2,3-dihydro-5-methyl-7-phenyl-imidazo[5,1-b]thiazole | 659738-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-dihydro-5-methyl-7-phenyl-imidazo[5,1-b]thiazole
• 英文别名: 5-Methyl-7-phenyl-2,3-dihydroimidazo[5,1-b][1,3]thiazole
• CAS: 659738-72-4
• 化学式: C₁₂H₁₂N₂S
• 分子量: 216.307
• InChiKey: IXUREUVFTRYZKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苯亚甲基苯磺酰胺 、 3-acetylthiazolidine-2-carboxylic acid 在 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 29.0h， 生成 2,3-dihydro-5-methyl-7-phenyl-imidazo[5,1-b]thiazole 、 cis-5-acetyl-3-phenyl-2-(phenylsulphonyl)-8-thia-2,5-diazaspiro[3,4]octan-1-one 、 trans-5-acetyl-3-phenyl-2-(phenylsulphonyl)-8-thia-2,5-diazaspiro[3,4]octan-1-one
  参考文献：
  名称：

  Synthesis of imidazo[5,1-b]thiazoles or spiro-β-lactams by reaction of imines with mesoionic compounds or ketenes generated from N-acyl-thiazolidine-2-carboxylic acids

  摘要：

  New mesoionic compounds (2H, 3H-thiazolo[3,2-c]oxazol-7-ones) (beta) or ketenes ((3-acyl-1,3-thiazolidin-2-ylidene)methanone) (beta') were generated from N-acetyl and N-benzoyl-thiazolidine-2-carboxylic acids (7a,b) using different methods, and their reactivity towards N-(phenylmethylene)benzenesulfonamide (2) and N-(phenylmethylene)aniline (3) was tested. When (7a,b) were treated with (2) and acetic anhydride in refluxing toluene solution, only imidazo[5,1-b]thiazoles (8a,b) were obtained from the mesoionic compound intermediates (beta). When the ketene intermediates (beta') were generated from (7a,b) by means of Mukaiyama's reagent, only spiro-beta-lactams (9a,b) were isolated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.093

文献信息

• Synthesis of imidazo[5,1-b]thiazoles or spiro-β-lactams by reaction of imines with mesoionic compounds or ketenes generated from N-acyl-thiazolidine-2-carboxylic acids
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Concetta La Rosa

  DOI：10.1016/j.tet.2003.10.093

  日期：2004.1

  New mesoionic compounds (2H, 3H-thiazolo[3,2-c]oxazol-7-ones) (beta) or ketenes ((3-acyl-1,3-thiazolidin-2-ylidene)methanone) (beta') were generated from N-acetyl and N-benzoyl-thiazolidine-2-carboxylic acids (7a,b) using different methods, and their reactivity towards N-(phenylmethylene)benzenesulfonamide (2) and N-(phenylmethylene)aniline (3) was tested. When (7a,b) were treated with (2) and acetic anhydride in refluxing toluene solution, only imidazo[5,1-b]thiazoles (8a,b) were obtained from the mesoionic compound intermediates (beta). When the ketene intermediates (beta') were generated from (7a,b) by means of Mukaiyama's reagent, only spiro-beta-lactams (9a,b) were isolated. (C) 2003 Elsevier Ltd. All rights reserved.