ethyl 5,7-diphenyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate | 154867-04-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 5,7-diphenyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate
• 英文别名: ethyl 3-oxo-5,7-diphenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 3-oxo-5,7-diphenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 3-oxo-5,7-diphenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 154867-04-6
• 化学式: C₂₁H₁₈N₂O₃S
• 分子量: 378.452
• InChiKey: PFFGULJWAJPQBF-UHFFFAOYSA-N

物化性质

• 沸点：
  541.6±60.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-chlorobenzenediazonium chloride 、 ethyl 5,7-diphenyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到ethyl 2,3-dioxo-2-(4-chlorophenylhydrazono)-5,7-diphenyl-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-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：

  苯甲酰乙酸乙酯 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 5,7-diphenyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-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

文献信息

• Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase
  作者：Dan Zhao、Chen Chen、Huayong Liu、Likang Zheng、Yao Tong、Di Qu、Shiqing Han

  DOI：10.1016/j.ejmech.2014.09.096

  日期：2014.11

  With an intention to potent inhibitors of YycG histidine kinase, a series of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives were synthesized and evaluated for their antibacterial, antibiofilm and hemolytic activities. The majority of the compounds showed good activity against Staphylococcus epidermidis and Staphylococcus aureus, with MIC values of 1.56-6.25 mu M, simultaneously presented promising antiobifilm activity against S. epidermidis ATCC35984 at 50 mu M. The test of inhibitory activity on YycG kinase suggested the antibacterial activities of these derivatives are based on inhibiting the enzyme activity of the YycG HK domain. The hemolytic activity test suggested these compounds exhibited in vitro antibacterial activity at non-hemolytic concentrations. (c) 2014 Elsevier Masson SAS. All rights reserved.
• 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.