3,6-dimethyl-5-(methylthio)imidazo<4,5-d>isothiazole | 169694-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: 3,6-dimethyl-5-(methylthio)imidazo<4,5-d>isothiazole
• 英文别名: 3,6-Dimethyl-5-methylsulfanylimidazo[4,5-d][1,2]thiazole
• CAS: 169694-63-7
• 化学式: C₇H₉N₃S₂
• 分子量: 199.301
• InChiKey: WIRSQEWBLZJJPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dimethyl-5-(methylthio)imidazo<4,5-d>isothiazole 在 Oxone 、 silica gel 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以58%的产率得到3,6-dimethyl-5-methanesulfonylimidazo<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-methyl-5-(N-methylamino)-4-nitroisothiazole 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 3,6-dimethyl-5-(methylthio)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

文献信息

• 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
  作者：Eric E. Swayze、Leroy B. Townsend

  DOI：10.1021/jo00125a016

  日期：1995.10

  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.