Pyrazine-2,3-dicarbothioic acid di-S-pyridin-2-yl ester | 187282-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Pyrazine-2,3-dicarbothioic acid di-S-pyridin-2-yl ester
• 英文别名: 2-S,3-S-dipyridin-2-yl pyrazine-2,3-dicarbothioate
• CAS: 187282-68-4
• 化学式: C₁₆H₁₀N₄O₂S₂
• 分子量: 354.413
• InChiKey: FNAKJFCJKOMOID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-溴噻吩 、 Pyrazine-2,3-dicarbothioic acid di-S-pyridin-2-yl ester 在 magnesium 作用下， 生成 7,7-Di-thiophen-2-yl-7H-furo[3,4-b]pyrazin-5-one
  参考文献：
  名称：

  Grignard Reactions on Ortho Dicarboxylic Arene Derivatives. Synthesis of 1,3-Dithienylisothianaphthene Compounds

  摘要：

  1,3-Dithienylisothianaphthene (10a) is obtained through ring closure of 1,2-dithienoylbenzene (7a). The synthesis of 7a has been accomplished based on a Grignard reaction by adding 2-thiophene-magnesium bromide to 1,2-di(S-(2-pyridinyl)) benzenedithioate (6b) to obtain 7a in a yield of 95%. The use of 6b avoids the formation of the corresponding 3,3-dithienyl-3H-isobenzofuran-1(3H)-one (dithienylphthalide, 8). The same procedure is applied to obtain 1,3-dithienyl-4,5,6,7-tetradeuterioisothianaphthene (10b) and 1,3-dithienyl-4,5,6,7-tetrafluoroisothianaphthene (10c). The synthesis of the 2,3-dithienoylpyridine (12a), 3,4-dithienoylpyridine (12b), and 2,3-dithienoylpyrazine (12c) however fails. The presence of nitrogen in the central ring system influences the result of the Grignard reaction. Possibly the free electron pair of the nitrogen interferes with the formation of a stable six-membered ring intermediate which is essential for the diketone formation.

  DOI：

  10.1021/jo9604402
• 作为产物：
  描述：

  2,3-吡嗪二羧酸 在 TEA 、 五氯化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 Pyrazine-2,3-dicarbothioic acid di-S-pyridin-2-yl ester
  参考文献：
  名称：

  Grignard Reactions on Ortho Dicarboxylic Arene Derivatives. Synthesis of 1,3-Dithienylisothianaphthene Compounds

  摘要：

  1,3-Dithienylisothianaphthene (10a) is obtained through ring closure of 1,2-dithienoylbenzene (7a). The synthesis of 7a has been accomplished based on a Grignard reaction by adding 2-thiophene-magnesium bromide to 1,2-di(S-(2-pyridinyl)) benzenedithioate (6b) to obtain 7a in a yield of 95%. The use of 6b avoids the formation of the corresponding 3,3-dithienyl-3H-isobenzofuran-1(3H)-one (dithienylphthalide, 8). The same procedure is applied to obtain 1,3-dithienyl-4,5,6,7-tetradeuterioisothianaphthene (10b) and 1,3-dithienyl-4,5,6,7-tetrafluoroisothianaphthene (10c). The synthesis of the 2,3-dithienoylpyridine (12a), 3,4-dithienoylpyridine (12b), and 2,3-dithienoylpyrazine (12c) however fails. The presence of nitrogen in the central ring system influences the result of the Grignard reaction. Possibly the free electron pair of the nitrogen interferes with the formation of a stable six-membered ring intermediate which is essential for the diketone formation.

  DOI：

  10.1021/jo9604402

文献信息

• Grignard Reactions on <i>Ortho</i> Dicarboxylic Arene Derivatives. Synthesis of 1,3-Dithienylisothianaphthene Compounds
  作者：Rafaël H. L. Kiebooms、Peter J. A. Adriaensens、Dirk J. M. Vanderzande、Jan M. J. V. Gelan

  DOI：10.1021/jo9604402

  日期：1997.3.1

  1,3-Dithienylisothianaphthene (10a) is obtained through ring closure of 1,2-dithienoylbenzene (7a). The synthesis of 7a has been accomplished based on a Grignard reaction by adding 2-thiophene-magnesium bromide to 1,2-di(S-(2-pyridinyl)) benzenedithioate (6b) to obtain 7a in a yield of 95%. The use of 6b avoids the formation of the corresponding 3,3-dithienyl-3H-isobenzofuran-1(3H)-one (dithienylphthalide, 8). The same procedure is applied to obtain 1,3-dithienyl-4,5,6,7-tetradeuterioisothianaphthene (10b) and 1,3-dithienyl-4,5,6,7-tetrafluoroisothianaphthene (10c). The synthesis of the 2,3-dithienoylpyridine (12a), 3,4-dithienoylpyridine (12b), and 2,3-dithienoylpyrazine (12c) however fails. The presence of nitrogen in the central ring system influences the result of the Grignard reaction. Possibly the free electron pair of the nitrogen interferes with the formation of a stable six-membered ring intermediate which is essential for the diketone formation.