摘要
α-氨基酮类化合物是重要的药物分子和高活性的反应中间体。以2-苯乙炔基苯甲醛、N-苯甲酰基亚胺前体为原料,噻唑衍生的氮杂环卡宾催化发生氮杂安息香反应,以56~91%的产率合成了8个不同取代的2-苯甲酰胺基-2-苯基-1-(2'-苯乙炔基)苯基乙-1-酮4。采用1HNMR、13CNMR、HRMS对产物4进行结构鉴定。为了验证反应的实用性,对4g的合成进行了放大实验,产率85%。此反应具有条件温和、底物适应范围较广、步骤简单、产率高等特点,可为工业化应用提供一定参考价值。
α-Amino ketones are important pharmaceutical molecules and highly active reaction intermediates.Using 2-(phenylethynyl)benzaldehyde and N-benzoyl imine precursor as starting materials,an aza-benzoin condensation catalyzed by a thiazole-derived N-heterocyclic carbene was conducted,synthesizing eight differently substituted 2-benzamido-2-phenyl-1-(2'-phenylethynyl)phenyl ethan-1-one 4 with yields ranging from 56%to 91%.The structure of product 4 was identified by~1H NMR,^(13)C NMR and HRMS.To verify the practicality of the reaction,a scale-up experiment was performed for the synthesis of 4g,yielding 85%.This reaction was characterized by mild conditions,a broad substrate scope,simple procedures,and high yields,providing a valuable reference for industrial applications.
作者
张飞
丁雅丽
张华山
ZHANG Fei;DING Ya-li;ZHANG Hua-shan(College of Pharmacy,Qinghai Minzu University,Xining 810007,China;College of Chemistry and Materials Science,Qinghai Minzu University,Xining 810007,China)
出处
《化学研究与应用》
北大核心
2025年第1期224-229,共6页
Chemical Research and Application
基金
青海民族大学高层次人才项目(2022GCC08,2021XJG16)资助
青海民族大学大学生创新创业训练计划项目(2024-DCXM-64)资助。
关键词
氮杂安息香反应
α-氨基酮
噻唑衍生的氮杂环卡宾
催化
aza-benzoin condensation
α-amino ketone
thiazole-derived N-heterocyclic carbene
catalysis
