ethyl 3-amino-2-cyano-5-(4-methoxyphenyl)-7-methyl-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate | 154866-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-amino-2-cyano-5-(4-methoxyphenyl)-7-methyl-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate
• 英文别名: ethyl 3-amino-2-cyano-5-(4-methoxyphenyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 3-amino-2-cyano-5-(4-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 154866-95-2
• 化学式: C₁₈H₁₈N₄O₃S
• 分子量: 370.432
• InChiKey: NTKPGOKDFUDETA-UHFFFAOYSA-N

物化性质

• 沸点：
  549.0±60.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-2-cyano-5-(4-methoxyphenyl)-7-methyl-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate 在 盐酸羟胺 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以60%的产率得到ethyl 3-amino-8-(4-methoxyphenyl)-6-methyl-1H,8H-pyrazolo<3,4-d>thiazolo<3,2-a>pyrimidine-7-carboxylate
  参考文献：
  名称：

  A convenient synthesis of thiazolopyrimidines, thiazolodipyrimidines and heterocyclothiazolopyrimidines

  摘要：

  Ethyl 4-aryl-6-substituted-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 1 reacted with bromomalononitrile (2) to give ethyl 3-amino-5-aryl-2-cyano-7-substituted-5H-thiazolo(3,2-a]pyrimidine-6-carboxylates 3. The latter compounds reacted with formic acid, hydroxylamine hydrochloride and with formamide to give 9H-3,4-dihydrothiazolo[3,2-a:4,5-b]pyrimidine-8-carboxylates 5, 1H,8H-pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidine-7-carboxylates 8 and 2,7-diaminothiazolo[4,5-d]pyrimidine (7), respectively. Compounds 1b,e reacted with chloroacetyl chloride to yield ethyl 5-aryl-3-oxo-7-substituted-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates 9a,b which coupled with arenediazonium chlorides to give the corresponding 2-arylhydrazone derivatives 10a,b. Compound 9a adds is-proportional-to-cyanocinnamonitriles 12a-c to yield ethyl 2-amino-4-aryl-3-cyano-9-(4-methoxyphenyl)-7-methyl-4H,9H-pyrano[2,3-d]thiazolo[3,2-a]pyrimidine-8-carboxylates 13a-c. Refluxing 1b-d with phenacyl bromide produced ethyl 5-aryl-7-methyl-3-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates 14a-c.

  DOI：

  10.1016/s0040-4020(01)80225-8
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 生成 ethyl 3-amino-2-cyano-5-(4-methoxyphenyl)-7-methyl-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate
  参考文献：
  名称：

  一些具有潜在抗氧化和抗菌活性的新型噻唑并嘧啶、噻唑二嘧啶和噻唑并嘧啶并噻唑并嘧啶衍生物的微波辅助合成

  摘要：

  乙酰乙酸乙酯、硫脲和适当的芳香醛的 Biginelli 反应用于生产 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylates，它与溴丙二腈反应生成得到 3-氨基-5-芳基-2-氰基-7-甲基-5H-噻唑并[3,2-a]嘧啶-6-羧酸乙酯，而不是异构的7H-噻唑并[3,2-a]嘧啶。噻唑并嘧啶衍生物与二硫化碳反应生成乙基 9-芳基-7-甲基-2,4-二硫代-2,3,4,9-四氢-1H-噻唑并[3,2-a:4,5-d'] dipyrimidine-8-carboxylates，与苯甲酰溴反应生成乙基 8-methyl-10-(4-methoxyphenyl)-3-located-5-thioxo-2(un)subatituded-10H-thiazolo[3'',2' ':1',2']pyrimido[4',5':4

  DOI：

  10.3390/molecules17089652

文献信息

• A convenient synthesis of thiazolopyrimidines, thiazolodipyrimidines and heterocyclothiazolopyrimidines
  作者：Sherif M. Sherif、Mohamed M. Youssef、Khaled M. Mobarak、Abdel-Samei M. Abdel-Fattah

  DOI：10.1016/s0040-4020(01)80225-8

  日期：——

  Ethyl 4-aryl-6-substituted-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 1 reacted with bromomalononitrile (2) to give ethyl 3-amino-5-aryl-2-cyano-7-substituted-5H-thiazolo(3,2-a]pyrimidine-6-carboxylates 3. The latter compounds reacted with formic acid, hydroxylamine hydrochloride and with formamide to give 9H-3,4-dihydrothiazolo[3,2-a:4,5-b]pyrimidine-8-carboxylates 5, 1H,8H-pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidine-7-carboxylates 8 and 2,7-diaminothiazolo[4,5-d]pyrimidine (7), respectively. Compounds 1b,e reacted with chloroacetyl chloride to yield ethyl 5-aryl-3-oxo-7-substituted-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates 9a,b which coupled with arenediazonium chlorides to give the corresponding 2-arylhydrazone derivatives 10a,b. Compound 9a adds is-proportional-to-cyanocinnamonitriles 12a-c to yield ethyl 2-amino-4-aryl-3-cyano-9-(4-methoxyphenyl)-7-methyl-4H,9H-pyrano[2,3-d]thiazolo[3,2-a]pyrimidine-8-carboxylates 13a-c. Refluxing 1b-d with phenacyl bromide produced ethyl 5-aryl-7-methyl-3-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates 14a-c.
• Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity
  作者：Mohamed M. Youssef、Mahmoud A. Amin

  DOI：10.3390/molecules17089652

  日期：——

  assisted method is preferable because of the time reduction and yield improvements achieved. The new compounds were tested for their biological activity as antioxidants, antibacterial or antifungal agents. Some of the new compounds were found to have moderate to good antioxidant and antimicrobial activities.

  乙酰乙酸乙酯、硫脲和适当的芳香醛的 Biginelli 反应用于生产 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylates，它与溴丙二腈反应生成得到 3-氨基-5-芳基-2-氰基-7-甲基-5H-噻唑并[3,2-a]嘧啶-6-羧酸乙酯，而不是异构的7H-噻唑并[3,2-a]嘧啶。噻唑并嘧啶衍生物与二硫化碳反应生成乙基 9-芳基-7-甲基-2,4-二硫代-2,3,4,9-四氢-1H-噻唑并[3,2-a:4,5-d'] dipyrimidine-8-carboxylates，与苯甲酰溴反应生成乙基 8-methyl-10-(4-methoxyphenyl)-3-located-5-thioxo-2(un)subatituded-10H-thiazolo[3'',2' ':1',2']pyrimido[4',5':4