Synthesis of 4-Nitroisoxazoles via NO/NO2-Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones

被引：7
作者：
Vasilenko, Dmitry A. [1 ]
Sadovnikov, Kirill S. [1 ]
Sedenkova, Kseniya N. [1 ,2 ]
Kurova, Anastasiya V. [1 ]
Grishin, Yuri K. [1 ]
Kuznetsova, Tamara S. [1 ]
Rybakov, Victor B. [1 ]
Volkova, Yulia A. [1 ,3 ]
Averina, Elena B. [1 ,2 ]
机构：
[1] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1 Bd 3, Moscow 119991, Russia
[2] Inst Physiologically Act Cpds, Severny Proezd 1, Chernogolovka 142432, Moscow Region, Russia
[3] RAS, ND Zelinsky Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia
来源：
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 09期
基金：
俄罗斯科学基金会;
关键词：
4-nitroisoxazoles; alkenes; ketones; heterocycles; ring closure-tert-butyl nitrite; heterocyclization; tetranitromethane; ASYMMETRIC CONJUGATE ADDITION; VINYLOGOUS MICHAEL ADDITION; 1,3-DIPOLAR CYCLOADDITION; ELECTROPHILIC ALKENES; DERIVATIVES; TETRANITROMETHANE; CHEMISTRY; CONSTRUCTION; PHARMACOLOGY; INHIBITORS;
D O I：
10.1055/s-0039-1690053
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward approach for the synthesis of 4-nitroisoxazoles has been developed via heterocyclization of aryl/hetaryl-substituted alpha,beta-unsaturated ketones upon treatment with tetranitromethane-triethylamine (TNM-TEA) complex or t-BuONO. This strategy features high efficiency and wide substrate tolerance under simple reaction conditions.
引用
收藏
页码：1398 / 1406
页数：9
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