4,6,7-trimethoxyquinazoline-2-carbonitrile | 182620-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4,6,7-trimethoxyquinazoline-2-carbonitrile
• 英文别名: 4,6,7-Trimethoxy-2-quinazolinecarbonitrile
• CAS: 182620-34-4
• 化学式: C₁₂H₁₁N₃O₃
• 分子量: 245.238
• InChiKey: QVVUZHVZVVHOHI-UHFFFAOYSA-N

物化性质

• 沸点：
  437.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯腈 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 4,6,7-trimethoxyquinazoline-2-carbonitrile
  参考文献：
  名称：

  Antimicrobial evaluation of 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones, 4-alkoxyquinazolin-2-carbonitriles and N-arylimino-1,2,3-dithiazoles

  摘要：

  Novel 3,1-benzoxazinones, 3,1-benzothiazinones and 4-alkoxyquinazolines have been synthesized via N-aryl-1,2,3-dithiazoles derivatives. The antibacterial and antifungal activity of these compounds were measured; the dithiazoles are significantly active against fungi. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00423-4

文献信息

• The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2-carbonitriles using triphenylphosphine
  作者：Panayiotis A. Koutentis、Sophia S. Michaelidou

  DOI：10.1016/j.tet.2010.06.020

  日期：2010.8

  react with triphenylphosphine and p-toluenesulfonic acid in MeOH to give 3-aminoindole-2-carbonitriles 2b–f in 63–75% yields. Under analogous conditions 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 2g gives only 4,5-dimethoxyanthranilonitrile 8g and 4,6,7-trimethoxyquinazoline-2-carbonitrile 14g, but in refluxing dry PhMe in the absence of p-toluenesulfonic acid 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide

  2-氰基cyanothioformanilide 3A与在水的存在下发生反应的三苯基膦，得到2-（氰基亚甲基氨基）苄腈4a中，2-（cyanomethylamino）苄腈5，3-氨基吲哚-2-甲腈2A和（2-氰基吲哚-3-基）iminotriphenylphosphorane 6a。在对甲苯磺酸在MeOH中的存在下，2-氰基氰基硫代甲酰甲酰胺3a与三苯基膦（2当量）之间的反应以90％的产率得到3-氨基吲哚-2-腈2a。在相同条件下，2-（氰基亚甲基氨基）苄腈4a得到蒽腈8a，3-氨基吲哚-2-腈2a和N-（2-氰基苯基）甲酰胺9。此外，取代的2-氰基氰基硫代甲酰胺基化物3b - f与三苯基膦和对甲苯磺酸在MeOH中反应，以63-75％的收率得到3-氨基吲哚-2-腈2b - f。在类似条件下，2-氰基-4,5-二甲氧基苯基氰基硫代甲酰苯胺2g仅产生4,5-二甲氧基蒽腈8g和4,6,7-三甲氧
• New route to 4-alkoxyquinazoline-2-carbonitriles
  作者：Thierry Besson、Charles W. Rees

  DOI：10.1039/p19960002857

  日期：——

  A new, direct synthesis is described for the relatively rare but synthetically very versatile quinazoline-2-carbonitriles from antranilonitriles and 4,5-dichloro-1,2,3-dithiazolium chloride 1. Treatment of iminodithiazole 6, from 4,5-dimethoxyanthranilonitrile and the salt 1, with alcohols and a base gives 4-alkoxyquinazoline-2-carbonitriles 8 in good yield. Treatment of the parent iminodithiazole

  描述了一种新的直接合成方法，该方法可从苯甲腈和4,5-二氯-1,2,3-二噻唑鎓1中相对稀少但合成用途非常广泛的喹唑啉-2-腈进行处理。由4,5-二甲氧基蒽腈处理亚氨基二噻唑6，盐1与醇和碱一起以良好的收率得到4-烷氧基喹唑啉-2-腈8。用醇和氢化钠处理母体亚氨基二噻唑2（R ＝ H； X ＝ CN）得到较低产率的类似喹唑啉12，尽管这些产率大大提高并且在微波辐射下缩短了反应时间。或者，可以将亚胺6转化为更具反应性的氰基硫代甲酰胺7，其在醇中短暂加热后，以高收率得到相同的喹唑啉8。
• Expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles using microwave irradiation
  作者：Thierry Besson、Marie-Joëlle Dozias、Jérôme Guillard、Patrick Jacquault、Marie-Dominique Legoy、Charles W. Rees

  DOI：10.1016/s0040-4020(98)00276-2

  日期：1998.6

  Conversion of N-arylimino-4-chloro-5H-1,2,3-dithiazole 11 into the 4-alkoxyquinazoline-2-carbonitriles 13a-i and of the aryl isothiocyanates 15 into aryl thiocarbamates 16a-j with sodium alkoxides in the corresponding alcohol, either by conventional thermolysis or by microwave irradiation are described and directly compared. Microwave irradiation of the solutions in open vessels in a monomode system with focused irradiation and continuous temperature control (Synthewave S402 reactor) usually gave cleaner, faster and higher yielding reactions. These reactions could be safely and beneficially scaled up to multigram quantities in a larger reactor (Synthewave S1000). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Antimicrobial evaluation of 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones, 4-alkoxyquinazolin-2-carbonitriles and N-arylimino-1,2,3-dithiazoles
  作者：Thierry Besson、Charles W. Rees、Gilles Cottenceau、Anne-Marie Pons

  DOI：10.1016/0960-894x(96)00423-4

  日期：1996.10

  Novel 3,1-benzoxazinones, 3,1-benzothiazinones and 4-alkoxyquinazolines have been synthesized via N-aryl-1,2,3-dithiazoles derivatives. The antibacterial and antifungal activity of these compounds were measured; the dithiazoles are significantly active against fungi. Copyright (C) 1996 Elsevier Science Ltd