TBAI-促进3-氧-3-芳基丙腈与芳基磺酰肼的三组分反应  

TBAI-promoted three-componentreactions of 3-oxo-3-arylpropanenitriles with arylsulfonylhydrazides

作　　者：李雪 韦玥婷 刘平[1] 顾承志[1] 何林[1] LI Xue;WEI Yueting;LIU Ping;GU Chengzhi;HE Lin(School of Chemistry and Chemical Engineering/Key Laboratory for Green Process of Chemical Engineering of Xinjiang Bingtuan,Shihezi University,Shihezi,Xinjiang 832003,China)

机构地区：[1]石河子大学化学化工学院/化工绿色过程兵团重点实验室,新疆石河子832003

出　　处：《石河子大学学报（自然科学版）》2022年第3期272-277,共6页Journal of Shihezi University(Natural Science)

基　　金：国家自然科学基金(21563025)。

摘　　要：吡唑-5-胺是一类重要的五元杂环化合物,具有多种药理和生物活性,对于吡唑-5-胺的合成和衍生化在有机合成领域具有重要意义。本文建立了3-氧代-3-芳基丙腈与芳基磺酰肼的新的三组分反应,在四丁基碘化铵(TBAI)的作用下,依次通过环化、芳硫化反应实现了3-芳基-4-(芳硫基)-1H-吡唑-5-胺骨架的构建,最佳反应条件为:3-氧代-3-芳基丙腈(0.3 mmol),芳基磺酰肼(0.9 mmol),TBAI (0.5 equiv.),EtOH (0.5 mL),反应温度80℃,反应时间6 h。该体系具有反应条件温和,底物适用范围广,原料廉价易得等优点。Pyrazol-5-amines as an important class of five-membered heterocycles have exhibited a variety of pharmacological and biological activities.Therefore, it is of great significance for the synthesis and derivatization of pyrazol-5-amine in the field of organic synthesis.In this paper, new three-component reactions of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides have been established, and an expanded inventory of 3-aryl-4-(arylthio)-1H-pyrazol-5-amines is synthesized by sequential cyclization and sulfenylation reactions under the action of TBAI.The optimal reaction conditions were as follow: 3-oxo-3-arylpropanenitrile(0.3 mmol),arylsulfonyl hydrazide(0.9 mmol),TBAI(0.5 equiv.),EtOH(0.5 mL),reaction temperature 80℃,reaction time 6 h.The protocol represents broad substrate scope, good functional group tolerance, and mild reaction conditions.

关 键 词：三组分反应 3-氧-3-芳基丙腈 芳基磺酰肼 芳基硫醚 氨基吡唑 

分 类 号：O625.13[理学—有机化学]