1,2-dihydro-5-nitroso-6-(phenylamino)-2-thioxopyrimidin-4(3H)-one | 407627-38-7

• 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: 1,2-dihydro-5-nitroso-6-(phenylamino)-2-thioxopyrimidin-4(3H)-one
• CAS: 407627-38-7
• 化学式: C₁₀H₈N₄O₂S
• 分子量: 248.265
• InChiKey: JEDWOVAJSUYPCT-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.11
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (phenylhydrazono)chloroacetate 、 1,2-dihydro-5-nitroso-6-(phenylamino)-2-thioxopyrimidin-4(3H)-one 以 氯仿 为溶剂， 生成 ethyl (1-phenyl-6-nitroso-7-phenylamino-5-oxo-1,2,4-triazolo[4,3-a]pyrimidin-3-yl)carboxylate
  参考文献：
  名称：

  Novel synthesis of 1,2,4-triazolo[4,3- a ]pyrimidin-5-one derivatives

  摘要：

  1,2-Dihydro-2-thioxopyrimidin-4(3H)ones 6 react with C-ethoxycarbonyl-N-arylhydrazonoyl chlorides 1 to give 1,2,4-triazolo[4,3-a] pyrimidines 11 in good yield. The latter products 11 react with benzenediazonium chloride, nitrous acid, acetyl chloride and chloroacetyl chloride to give the corresponding substitution products 16-18. The structures of the newly synthesized compounds are established on the basis of chemical and spectroscopic evidence. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01026-2
• 作为产物：
  描述：

  6-苯胺基-2-硫代尿嘧啶 在 溶剂黄146 、 sodium nitrite 作用下， 生成 1,2-dihydro-5-nitroso-6-(phenylamino)-2-thioxopyrimidin-4(3H)-one
  参考文献：
  名称：

  Novel synthesis of 1,2,4-triazolo[4,3- a ]pyrimidin-5-one derivatives

  摘要：

  1,2-Dihydro-2-thioxopyrimidin-4(3H)ones 6 react with C-ethoxycarbonyl-N-arylhydrazonoyl chlorides 1 to give 1,2,4-triazolo[4,3-a] pyrimidines 11 in good yield. The latter products 11 react with benzenediazonium chloride, nitrous acid, acetyl chloride and chloroacetyl chloride to give the corresponding substitution products 16-18. The structures of the newly synthesized compounds are established on the basis of chemical and spectroscopic evidence. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01026-2

文献信息

• Synthesis of 1,2,4-Triazolo[4,3-a]pyrimidine Derivatives by Cyclocondensation of a 2-Thioxopyrimidin-4(3H)-one with Hydrazonoyl Halides
  作者：Nehal M. Elwan、Enas M. Awad、Hamdi M. Hassaneen、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/hlca.200390073

  日期：2003.3

  The reaction of 1,2-dihydro-6-(phenylamino)-2-thioxopyrimidin-4(3H)one (16) with N-arylhydrazonoyl halides 15 in CHCl3 in the presence of Et3N under reflux afforded the corresponding 1,2,4-triazolo[4,3-a]pyrimidin-5-ones of type 20 in good yields (Scheme 3). The structure of one of the derivatives, 20d, has been established by X-ray crystallography. Conceivable reaction mechanisms are discussed in

  的1,2-二氢-6-（苯基氨基）反应-2- thioxopyrimidin-4（3 ħ）一（16）与Ñ -arylhydrazonoyl卤化物15在CHCl 3中的的Et存在下3氮气氛下回流，得到相应的1-类型20的，2，4-三唑并[4，3- a ]嘧啶-5-酮具有良好的收率（方案3）。一种衍生物20d的结构已经通过X射线晶体学确定。流程3和4中讨论了可能的反应机理。类型20的产物容易经历与亲电子试剂如重氮苯酰氯，氯乙酰氯，和纳米反应2的AcOH，得到6-苯基偶氮，6-氯乙酰基，和6-亚硝基衍生物21,23和25，分别为（方案5）。