Uncommon 1,2-Migration of a Nitro Group Within a β-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details

被引：15

作者：

Bianchi, Lara ^{[1
]}

Ghelfi, Franco ^{[2
]}

Giorgi, Gianluca ^{[3
]}

Maccagno, Massimo ^{[1
]}

Petrillo, Giovanni ^{[1
]}

Spinelli, Domenico ^{[4
]}

Stenta, Marco ^{[5
]}

Tavani, Cinzia ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

[2] Univ Modena & Reggio Emilia, Dipartimento Chim, I-41100 Modena, Italy

[3] Univ Siena, Dipartimento Chim, I-53100 Siena, Italy

[4] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

[5] Ecole Polytech Fed Lausanne, Sch Life Sci, Lab Biomol Modeling, Inst Bioengin, CH-1015 Lausanne, Switzerland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 28期

关键词：

Synthetic methods; Heterocycles; Nitro group migration; Alkenes; TUMOR-CELL LINES; BUILDING-BLOCKS; NUCLEOPHILIC-SUBSTITUTION; BIOLOGICAL EVALUATION; ISOXAZOLES; 3,4-DINITROTHIOPHENE; ISOMERIZATION; EXPLOITATION; ACCESS; OXIDE;

D O I：

10.1002/ejoc.201300856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unusual migration of a nitro group from the - to the -position of a -aryl--nitroethenyl moiety, following a nitrocyclopropane to isoxazoline N-oxide isomerization, has been studied from a mechanistic and synthetic points of view. As a result, two series of isomeric isoxazoline N-oxides could be obtained under controlled conditions. When reacted with diazomethane, a model transposed isoxazoline cleanly furnished a new, interesting pyrazolylisoxazole.

引用

页码：6298 / 6309

页数：12

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