3-methyl-4-nitro-5-isothiazole | 169694-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-4-nitro-5-isothiazole
• 英文别名: N-benzyl-3-methyl-4-nitro-1,2-thiazol-5-amine
• CAS: 169694-44-4
• 化学式: C₁₁H₁₁N₃O₂S
• 分子量: 249.293
• InChiKey: KKANWWLBCBHLHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-4-nitro-5-isothiazole 在 盐酸 、 sodium hydroxide 、 铁粉 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 2.5h， 生成 3-methyl-5-(methylthio)-6-(phenylmethyl)imidazo<4,5-d>isothiazole
  参考文献：
  名称：

  The Synthesis of Substituted Imidazo[4,5-d]isothiazoles via the Ring Annulation of Isothiazole Diamines: An Investigation of the Chemical, Physical, and Biological Properties of Several Novel 5:5 Fused Analogs of the Purine Ring System

  摘要：

  A series of imidazo[4,5-d]isothiazoles have been prepared from isothiazole precursors via a strategy employing ring annulation of the appropriate isothiazole diamine. In this manner, several 4,5-diaminoisothiazoles were converted into the corresponding 5-(alkylthio)imidazo[4,5-d]isothiazoles via a two-step, one-pot procedure in good yield. This methodology proved quite general and allows for the introduction of various substituents onto the 3-, 5-, and 6-positions of this ring system. Reaction with Raney nickel destroyed the ring system, presumably through removal of the sulfur at the 1-position, and the 5-mercapto substituent could not be removed selectively. Ring annulation with diethoxymethyl acetate provided the 5-unsubstituted imidazo[4,5-d]isothiazoles but was less general, and only the 3-methyl derivatives could be prepared. Imidazo[4,5-d]isothiazoles bearing no substituents on nitrogen readily underwent alkylation to afford mixtures of the N-4- and N-6-substituted compounds. The chemical and physical properties of these novel heterocycles were studied in detail, and the structure of 3-methyl-5-methanesulfonyl-6-(phenylmethyl)imidazo[4,5-d] isothiazole was verified by single crystal X-ray diffraction studies.

  DOI：

  10.1021/jo00125a016
• 作为产物：
  描述：

  3-甲基-4-硝基-1,2-噻唑-5-胺 、 溴甲苯 在 sodium hydride 作用下， 以 乙腈 、 paraffin 为溶剂， 以83%的产率得到3-methyl-4-nitro-5-isothiazole
  参考文献：
  名称：

  The Synthesis of Substituted Imidazo[4,5-d]isothiazoles via the Ring Annulation of Isothiazole Diamines: An Investigation of the Chemical, Physical, and Biological Properties of Several Novel 5:5 Fused Analogs of the Purine Ring System

  摘要：

  A series of imidazo[4,5-d]isothiazoles have been prepared from isothiazole precursors via a strategy employing ring annulation of the appropriate isothiazole diamine. In this manner, several 4,5-diaminoisothiazoles were converted into the corresponding 5-(alkylthio)imidazo[4,5-d]isothiazoles via a two-step, one-pot procedure in good yield. This methodology proved quite general and allows for the introduction of various substituents onto the 3-, 5-, and 6-positions of this ring system. Reaction with Raney nickel destroyed the ring system, presumably through removal of the sulfur at the 1-position, and the 5-mercapto substituent could not be removed selectively. Ring annulation with diethoxymethyl acetate provided the 5-unsubstituted imidazo[4,5-d]isothiazoles but was less general, and only the 3-methyl derivatives could be prepared. Imidazo[4,5-d]isothiazoles bearing no substituents on nitrogen readily underwent alkylation to afford mixtures of the N-4- and N-6-substituted compounds. The chemical and physical properties of these novel heterocycles were studied in detail, and the structure of 3-methyl-5-methanesulfonyl-6-(phenylmethyl)imidazo[4,5-d] isothiazole was verified by single crystal X-ray diffraction studies.

  DOI：

  10.1021/jo00125a016