6-acetyl-7-methyl-5-(4-methoxyphenyl)-2H-thiazolo[3,2-a]pyrimidine-3(5H)-one | 357269-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-acetyl-7-methyl-5-(4-methoxyphenyl)-2H-thiazolo[3,2-a]pyrimidine-3(5H)-one
• 英文别名: 6-acetyl-5-(4-methoxyphenyl)-7-methyl-2H-thiazolo[3,2-a]pyrimidin-3(5H)-one；6-Acetyl-5-(4-methoxyphenyl)-7-methyl-2H,5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one；6-acetyl-5-(4-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one
• CAS: 357269-94-4
• 化学式: C₁₆H₁₆N₂O₃S
• 分子量: 316.381
• InChiKey: UHXPEZRFMUNYBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  6-acetyl-7-methyl-5-(4-methoxyphenyl)-2H-thiazolo[3,2-a]pyrimidine-3(5H)-one 在 劳森试剂 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以34%的产率得到(2E)-6-acetyl-2-[6-acetyl-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-2(3H)-ylidene]-5-(4-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one
  参考文献：
  名称：

  Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

  摘要：

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.014
• 作为产物：
  描述：

  氯乙酸乙酯 、 5-acetyl-4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine 在 氨 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以42%的产率得到6-acetyl-7-methyl-5-(4-methoxyphenyl)-2H-thiazolo[3,2-a]pyrimidine-3(5H)-one
  参考文献：
  名称：

  Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

  摘要：

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.014

文献信息

• Synthesis of thiazolo[3,2-a]pyrimidines based on 4-aryl-substituted 3,4-dihydro-pyrimidine(1H)-2-thiones and the crystal structure of ethyl 5-(2,4-dimethoxyphenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo-[3,2-a]pyrimidine-6-carboxylate
  作者：I. V. Kulakov、O. A. Nurkenov、D. M. Turdybekov、G. M. Issabaeva、A. S. Mahmutova、K. M. Turdybekov

  DOI：10.1007/s10593-009-0346-z

  日期：2009.7

  Thiazolo[3,2-a]pyrimidines were obtained in good yield by the reaction of 4-aryl-substituted 3,4-dihydropyrimidine(1H)-2-thiones and methyl chloroacetate in boiling toluene. Their structures were shown by 1H NMR spectroscopy and X-ray crystallography.

  通过使4-芳基取代的3，4-二氢嘧啶（1H）-2-硫酮与氯乙酸甲酯在沸腾的甲苯中反应，以高收率获得噻唑并[3，2- a ]嘧啶。它们的结构通过1 H NMR光谱和X射线晶体学显示。
• A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
  作者：Murugan Sathishkumar、Sangaraiah Nagarajan、Poovan Shanmugavelan、Murugan Dinesh、Alagusundaram Ponnuswamy

  DOI：10.3762/bjoc.9.78

  日期：——

  A rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impact of allylic strains in directing the regiocyclization has been noted.

  已经开发了一种快速高效的单锅无溶剂/清除剂合成2-亚氨基噻唑啉-4-酮的方案。有趣的是，区域/立体选择性合成只产生区异构体(Z)-3-烷基/芳基-2-(2-苯基环己-2-烯基亚氨基)噻唑啉-4-酮，收率良好。观察到的选择性是基于反应过程中产生的联烯应变相对大小的合理化。这是第一篇注意到联烯应变对定向区域环化的影响的报告。
• Intramolecular cyclization of 4-aryl-3,4-dihydropyrimidine- (1H)-2-thiones to give bicyclic thiazolo[3,2-a]pyrimidines
  作者：I. V. Kulakov

  DOI：10.1007/s10593-009-0374-8

  日期：2009.8
• Synthesis of new thiazolopyrimidines proceeding from 4-aryl-substituted 3,4-dihydropyrimidine-2(1H)-thiones
  作者：I. V. Kulakov

  DOI：10.1134/s1070428009080296

  日期：2009.8
• Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent
  作者：Eugenia A. Lashmanova、Anastasiya I. Kirdyashkina、Pavel A. Slepukhin、Andrey K. Shiryaev

  DOI：10.1016/j.tetlet.2018.02.014

  日期：2018.3

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.