3-phenylthiazolo<4,5-d>pyrimidine-2,7(6H)-dione | 150455-46-2

• 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: 3-phenylthiazolo<4,5-d>pyrimidine-2,7(6H)-dione
• 英文别名: Baqaphhhyneidg-uhfffaoysa-；3-phenyl-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione
• CAS: 150455-46-2
• 化学式: C₁₁H₇N₃O₂S
• 分子量: 245.261
• InChiKey: BAQAPHHHYNEIDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenylthiazolo<4,5-d>pyrimidine-2,7(6H)-dione 在 sodium hydroxide 、 sodium dithionite 、 air 作用下， 反应 21.0h， 生成 5-Methylsulfanyl-6-phenylamino-3H-pyrimidin-4-one
  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
• 作为产物：
  描述：

  7-Oxo-3-phenylthiazolo<4,5-d>pyrimidin-2-thion 在 水 、 硫酸二甲酯 作用下， 以93%的产率得到3-phenylthiazolo<4,5-d>pyrimidine-2,7(6H)-dione
  参考文献：
  名称：

  Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione

  摘要：

  Treatment of 7-oxo-3-phenylthiazolo[4,5-d]-pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).

  DOI：

  10.3987/com-92-6230

文献信息

• 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：——
• Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione
  作者：Katsuhiko Nagahara、Masae Sekine、Atsushi Takada、Howard B. Cottam、Roland K. Robins

  DOI：10.3987/com-92-6230

  日期：——

  Treatment of 7-oxo-3-phenylthiazolo[4,5-d]-pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).
• 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