ethyl 5-(4-methoxyphenyl)-2-(4-methoxyphenylmethylene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate | 154867-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-(4-methoxyphenyl)-2-(4-methoxyphenylmethylene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate
• 英文别名: ethyl 5-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 154867-09-1
• 化学式: C₂₅H₂₄N₂O₅S
• 分子量: 464.542
• InChiKey: VLRJIWVZYAZJKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-methoxyphenyl)-2-(4-methoxyphenylmethylene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以60%的产率得到ethyl 2-amino-3-cyano-4,9--7-methyl-4H,9H-pyrano<2,3-d>thiazolo<3,2-a>pyrimidine-8-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：

  2-巯基-4-(4-甲氧基苯基)-6-甲基-1,4-二氢嘧啶-5-羧酸乙酯 在 哌啶 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 5-(4-methoxyphenyl)-2-(4-methoxyphenylmethylene)-7-methyl-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

• 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.