5-acetamido-4-nitroisothiazole-3-carboxylic acid | 153970-43-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-acetamido-4-nitroisothiazole-3-carboxylic acid
• 英文别名: 5-Acetamido-4-nitro-1,2-thiazole-3-carboxylic acid
• CAS: 153970-43-5
• 化学式: C₆H₅N₃O₅S
• 分子量: 231.189
• InChiKey: DDEFOJNDZYLTKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-acetamido-4-nitroisothiazole-3-carboxylic acid 在 氯化亚砜 、 氨 作用下， 生成 5-amino-4-nitroisothiazole-3-carboxamide
  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：

  5-acetamido-3-methyl-4-nitroisothiazole 在 chromium(VI) oxide 、 硫酸 作用下， 生成 5-acetamido-4-nitroisothiazole-3-carboxylic acid
  参考文献：
  名称：

  1337.异噻唑。第九部分 异噻唑并嘧啶

  摘要：

  DOI：

  10.1039/jr9650007277

文献信息

• The synthesis of several imidazo[4,5-<i>d</i>]isothiazoles. Derivatives of a new ring system
  作者：Eric E. Swayze、Leroy B. Townsend

  DOI：10.1002/jhet.5570300533

  日期：1993.10

  the new imidazo[4,5-d]isothiazole ring system have been synthesized from the appropriately substituted isothiazolediamines. The reaction of 3-methyl-4,5-diaminoisothiazole (4a) with diethoxy-methyl acetate gave a low yield of 3-methylimidazo[4,5-d]isothiazole (5a). However, the analogous reaction of 4,5-diaminoisothiazole (4b) with diethoxymethyl acetate failed to yield the parent imidazo[4,5-d]isothiazole

  从适当取代的异噻唑二胺合成了新的咪唑并[4,5- d ]异噻唑环系的几种衍生物。3-甲基-4,5-二氨基异噻唑（4a）与二乙氧基乙酸甲酯的反应产生了低产率的3-甲基咪唑并[4,5- d ]异噻唑（5a）。然而，4，5-二氨基异噻唑（4b）与二乙氧基甲基乙酸酯的类似反应未能产生母体咪唑并[4，5- d ]异噻唑环系统。二胺4a和4b易于与硫代羰基二咪唑环合，得到不稳定的硫酮6a和6b，它们被烷基化了原位得到相应的5-甲基硫代咪唑并[4，5- d ]异噻唑7a和7b的良好产率。通过用阮内镍处理，这些化合物都不能还原为相应的5-未取代的衍生物。据我们所知，这是咪唑并[4,5- d ]异噻唑环系统的首次报道。