6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one | 175922-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• 英文别名: 6-{[phenylmethylene]amino}-2-thioxo-2,3-dihydropyrimidin-4(1H)-one；6-(benzylideneamino)-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 175922-28-8
• 化学式: C₁₁H₉N₃OS
• 分子量: 231.278
• InChiKey: HTWHKEPIYNDLDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 以70%的产率得到6-benzylidenamino-1(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  Nucleosides 7⁹: Synthesis, Structure, and Biological Activity of New 6-Arylidenamino-2-Thio- and 2-BenzylthiopyrimidineN-Nucleosides

  摘要：

  The condensation of 6-amino-2-thioxo-2,3-dihydro-1H-pyrimidine-4-one [compound (1)] with aromatic aldehydes (2) afforded azomethine derivatives (3). The formed azomethines underwent glycosidation with alpha-acetobromoglucose (4) to form the corresponding pyrimidine N-glycosides (6) and not S-glycosides (5). The interaction of (3) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-beta-D-ribofuranose (8) afforded the corresponding pyrimidine N-riboside (10) and not S-riboside (9). Deacetylation and debenzoylation of each of (6) and (10) by using Methanolic sodium methoxide afforded the corresponding free N-nucleosides (7) and (11), respectively. Next, the reaction of 2-benzylthio-6-benzylidenaminouracil (13) with (4) and (8) did not yield the corresponding protected N-nucleosides (14) and (17), whereas it afforded (15) and (18), respectively. The latter compounds (15) and (18) were stirred in methanolic sodium methoxide to yield the corresponding free N-nucleosides (16) and (19), respectively. The structures of products have been elucidated and reported and also some of the products were screened for their antimicrobial activity.

  DOI：

  10.1080/15257770.2011.597628
• 作为产物：
  描述：

  6-氨基-2-硫脲嘧啶 、 苯甲醛 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以88%的产率得到6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  合成某些作为抗菌剂和抗炎剂的嘧啶衍生物。

  摘要：

  通过6-氨基-2-硫代-1H-嘧啶-4-酮(1)与不同试剂反应得到多种新型双环和三环嘧啶衍生物。测试了一些合成化合物的抗菌和抗炎活性。

  DOI：

  10.3390/molecules15031882

文献信息

• Convenient Methodology for Some Heterocyclization Reactions with Thioxopyrimidine Derivatives
  作者：K. M. El-Mahdy、O. Farouk

  DOI：10.1134/s1070428020110172

  日期：2020.11

  6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one has been used as a versatile building block for the synthesis of thioxopyrimidine derivatives. A variety of novel fused pyrimidines has been prepared via nucleophilic and/or electrophilic reactions of thioxopyrimidine derivatives. The structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data.

  摘要 开发了一种简单有效的嘧啶核衍生化方法。易于获得的6-氨基-2-硫代-2-3，3-二氢嘧啶-4（1 H）-1已被用作合成硫代嘧啶衍生物的通用结构单元。已经通过硫代嘧啶衍生物的亲核和/或亲电反应制备了多种新颖的稠合嘧啶。根据元素分析和光谱数据推导了新合成产物的结构。
• Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity
  作者：M. E. A. Khalifa、M. A. Amin、M. A. N. Mosselhi

  DOI：10.1134/s1068162014010075

  日期：2014.1

  Reaction of hydrazonoyl halides with 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and 2,3-diaminoquinazolin-4-one site-selectively afforded 3-substituted-7-(benzylidenamino)-1-phenyl-[1,2,4]triazolo[4,3-a]-pyrimidin-5(1H)-ones, [1,2,4,5]tetrazino[6,1-b]quinazolin-6(4H)-one, and 3-methyl-2-(4-substituted-phenylhydrazo)-[1,2,4]triazino[3,2-b]quinazolin-10-ones in good yields. The structures

  腙酰卤与 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 和 2,3-diaminoquinazolin-4-one 反应位点选择性地提供 3-取代-7-(benzylidenamino) )-1-苯基-[1,2,4]三唑并[4,3-a]-嘧啶-5(1H)-酮，[1,2,4,5]四嗪基[6,1-b]喹唑啉- 6(4H)-one 和 3-甲基-2-(4-取代-苯基肼基)-[1,2,4] 三嗪基 [3,2-b]quinazolin-10-ones 收率良好。通过化学证据及其 IR、1H、13C NMR 和 MS 光谱阐明了新合成化合物的结构。此外，一些产品针对不同的细菌和真菌菌株进行了筛选。