3-(4-methoxyphenyl)[1,2,4]triazolo[3,4-b][1,3]benzothiazole | 19993-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 3-(4-methoxyphenyl)[1,2,4]triazolo[3,4-b][1,3]benzothiazole
• 英文别名: 3-(4-methoxyphenyl)benzo[4,5]thiazolo[2,3-c][1,2,4]triazole；3-(4-methoxy-phenyl)-benzo[4,5]thiazolo[2,3-c][1,2,4]triazole；3-(4-Methoxy-phenyl)-benzo[4,5]thiazolo[2,3-c][1,2,4]triazol；1-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3]benzothiazole
• CAS: 19993-97-6
• 化学式: C₁₅H₁₁N₃OS
• 分子量: 281.338
• InChiKey: HHNQTHMFEGWWGU-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 3-(4-methoxyphenyl)[1,2,4]triazolo[3,4-b][1,3]benzothiazole
  参考文献：
  名称：

  Photochemical Synthesis of s-Triazolo[3,4-b]benzothiazole and Mechanistic Studies on Benzothiazole Formation

  摘要：

  A general photochemical synthesis of s-triazolo[3,4-b]benzothiazoles from 4,5-disubstituted 1,2,4-triazole-3-thione is described. Steady photolysis, quantum yield determination, and laser flash photolysis experiments have been carried out. An intramolecular electron transfer mechanism has been proposed.

  DOI：

  10.1021/jo962190v

文献信息

• Convenient synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles with 1 mol% CuCl₂·2H₂O as catalyst in water
  作者：Li-Rong Wen、Shou-Lei Li、Jian Zhang、Ming Li

  DOI：10.1039/c4gc02156h

  日期：——

  A convenient and efficient procedure for the synthesis of benzo[4,5]thiazolo [2,3-c][1,2,4]triazoles has been developed via a tandem intermolecular C–N bond and intramolecular C–S bond formation sequence from o-bromo-arylisothiocyanates and aroylhydrazides. A series of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles were provided in excellent overall yields with 1 mol% CuCl2·2H2O/1 mol% 1,10-phenanthroline

  通过串联分子间C–N键和分子内CS键形成序列，开发了一种便捷高效的合成苯并[4,5]噻唑并[2,3- c ] [1,2,4]三唑的方法由邻-溴-芳基异硫氰酸酯和芳酰肼得到。以1 mol％CuCl 2 ·2H 2 O / 1 mol％1,10-菲咯啉提供了一系列优异的总收率的一系列苯并[4,5]噻唑并[2,3- c ] [1,2,4]三唑作为催化剂，水作为溶剂。
• Study of Oxidative Cyclization Using PhI(OAc)2 in the Formation of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles and Related Heterocycles – Scope and Limitations
  作者：Charles Demmer、Morten Jørgensen、Jan Kehler、Lennart Bunch

  DOI：10.1055/s-0033-1341159

  日期：——

  the synthesis of benzo[4,5]thiazolo[2,3- c ][1,2,4]triazoles and related heterocycles under mild conditions was herein developed. The key step of this transformation is an oxidative cyclization employing PhI(OAc) 2 as reagent. Scope and limitations (group functionality tolerance and sterics) were studied showing the robustness of the present methodology which can be used as potential access to new fused

  本文开发了一种在温和条件下合成苯并[4,5]噻唑并[2,3-c][1,2,4]三唑和相关杂环的一锅两步反应。这种转化的关键步骤是使用 PhI(OAc) 2 作为试剂的氧化环化。研究了范围和限制（基团功能耐受性和空间），显示了本方法的稳健性，可用作获取新的融合杂环库的潜在途径。
• Thallium(III) Salts Mediated Oxidative Cyclization of Arenecarbaldehyde Benzothiazol-2-ylhydrazones to Bridged Head Nitrogen Heterocycles
  作者：Om V. Singh、Varughese George

  DOI：10.1080/00397919408010575

  日期：1994.10

  arenecarbaldehydebenzothiazol-2-ylhydrazones (4) with thallium (III) acetate in refluxing acetic acid, thallium (III) acetate and thallium (III) nitrate in acetonitrile in presence of p-toluene sulphonic acid afforded 3-aryl-1,2,4-triazolo[3,4-b]benzothiazoles (6) by intramolecular cyclization in high yield. A mechanistic scheme for this transformation has been proposed.

  摘要 芳烃甲醛苯并噻唑-2-基腙 (4) 与乙酸铊 (III) 在回流乙酸中、乙酸铊 (III) 和硝酸铊 (III) 在乙腈中在对甲苯磺酸存在下氧化得到 3-芳基-1， 2,4-三唑并[3,4-b]苯并噻唑 (6) 通过分子内环化以高产率获得。已经提出了这种转变的机制方案。
• The Synthesis of Polyazaindenes and Related Compounds
  作者：G. A. REYNOLDS、J. A. VanALLAN

  DOI：10.1021/jo01092a023

  日期：1959.10
• Deshmukh; Patil; Jadhav, Indian Journal of Heterocyclic Chemistry, 2010, vol. 20, # 2, p. 163 - 166
  作者：Deshmukh、Patil、Jadhav、Shejwal

  DOI：——

  日期：——