6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo<2,1-b><1,3>-thiazole | 113991-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo<2,1-b><1,3>-thiazole
• 英文别名: 6-(4-chlorophenyl)-2-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole；Imidazo[2,1-b]thiazole, 6-(4-chlorophenyl)-3-methyl-5-nitroso-；6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole
• CAS: 113991-07-4
• 化学式: C₁₂H₈ClN₃OS
• 分子量: 277.734
• InChiKey: QPAZMLMOLMLWFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo<2,1-b><1,3>-thiazole 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 8-(4-chlorophenyl)-8-hydroxy-5-methyl-8H-<1,4>thiazino<3,4-c><1,2,4>oxadiazol-3-one
  参考文献：
  名称：

  A new ring transformation: conversion of 6-p-chlorophenyl-3-methyl-5-nitrosoimidazo[2,1-b]thiazole into 8-p-chlorophenyl-8-hydroxy-5-methyl-3-oxo-1,2,4-oxadiazolo[3,4-c][1,4-]thiazine by the action of mineral acids

  摘要：

  6-对氯苯基-3-甲基-5-亚硝基咪唑并[2;1-b]噻唑1在室温下用稀盐酸在二恶烷中处理得到8-对氯苯基-8-羟基-5-甲基-3- oxo-1,2,4-恶二唑并[3,4-c][1,4]噻嗪2，含有新的稠环体系，其分子结构通过物理方法（1H和13C NMR、电子碰撞质量和红外光谱，以及 XRD）。

  DOI：

  10.1039/c39920001394

文献信息

• Ring–ring interconversion: the rearrangement of 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole into 8-(4-chlorophenyl)-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-one. Elucidation of the reaction product through spectroscopic and X-ray crystal structure analysis
  作者：Aldo Andreani、Roberta Billi、Barbara Cosimelli、Angelo Mugnoli、Mirella Rambaldi、Domenico Spinelli

  DOI：10.1039/a701909b

  日期：——

  The reactivity of 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole (a member of a class of mutagenic compounds) with hydrochloric acid in ethanol has been investigated and the nature of the reaction product unambiguously established on the basis of infrared, NMR and mass spectra and a crystal structure determination.

  研究了6-（4-氯苯基）-3-甲基-5-亚硝基磺并咪唑[2,1- b ] [1,3]噻唑（一种致突变化合物的成员）与盐酸在乙醇中的反应性，并对其进行了研究。反应产物的性质基于红外，NMR和质谱以及晶体结构的确定而明确地确定。
• Ring-ring interconversions. Part 3. On the effect of the substituents on the thiazole moiety in the ring-opening/ring-closing reactions of nitrosoimidazo[2,1-<i>b</i>][1,3]thiazoles with hydrochloric acid
  作者：Roberta Billi、Barbara Cosimelli、Domenico Spinelli、Alberto Leoni

  DOI：10.1002/jhet.5570370433

  日期：2000.7

  The reaction of 6-(4-chlorophenyl)-5-nitrosoimidazo[2,1-b][1,3]thiazole 1b, 6-(4-chlorophenyl)-2-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole 1c, 6-(4-chlorophenyl)-2,3-dimethyl-5-nitrosoimidazo-[2,1-b][1,3]thiazole 1d and 2-(4-chlorophenyl)-3-nitrosobenzo[d]imidazo[2,1-b][1,3]thiazole 1e with hydrochloric acid has been carried out in order to investigate the effect of substituents on the thiazole ring

  6-（4-氯苯基）-5-硝基磺酰咪唑[2,1- b ] [1,3]噻唑1b，6-（4-氯苯基）-2-甲基-5-硝基磺酰咪唑[2,1- b]的反应] [1,3]噻唑1c，6-（4-氯苯基）-2,3-二甲基-5-亚硝基磺酰胺基-[2,1- b ] [1,3]噻唑1d和2-（4-氯苯基）-为了研究取代基在最近报道的环-环互变反应中对噻唑环的作用，已经进行了3-亚硝基苯并[ d ]咪唑并[2，1- b ] [1，3]噻唑1e与盐酸的反应。在每种情况下，相应的[1,4]-噻嗪[3,4- c ] [1,2,4]恶二唑-3-酮2b-e已获得。特别是，苯并衍生物1e提供了4-（4-氯苯基）-4-羟基-4 H-苯并[5,6] [1,4]噻嗪基[3,4- c ] [1,2,4]恶二唑-1-one 2e，包含一个新的具有拟平面几何形状的三环系统，其药理学潜力似乎是有希望的。
• Ring-ring interconversions. Part 2. Effect of the substituent on the rearrangement of 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles into 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-ones. A novel class of potential antitumor agents
  作者：Roberta Billi、Barbara Cosimelli、Domenico Spinelli、Mirella Rambaldi

  DOI：10.1016/s0040-4020(99)00189-1

  日期：1999.4

  The reaction of several 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles with hydrochloric acid by refluxing in ethanol gives new 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c] [1,2,4]oxadiazol-3-ones for testing of their biological activity. By carrying out the reaction at room temperature it has been possible to isolate reaction intermediates to which structures have been assigned. This study has provided information on the reaction mechanism and on the effect of the substituent in the phenyl ring on the yield of the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.