9-chloro-7H-benzo[d]benzoimidazo[2,1-b][1,3]thiazine | 1353998-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 9-chloro-7H-benzo[d]benzoimidazo[2,1-b][1,3]thiazine
• 英文别名: 3-chloro-5H-benzimidazo[1,2-a][3,1]benzothiazine；3-chloro-5H-benzimidazolo[1,2-a][3,1]benzothiazine
• CAS: 1353998-89-6
• 化学式: C₁₄H₉ClN₂S
• 分子量: 272.758
• InChiKey: PWAKQCKSXOCALX-UHFFFAOYSA-N

物化性质

• 沸点：
  495.2±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-溴-5-氯苯甲醇 在 potassium phosphate 、 copper(l) iodide 、 potassium hydroxide 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 9-chloro-7H-benzo[d]benzoimidazo[2,1-b][1,3]thiazine
  参考文献：
  名称：

  Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates

  摘要：

  The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with beta-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.071

文献信息

• Imidazobenzothiazine and primidobenzothiazine derivatives synthesis via an aliphatic SN2 substitution/Cu(I) catalyzed Ullmann coupling cascade process
  作者：Ruihong Wang、Weixing Qian、Weiliang Bao

  DOI：10.1016/j.tetlet.2011.11.072

  日期：2012.1

  method for the preparation of various imidazobenzothiazine and primidobenzothiazine derivatives from readily available 2-mercaptoimidazoles (thiouracils) and bromobenzyl bromides via a copper(I)-catalyzed one-pot cascade process has been developed. The reaction involves a SN2 process and an intramolecular C–N cross coupling cyclization.

  已经开发了一种有效的方法，该方法通过铜（I）催化的一锅级联方法，从易于获得的2-巯基咪唑（硫尿嘧啶）和溴苄基溴化物中制备各种咪唑并苯并噻嗪衍生物和苄基苯并噻嗪衍生物。该反应涉及一个S N 2过程和一个分子内C–N交叉偶联环化反应。
• Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates
  作者：Mohamed A. Omar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1016/j.tet.2014.06.071

  日期：2014.9

  The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with beta-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained. (C) 2014 Elsevier Ltd. All rights reserved.