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

页码：1398 / 1406

页数：9

共 89 条

[1] Synthesis of homochiral dihydroxy-4-nitroisoxazolines via one-pot asymmetric dihydroxylation - Reduction
Adamo, Mauro F. A.
Nagabelli, Murali
[J]. ORGANIC LETTERS, 2008, 10 (09) : 1807 - 1810
[2] Open analogues of arcyriaflavin A.: Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1,3-butadienes
Adeva, M
Sahagún, H
Caballero, E
de Clairac, RPL
Medarde, M
Tomé, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) : 3387 - 3394
[3] ALTUKHOV KV, 1976, USP KHIM+, V45, P2050
[4] KINETIC-STUDY OF THE HOMOLYTIC BROMINOLYSIS OF 1,2-DIARYLCYCLOPROPANES
APPLEQUIST, DE
GDANSKI, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) : 2502 - 2510
[5] Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents
Averina, Elena B.
Vasilenko, Dmitry A.
Gracheva, Yulia A.
Grishin, Yuri K.
Radchenko, Eugene V.
Burmistrov, Vladimir V.
Butov, Gennady M.
Neganova, Margarita E.
Serkova, Tatyana P.
Redkozubova, Olga M.
Shevtsova, Elena F.
Milaeva, Elena R.
Kuznetsova, Tamara S.
Zefirov, Nikolay S.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (04) : 712 - 720
[6] Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles
Averina, Elena B.
Vasilenko, Dmitry A.
Samoilichenko, Yuri V.
Grishin, Yuri K.
Rybakov, Victor B.
Kuznetsova, Tamara S.
Zefirov, Nikolay S.
[J]. SYNTHESIS-STUTTGART, 2014, 46 (08): : 1107 - 1113
[7] Heterocyclization of electrophilic alkenes with tetranitromethane revisited: regiochemistry and the mechanism of nitroisoxazole formation
Averina, Elena B.
Samoilichenko, Yuri V.
Volkova, Yulia A.
Grishin, Yuri K.
Rybakov, Victor B.
Kutateladze, Andrei G.
Elyashberg, Mikhail E.
Kuznetsova, Tamara S.
Zefirov, Nikolai S.
[J]. TETRAHEDRON LETTERS, 2012, 53 (12) : 1472 - 1475
[8] Medicinal Chemistry Perspective of Fused Isoxazole Derivatives
Barmade, Mahesh A.
Murumkar, Prashant R.
Sharma, Mayank Kumar
Yadav, Mange Ram
[J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (26) : 2863 - 2883
[9] Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles
Baschieri, Andrea
Bernardi, Luca
Ricci, Alfredo
Suresh, Surisetti
Adamo, Mauro F. A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) : 9342 - 9345
[10] Novel Colchicine-Site Binders with a Cyclohexanedione Scaffold Identified through a Ligand-Based Virtual Screening Approach
Canela, Maria-Dolores
Perez-Perez, Maria-Jesus
Noppen, Sam
Saez-Calvo, Gonzalo
Fernando Diaz, J.
Camarasa, Maria-Jose
Liekens, Sandra
Priego, Eva-Maria
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (10) : 3924 - 3938

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