乙腈与吡咯苯胺构筑喹喔啉的[5+1]环化反应
Acetonitrile and Pyrrolidine Construct[5+1]Cyclization Reaction of Quinoxaline
万佳 1李珍珍 1刘珊珊1
作者信息
- 1. 陕西科技大学 化学与化工学院,陕西 西安 710021
- 折叠
摘要
开发了一种乙腈参与的[5+1]环化反应合成喹喔啉衍生物,该方法以吡咯苯胺为底物,乙腈既为溶剂,又可以作为反应试剂参与反应,在无外加金属催化剂的条件下,实现[5+1]环化高效构建吡咯并[1,2-a]喹喔啉分子.经过一系列条件筛选之后得到最佳反应条件为:对甲基苯磺酸一水合物(3 eq)为催化剂,H2O(5 eq),乙腈为溶剂(0.5 mL),于 140℃条件下反应 14 小时,产率最高达到 85%.除吡咯苯胺外,还成功兼容了一系列不同的导向基团,该反应可应用于较多的底物范围.
Abstract
A[5+1]cyclization reaction involving acetonitrile was developed to synthesize quinoxaline derivatives.Using pyrrolidine as substrate and acetonitrile as both solvent and reagent,the[5+1]cyclization of pyrrolidine[1,2-a]quinoxaline molecules was achieved without additional metal catalyst.After a series of screening conditions,the optimal reaction conditions were as follows:p-methylbenzenesulfonic acid monohydrate(3 eq)as catalyst,H2O(5 eq),acetonitrile as solvent(0.5 mL),reaction at 140℃for 14 hours,the highest yield of 85%.In addition to pyrrolidine,a series of different guiding groups are successfully compatible,and the reaction can be applied to a wide range of substrates.
关键词
喹喔啉骨架/乙腈/吡咯苯胺/酸催化/[5+1]环化Key words
quinoxaline skeleton/acetonitrile/pyrrolidine/acid catalysis/[5+1]cyclization引用本文复制引用
出版年
2024
国家科技期刊平台
NSTL
万方数据