: methyl (2-(ferrocenylmethylidenehydrazono)-3-(ferrocenylmethylideneamino)-4-oxothiazol-idin-5-ylidene)acetate
• CAS: 1197241-76-1
• 化学式: C₂₈H₂₄Fe₂N₄O₃S
• 分子量: 608.284
• InChiKey: HXPZNBROHFPJHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• 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

• 作为产物：
  描述：

  (4R',5S')-dimethyl-2-(ferrocenylmethylidenehydrazono)-3-(ferrocenylmethylideneamino)-thiazolidine-4,5-dicarboxylate 以 乙腈 为溶剂， 以91%的产率得到methyl (2-(ferrocenylmethylidenehydrazono)-3-(ferrocenylmethylideneamino)-4-oxothiazol-idin-5-ylidene)acetate
  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