InChI=1/C5H5N3S2/c1-8-4(7)3(2-6)10-5(8)9/h7H2,1H | 81403-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: InChI=1/C5H5N3S2/c1-8-4(7)3(2-6)10-5(8)9/h7H2,1H
• 英文别名: 4-amino-3-methyl-2-sulfanylidene-1,3-thiazole-5-carbonitrile
• CAS: 81403-18-1
• 化学式: C₅H₅N₃S₂
• mdl: MFCD09539367
• 分子量: 171.247
• InChiKey: FJFRYEKHLCSEOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  InChI=1/C5H5N3S2/c1-8-4(7)3(2-6)10-5(8)9/h7H2,1H 在 硫化氢 、 三乙胺 作用下， 以 吡啶 为溶剂， 反应 10.0h， 以75%的产率得到4-Amino-3-methyl-3-thioxo-Δ⁴-thiazolin-5-thiocarboxamid
  参考文献：
  名称：

  Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.

  摘要：

  6-Amino-thiazolo[4,5-c]isothiazole derivatives 4 are obtained by addition of hydrogen sulfide to the 4-Amino-thiazoline-5-carbonitrile 2 followed by cyclooxidation of the intermediate thioamides 3. In the presence of sodium sulfite the hydrolysis of the 4-amino-2-methylthio-thiazolium salts 5 derived from the title compounds 1 yields the 4-amino-thiazolin-2-ones 6. By their further hydrolysis the 2,4-dioxo-thiazolidin-5-carboxamides 8 are formed. The 2-oxo-and 2-thioxo-thiazolo [4,5-d]pyrimidin-7-ones and -thiones available from 1 undergo ring opening by hydrolysis to give the substituted 4-amino-6-oxo- and 4-amino-6-thioxo-pyrimidine-5-thiols 15a-h and 13i-e. They have been isolated as their disulfides 14 or 5-alkyl derivatives i.e. the substituted 4-amino-5-alkylthiopyrimidin-6-ones and -thiones 16. In analogy, the intermediate 6-amino-7-oxo-thiazolo[4,5-d] pyrimidin-2-thione 18 and the 7-amino-thiazolo[4,5-d]-pyrimidin-2-thione 24 derived from 1 react by ring cleavage to yield the 1,4- and 4,6-diamino-pyrimidin-5-thiole derivatives 22 and 27, respectively, isolated as their disulfides or alkylthio-derivatives. From the pyrimidine 16b the pyrimido[5,4-b]1,4-thiazine derivative 18 can be obtained.

  DOI：

  10.1007/bf00811521

文献信息

• Zur Chemie der 4-Aminothiazolin-2-thione
  作者：Karl Gewald、Ute Hain、Petra Hartung

  DOI：10.1007/bf00900005

  日期：1981.12
• Gewald K., Hain U., Schindler R., Gruner M., Monatsh. Chem, 125 (1994) N 10, S 1129-1143
  作者：Gewald K., Hain U., Schindler R., Gruner M.

  DOI：——

  日期：——
• GEWALD, K.;HAIN, U.;HARTUNG, P., MONATSH. CHEM., 1981, 112, N 12, 1393-1404
  作者：GEWALD, K.、HAIN, U.、HARTUNG, P.

  DOI：——

  日期：——
• Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.
  作者：K. Gewald、U. Hain、R. Schindler、M. Gruner

  DOI：10.1007/bf00811521

  日期：1994.10

  6-Amino-thiazolo[4,5-c]isothiazole derivatives 4 are obtained by addition of hydrogen sulfide to the 4-Amino-thiazoline-5-carbonitrile 2 followed by cyclooxidation of the intermediate thioamides 3. In the presence of sodium sulfite the hydrolysis of the 4-amino-2-methylthio-thiazolium salts 5 derived from the title compounds 1 yields the 4-amino-thiazolin-2-ones 6. By their further hydrolysis the 2,4-dioxo-thiazolidin-5-carboxamides 8 are formed. The 2-oxo-and 2-thioxo-thiazolo [4,5-d]pyrimidin-7-ones and -thiones available from 1 undergo ring opening by hydrolysis to give the substituted 4-amino-6-oxo- and 4-amino-6-thioxo-pyrimidine-5-thiols 15a-h and 13i-e. They have been isolated as their disulfides 14 or 5-alkyl derivatives i.e. the substituted 4-amino-5-alkylthiopyrimidin-6-ones and -thiones 16. In analogy, the intermediate 6-amino-7-oxo-thiazolo[4,5-d] pyrimidin-2-thione 18 and the 7-amino-thiazolo[4,5-d]-pyrimidin-2-thione 24 derived from 1 react by ring cleavage to yield the 1,4- and 4,6-diamino-pyrimidin-5-thiole derivatives 22 and 27, respectively, isolated as their disulfides or alkylthio-derivatives. From the pyrimidine 16b the pyrimido[5,4-b]1,4-thiazine derivative 18 can be obtained.

表征谱图