5-(3-nitrophenyl)-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-(3-nitrophenyl)-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-(3-nitrophenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• 化学式: C₁₆H₁₅N₃O₅S
• 分子量: 361.378
• InChiKey: LALZTPPCSRKZSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(3-nitrophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 在 aluminum (III) chloride 、 乙酰氯 作用下， 以 硝基苯 为溶剂， 以60%的产率得到5-methyl-9-nitroindeno[2,1-e][1,3]thiazolo[3,2-a]pyrimidine-1,6(2H,10bH)-dione
  参考文献：
  名称：

  Synthesis Of Novel 5-Methylindeno[2,1E][1,3]Thiazolo[3,2-A]Pyrimidine-1,6(2H,10bH)-Diones

  摘要：

  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.

  DOI：

  10.1515/hc.2009.15.5.351
• 作为产物：
  描述：

  ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate 、 氯乙酸 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以66%的产率得到5-(3-nitrophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Pathak, Arun; Narayanaswamy, Venugopala Katharigatta; Joshi, Aakanksha, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 273 - 276

  摘要：

  DOI：

文献信息

• New Method for the Preparation of 2,3-Disubstituted 2,3-Dihydrothiazolo[3,2-a]pyrimidines
  作者：A. S. Agarkov、A. A. Kozhikhov、A. A. Nefedova、A. S. Ovsyannikov、D. R. Islamov、S. E. Solovieva、I. S. Antipin

  DOI：10.1134/s0012500822700070

  日期：2022.8

  Abstract A new approach to the synthesis of 2,3-disubstituted 2,3-dihydrothiazolo[3,2-a]pyrimidines under microwave activation conditions has been developed. The method consists in the nucleophilic addition of methanol to 2-arylmethylidene derivatives of thiazolo[3,2-a]pyrimidine followed by intramolecular rearrangement to form 3,5-diaryl-2,3-dihydrothiazolo[3,2-a]pyrimidine-2,6-dicarboxylates.

  摘要 开发了一种在微波活化条件下合成 2,3-二取代 2,3-二氢噻唑并 [3,2 -a ] 嘧啶的新方法。该方法包括将甲醇亲核加成到噻唑并 [3,2- a ] 嘧啶的 2-芳基亚甲基衍生物，然后进行分子内重排以形成 3,5-二芳基-2,3-二氢噻唑并 [3,2- a ] 嘧啶- 2,6-二羧酸盐。
• (2-Hydroxy-3-Methoxybenzylidene)thiazolo[3,2-a]pyrimidines: Synthesis, Self-Assembly in the Crystalline Phase and Cytotoxic Activity
  作者：Artem S. Agarkov、Anna A. Nefedova、Elina R. Gabitova、Dilyara O. Mingazhetdinova、Alexander S. Ovsyannikov、Daut R. Islamov、Syumbelya K. Amerhanova、Anna P. Lyubina、Alexandra D. Voloshina、Igor A. Litvinov、Svetlana E. Solovieva、Igor S. Antipin

  DOI：10.3390/ijms24032084

  日期：——

  A series of new 2-hydroxy-3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with different aryl substituents at the 5 position are synthesized and characterized by 1H/ 13C NMR and IR-spectroscopy and mass-spectrometry, as well as single crystal X-ray diffraction (SCXRD). It was demonstrated that the type of hydrogen bonding can play a key role in the chiral discrimination of these compounds in the crystalline

  合成了一系列在 5 位具有不同芳基取代基的新型 2-羟基-3-甲氧基亚苄基噻唑并 [3,2-a] 嘧啶，并通过 1H/ 13C 核磁共振、红外光谱和质谱以及单晶表征X 射线衍射 (SCXRD)。事实证明，氢键的类型可以在结晶相中这些化合物的手性区分中发挥关键作用。OH...N 型氢键导致一维超分子异手性链或在形成纯手性链的情况下聚集结晶。OH...O 型氢键产生外消旋二聚体，它们以平行或成角度的二聚体排列方式填充到二维超分子层中。N...Br 或 O...Br 类型的卤素键合为结晶相中的超分子自组装带来了新的基序：形成一维超分子纯手性链而不是二维超分子层。进行了体外对多种肿瘤细胞的细胞毒性研究。结果发现，在 C5 碳原子上具有 3-硝基苯基取代基的 2-羟基-3-甲氧基亚苄基噻唑并 [3,2-a] 嘧啶显示出对 M-HeLa（宫颈腺癌）的高效率和对正常肝细胞的低细胞毒性。
• 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%.