1-(2,3-dihydro-1H-pyrido<3,2,1-kl>phenothiazin-3-yl)-2-pyrrolidinone

• 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-(2,3-dihydro-1H-pyrido<3,2,1-kl>phenothiazin-3-yl)-2-pyrrolidinone
• 英文别名: 3-(2-Pyrrolidinon-1-yl)-1,2,3,11b-tetrahydrobenzo<1,10>phenothiazine；1-(8-Thia-1-azatetracyclo[7.7.1.02,7.013,17]heptadeca-2,4,6,9,11,13(17)-hexaen-14-yl)pyrrolidin-2-one
• 化学式: C₁₉H₁₈N₂OS
• 分子量: 322.431
• InChiKey: JWZSTBWNAKNZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,3-dihydro-1H-pyrido<3,2,1-kl>phenothiazin-3-yl)-2-pyrrolidinone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到3-(2-Pyrrolidin-1-yl)-1,2,3,11b-tetrahydrobenzo<1,10>phenothiazine
  参考文献：
  名称：

  Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines

  摘要：

  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.

  DOI：

  10.1021/jo00118a014
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 1-<(1,4-phenothiazin-10-yl)methyl>benzotriazole 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以71%的产率得到1-(2,3-dihydro-1H-pyrido<3,2,1-kl>phenothiazin-3-yl)-2-pyrrolidinone
  参考文献：
  名称：

  四环五环和吩噻嗪的合成通过苯并三唑方法

  摘要：

  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。

  DOI：

  10.1002/jhet.5570360223

文献信息

• 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.
• 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。