6H-pyrido[1,2-a]quinazoline | 23992-66-7

• 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: 6H-pyrido[1,2-a]quinazoline
• 英文别名: 6h Pyrido[1,2 a]quinazolin
• CAS: 23992-66-7
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: RBBCITXBUXOTTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(2-iodobenzyl)pyridin-2-amine 在 potassium tert-butylate 作用下， 以 氨 为溶剂， 反应 3.0h， 以61%的产率得到6H-pyrido[1,2-a]quinazoline
  参考文献：
  名称：

  Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(ortho-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis

  摘要：

  The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.

  DOI：

  10.1021/jo9025918

文献信息

• SUBSTITUIERTE 3,4-DIHYDRO-PYRIDO[1,2-A]PYRIMIDINE
  申请人：Grünenthal GmbH

  公开号：EP1326866A1

  公开（公告）日：2003-07-16
• US7230103B2
  申请人：——

  公开号：US7230103B2

  公开（公告）日：2007-06-12
• [DE] SUBSTITUIERTE 3,4-DIHYDRO-PYRIDO[1,2-A]PYRIMIDINE<br/>[EN] SUBSTITUTED 3.4-DIHYDRO-PYRIDO[1,2-A]PYRIMIDINES<br/>[FR] 3,4-DIHYDRO-PYRIDO[1,2-A]PYRIMIDINES SUBSTITUEES
  申请人：GRUENENTHAL GMBH

  公开号：WO2002030933A1

  公开（公告）日：2002-04-18

  Die Anmeldung betrifft substituierte 3,4-Dihydro-pyrido[1,2-a]pyrimidine der allgemeinen Struktur (I), Verfahren zu ihrer Herstellung, sie enthaltende Substanzbibliotheken, Arzneimittel, die diese Verbindungen enthalten, die Verwendung dieser Verbindungen zur Herstellung von Arzneimitteln zur Behandlung von Schmerz, Harninkontinenz, Juckreiz, Tinnitus aurium und/oder Diarrhoe sowie diese Verbindungen enthaltende pharmazeutische Zusammensetzungen.
• Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from <i>N</i>-(<i>ortho</i>-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis
  作者：María E. Budén、Viviana B. Dorn、Martina Gamba、Adriana B. Pierini、Roberto A. Rossi

  DOI：10.1021/jo9025918

  日期：2010.4.2

  The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.