Ag2O/PPh3/TBD催化合成3,6-二氮杂二环[3.2.1]辛烷衍生物
Ag2O/PPh3/TBD-Catalyzed the Synthesis of 3,6-Diazabicyclo[3.2.1]octane Derivatives
侯良宁 1钟玮 1张凯强 1王宁 1周鸿池 1王海飞1
作者信息
- 1. 湖南工业大学 生命科学与化学学院,湖南 株洲 412007
- 折叠
摘要
五元含氮杂环是吲哚生物碱和药物中间体分子中的一个重要的结构单元,在过去几十年中,单环的吡咯烷的合成已有大量的文献报道,其中甲亚胺叶立德与缺电子烯烃之间的1,3-偶极环加成是最常用的制备丰富多样吡咯烷的方法,但带有吡咯烷结构的二环化合物的合成却少有报道.本文以不同系列的偶氮甲碱叶立德与a-取代的末端烯烃酰胺为原料,Ag(Ⅰ)/PPh3为催化体系,在有机或无机碱的作用下,一步实现了消旋体3,6-二氮杂二环[3.2.1]辛烷衍生物的合成.与现有方法相比,本实验方法步骤简单,原料廉价易得,反应条件温和,底物适应性广.
Abstract
The five membered nitrogen-containing heterocycle is an important structural unit in indole alkaloids and drug intermediates.In the past few decades,there have been numerous literature reports on the synthesis of single cyclic pyrrolidone.Among them,the 1,3-dipolar cycloaddition between imine ylides and electron-deficient olefins is the most commonly used method for preparing a wide variety of pyrrolidines.However,there are few reports on the synthesis of bicyclic compounds with pyrrolidine structures.This article reports the one-step synthesis of racemic 3,6-diazabicyclo[3.2.1]octane derivatives using different series of azomethine ylides and α-substituted terminal olefin amides as raw materials,and Ag(I)/PPh3 as catalytic system under the action of organic or inorganic bases.Compared with existing methods,this experimental method has the characteristics of simple steps,inexpensive and easily obtainable raw materials,mild reaction conditions,and wide substrate adaptability.
关键词
氧化银/吡咯烷/[3+2]环加成/偶氮甲碱叶立德/3,6-二氮杂二环[3.2.1]辛烷Key words
silver oxide/pyrrolidines/[3+2]cycloaddition/azomethine ylides/3,6-diazabicyclo[3.2.1]octanes引用本文复制引用
基金项目
湖南省自然科学基金(2021JJ50005)
湖南省自然科学基金(2023JJ60446)
出版年
2024
NETL
NSTL
万方数据