5-(4-methylphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-methylphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester
• 英文别名: ethyl 7-methyl-5-(4-methylphenyl)-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• 化学式: C₁₇H₁₈N₂O₃S
• 分子量: 330.408
• InChiKey: YHAGIQWOOKVRKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  5-(4-methylphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 在 sodium tetrahydroborate 、 vanadia 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 75.0h， 生成 ethyl 1-(4-bromophenyl)-3-(hydroxymethyl)-7-methyl-5-(4-methylphenyl)-1,5-dihydro[1,2,4]triazolo[4,3-a]-pyrimidine-6-carboxylate
  参考文献：
  名称：

  C = N键还原引起的噻唑并[3,2-a]嘧啶重排为三唑并[4,3-a]嘧啶

  摘要：

  通过还原5,6,7-三取代的2-（芳基肼基亚基）-5 H- [1,3]噻唑并[3,2 - a ]-嘧啶-3（2 ）制备三唑并[4,3- a ]嘧啶在室温下在V 2 O 5存在下用NaBH 4形成H）一。乙基3-（羟甲基）-5-（4-甲氧基苯基）-7-甲基-1-苯基-1,5-二氢[1,2,4]三唑并[4,3 - a ]嘧啶-6-的结构通过单晶X射线衍射数据证明了羧酸盐。讨论了包括过渡笼结构在内的反应机理。

  DOI：

  10.1007/s10593-019-02604-4
• 作为产物：
  描述：

  氯乙酰氯 、 5-carboethoxy-6-methyl-4-(4-methylphenyl)-1H-pyrimidin-2-thione 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以85%的产率得到5-(4-methylphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Some Bicyclic Thiazolo- and Oxothiazolo-Pyrimidines

  摘要：

  Oxothiazolopyrimidine compounds 2(a-e) were synthesized under reflux condition, by a simple one-pot condensation reaction of the pyrimidine derivative 1 and chloroacetylchloride in the presence of silver acetate as a catalyst. In a similar way the thiazolopyrimidine 3 and oxothiazolopyrimidine 4 were synthesized by reaction of pyrimidine derivative 1 with 1,2-dibromoethane and 2-bromopropanoic acid respectively. The yields of products following recrystallization from ethanol were of the order of 55-89%.

  DOI：

  10.1080/104265090508406

文献信息

• Pathak, Arun; Narayanaswamy, Venugopala Katharigatta; Joshi, Aakanksha, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 273 - 276
  作者：Pathak, Arun、Narayanaswamy, Venugopala Katharigatta、Joshi, Aakanksha、Rao, Gopal Krishna、Devi, Kalpana

  DOI：——

  日期：——
• Synthesis Of Novel 5-Methylindeno[2,1E][1,3]Thiazolo[3,2-A]Pyrimidine-1,6(2H,10bH)-Diones
  作者：Akbar Mobinikhaledi、Amir Jafari

  DOI：10.1515/hc.2009.15.5.351

  日期：2009.1

  Treatment of ethyl 5-aryl-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 1(a-h), with aluminum chloride and acetyl chloride in nitrobenzene gave the corresponding 5-Methylindeno[2,1-e][1,3]thiazolo[3,2-a]pyrimidine-1,6(2H,10bH)-dione derivatives 2(a-h). Yields of the products, after recrystallizing with acetic acid, were of the order of 46-67%. H-1-NMR and C-13-NMR spectroscopy, and elemental analysis were used for identification of these compounds.
• Structure and Biological Properties of 2-Phenylhydrazone Derivatives of Thiazolopyrimidines
  作者：A. S. Agarkov、E. R. Gabitova、F. B. Galieva、A. S. Ovsyannikov、A. D. Voloshina、A. K. Shiryaev、I. A. Litvinov、S. E. Solovieva、I. S. Antipin

  DOI：10.1134/s0012500822030016

  日期：2022.3
• Rearrangement of thiazolo[3,2-a]pyrimidines into triazolo[4,3-a]pyrimidines induced by C=N bond reduction
  作者：Eugenia A. Lashmanova、Artem S. Agarkov、Victor B. Rybakov、Andrey K. Shiryaev

  DOI：10.1007/s10593-019-02604-4

  日期：2019.12

  Triazolo[4,3-a]pyrimidines were prepared by the reduction of 5,6,7-trisubstituted 2-(arylhydrazinylidene)-5H-[1,3]thiazolo[3,2-a]- pyrimidin-3(2H)-ones with NaBH4 in the presence of V2O5 at room temperature. The structure of ethyl 3-(hydroxymethyl)- 5-(4-methoxyphenyl)-7-methyl-1-phenyl-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate was proven by the single crystal X-ray diffraction data

  通过还原5,6,7-三取代的2-（芳基肼基亚基）-5 H- [1,3]噻唑并[3,2 - a ]-嘧啶-3（2 ）制备三唑并[4,3- a ]嘧啶在室温下在V 2 O 5存在下用NaBH 4形成H）一。乙基3-（羟甲基）-5-（4-甲氧基苯基）-7-甲基-1-苯基-1,5-二氢[1,2,4]三唑并[4,3 - a ]嘧啶-6-的结构通过单晶X射线衍射数据证明了羧酸盐。讨论了包括过渡笼结构在内的反应机理。
• Synthesis of Some Bicyclic Thiazolo- and Oxothiazolo-Pyrimidines
  作者：A. Mobinikhaledi、N. Foroughifar、B. Ahmadi

  DOI：10.1080/104265090508406

  日期：2005.2

  Oxothiazolopyrimidine compounds 2(a-e) were synthesized under reflux condition, by a simple one-pot condensation reaction of the pyrimidine derivative 1 and chloroacetylchloride in the presence of silver acetate as a catalyst. In a similar way the thiazolopyrimidine 3 and oxothiazolopyrimidine 4 were synthesized by reaction of pyrimidine derivative 1 with 1,2-dibromoethane and 2-bromopropanoic acid respectively. The yields of products following recrystallization from ethanol were of the order of 55-89%.