文献类型：期刊文献

中文题名：吡咯烷-2-酮化合物的合成

英文题名：Synthesis of Pyrrolidine-2-ones

作者：李金辉[1];赵敏[1];陈建中[2]

机构：[1]华东理工大学化学与分子工程学院,上海200237;[2]上海交通大学化学化工学院,上海200240

年份：2023

卷号：45

期号：10

起止页码：138

中文期刊名：化学试剂

外文期刊名：Chemical Reagents

收录：CSTPCD;;北大核心:【北大核心2020】；

基金：国家自然科学基金项目(21702134)。

语种：中文

中文关键词：吡咯烷-2-酮;芳基烷基酮;芳基烷基酮肟;N-(二苯基膦酰基)-亚胺;伯胺

外文关键词：pyrrolidin-2-one;aryl alkyl ketone;aryl alkyl ketone oxime;N-(diphenylphosphine)-imine;primary amines

摘要：以常见的苯乙酮为起始原料,通过盐酸羟胺的加成形成肟,部分肟在钯碳/氢气的条件下直接还原以较好产率得到相应伯胺;另一部分难以直接还原的肟,通过二苯基氯化膦的修饰,随后用硼氢化钠还原、氯化氢脱保护可得到一系列相应的伯胺。最后伯胺在碱性条件下与4-氯丁酰氯进行环化反应,以良好产率得到广泛用于生物活性物质的N-(1′-芳基烷基)-2-吡咯烷酮化合物。目标产物结构通过1HNMR、13 CNMR、HRMS-ESI等方式表征。
N-(diphenylphosphinyl)-imines were prepared via the reaction of aryl acetophenone with hydroxylamine hydrochloride.Among them,some primary amines were obtained by directly reducing the corresponding oximes under Pd/C/H 2 conditions.Regarding the oximes that are difficult to be directly reduced,they were modified with diphenyl phosphorus chloride,reduced with sodium borohydride,and deprotected with hydrogen chloride to obtain primary amines.The desired products,which can be used in the synthesis of many bioactive compounds,were obtained by cyclization of a primary amine with 4-chlorobutyryl chloride under basic conditions.The structures of the target products were characterized by 1HNMR,13 CNMR,and HRMS-ESI.