1-<(1,4-phenothiazin-10-yl)methyl>benzotriazole | 149222-04-8

• 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: 1-<(1,4-phenothiazin-10-yl)methyl>benzotriazole
• 英文别名: 10-(benzotriazol-1-yl)methylphenothiazine；10-(Benzotriazol-1-ylmethyl)phenothiazine
• CAS: 149222-04-8
• 化学式: C₁₉H₁₄N₄S
• 分子量: 330.413
• InChiKey: NRTUMDOXVOHTSS-UHFFFAOYSA-N

物化性质

• 沸点：
  546.6±39.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 1-<(1,4-phenothiazin-10-yl)methyl>benzotriazole 在 lithium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到9-methyl-9-(1-methylethenyl)-9,10,11,12-tetrahydropyrido<3,2,1-kl>-1,4-phenothiazine
  参考文献：
  名称：

  Lithium tetrafluoroborate-assisted reactions of N-(.alpha.-aminoalkyl)benzotriazoles with olefins and 1,3-dienes. New syntheses of 1,2,5,6-tetrahydropyridinium salts, 1,2,3,4-tetrahydroquinolines, and some related heterocyclic systems

  摘要：

  Lithium tetrafluoroborate efficiently assists the ionization of N-(alpha-aminoalkyl)benzotriazoles in tetrahydrofuran solution to generate reactive iminium intermediates, which can be trapped with electron-rich olefins and with 1,3-dienes. Hetero Diels-Alder cycloadditions of N-(alpha-dialkylami-noalkyl)benzotriazoles and lithium tetrafluoroborate with 1,3-dienes thus gave 1,2,5,6-tetrahydropyridinium salts, while reactions of N-[alpha-(arylamino)alkyl]benzotriazoles with olefins and 1,3-dienes afforded substituted 1,2,3,4-tetrahydroquinolines, as well as examples of the new heterocyclic systems indeno[2,1-c]quinoline and pyrido[3,2,1-kl]-1,4-phenothiazine.

  DOI：

  10.1021/jo00067a043
• 作为产物：
  描述：

  1H-苯并三唑-1-甲醇 、 吩噻嗪 以 甲苯 为溶剂， 反应 30.0h， 以65%的产率得到1-<(1,4-phenothiazin-10-yl)methyl>benzotriazole
  参考文献：
  名称：

  Lithium tetrafluoroborate-assisted reactions of N-(.alpha.-aminoalkyl)benzotriazoles with olefins and 1,3-dienes. New syntheses of 1,2,5,6-tetrahydropyridinium salts, 1,2,3,4-tetrahydroquinolines, and some related heterocyclic systems

  摘要：

  Lithium tetrafluoroborate efficiently assists the ionization of N-(alpha-aminoalkyl)benzotriazoles in tetrahydrofuran solution to generate reactive iminium intermediates, which can be trapped with electron-rich olefins and with 1,3-dienes. Hetero Diels-Alder cycloadditions of N-(alpha-dialkylami-noalkyl)benzotriazoles and lithium tetrafluoroborate with 1,3-dienes thus gave 1,2,5,6-tetrahydropyridinium salts, while reactions of N-[alpha-(arylamino)alkyl]benzotriazoles with olefins and 1,3-dienes afforded substituted 1,2,3,4-tetrahydroquinolines, as well as examples of the new heterocyclic systems indeno[2,1-c]quinoline and pyrido[3,2,1-kl]-1,4-phenothiazine.

  DOI：

  10.1021/jo00067a043

文献信息

• Reactions of<i>N</i>-aryl-1<i>H</i>-benzotriazolyl-1-methanamines with allyl trimethylsilanes. A facile route to trialkylsilane tetrahydroquinolines
  作者：Alan R. Katritzky、Xilin Cui、Qiuhe Long

  DOI：10.1002/jhet.5570360207

  日期：1999.3

  N-Aryl-1H-benzotriazolyl-1-methanamines 1, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo Lewis acid assisted reactions with allyl trimethylsilanes to give 4-(trimethylsilyl)methyl-1,2,3,4-tetrahydroquinolines 2 in good to high yields.

  N-芳基-1 H-苯并三唑基-1-甲胺1易于从苯胺与甲醛和苯并三唑的缩合反应中进行，与路易斯烯酸三甲基硅烷进行路易斯酸辅助反应，得到4-（三甲基甲硅烷基）甲基-1,2,3,4 -四氢喹啉2高至高收率。
• Synthesis of tetracyclic and pentacyclic phenothiazines<i>via</i>benzotriazole methodology
  作者：Alan R. Katritzky、Samia Agamy、Baozhen Yang、Guofang Qiu

  DOI：10.1002/jhet.5570360223

  日期：1999.3

  Treatment of 10-(benzotriazol-1-yl)alkylphenothiazine with electron-rich alkenes in the presence of zinc bromide gave tetracyclic phenothiazines 4 and 9 as well as pentacyclic phenothiazines 5, which have potential use in the pharmaceutical industry.

  在溴化锌存在下用富电子烯烃处理10-（苯并三唑-1-基）烷基吩噻嗪产生了四环吩噻嗪4和9以及五环吩噻嗪5，它们在制药工业中具有潜在的用途。
• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with .alpha.,.beta.-Unsaturated Ethers. A Novel Route to 1,4- and 1,3-Disubstituted 1,2,3,4-Tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00113a043

  日期：1995.4

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 3, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo acid-catalyzed reactions with ethyl vinyl ether to give 1-allkyl-4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 10 and their benzotriazol-2-yl isomers 11. The reaction mechanism involves formation of 1-alkyl-4-ethoxy-1,2,3,4-tetrahydroquinolines 8 as isolable intermediates, followed by substitution of the ethoxy group in 8 with benzotriazole to produce 10 and 11, Treatment with Grignard reagents in toluene converts compounds 10 and 11 in good yield to 4-alkyl- or 4-aryltetrahydroquinolines 12. 2,3-Dihydrofuran and 3,4-dihydro-2H-pyran undergo similar reaction sequences giving tetrahydroquinolines additionally substituted by 3-(beta-hydroxyethyl) and 3-(gamma-hydroxypropyl) groups, respectively. The stereochemistry of 1,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines is assigned on the basis of NOE methodology. An unusual reduction of the benzotriazolyl moiety to a phenylamino group is observed in the case of product 43 obtained from the reaction of 10-(benzotriazol-1-ylmethyl)-4H-phenothiazine with ethyl vinyl ether.
• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00118a014

  日期：1995.6

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.
• US7635181B2
  申请人：——

  公开号：US7635181B2

  公开（公告）日：2009-12-22