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

共 39 条

[1] An unprecedented "Reverse" 1,2-migration of a nitro group within an α-aryl-β-nitroethenyl moiety driven by steric and stereoelectronic effects
Bianchi, Lara
Giorgi, Gianluca
Maccagno, Massimo
Petrillo, Giovanni
Rizzato, Egon
Spinelli, Domenico
Stenta, Marco
Tavani, Cinzia
LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (04) : 268 - 272
[2] 1,2-MIGRATION OF BENZYL GROUP IN INDOLES
TOKMAKOV, GP
GRANDBERG, II
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1994, (01): : 133 - 140
[3] 1,2-MIGRATION OF THE TRIMETHYLSILYL GROUP IN FREE-RADICALS
HARRIS, JM
MACINNES, I
WALTON, JC
MAILLARD, B
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 403 (03) : C25 - C28
[4] Studies on the heck reaction with alkenyl phosphates: Can the 1,2-migration be controlled? Scope and limitations
Ebran, Jean-Philippe
Hansen, Anders L.
Gogsig, Thomas M.
Skrydstrup, Troels
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) : 6931 - 6942
[5] 1,2-MIGRATION OF THE OH GROUP IN A STABLE BETA-HYDROXY SUBSTITUTED CARBOCATION
CHIKINEV, AV
SHAKIROV, MM
BUSHMELEV, VA
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1988, 37 (04): : 698 - 702
[6] Fluorodesilylations of fluorophenyltrimethylsilanes with elemental fluorine: discovery of a novel 1,2-migration of the trimethylsilyl group
Stuart, AM
Coe, PL
Moody, DJ
JOURNAL OF FLUORINE CHEMISTRY, 1998, 88 (02) : 179 - 184
[7] Gold(I)-Catalyzed 1,2-Migration of a SiMe3 Group on Naphthalene Rings
Yang, Qi
Liu, Liang
Zhang, Wen-Xiong
Xi, Zhenfeng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (01) : 272 - 276
[8] 1,2-MIGRATION OF METHYL-GROUP IN REACTION OF TERT-BUTYLETHYLENE WITH PHENYLSULFENYL FLUOBORATE
VOROBEVA, EA
KRIMER, MZ
SMIT, VA
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1974, 23 (11): : 2564 - 2564
[9] SYNTHESIS OF NONESTER PYRETHROIDS HAVING A 1-FLUORO-1-METHYLETHYL GROUP USING 1,2-MIGRATION OF AN ARYL GROUP
UNEME, H
OKADA, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (09) : 2401 - 2410
[10] HYDROGEN ABSTRACTION FROM SILYLAMINES - AN INVESTIGATION OF THE 1,2-MIGRATION OF THE TRIMETHYLSILYL GROUP IN AMINYL RADICALS
HARRIS, JM
WALTON, JC
MAILLARD, B
GRELIER, S
PICARD, JP
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (11): : 2119 - 2123

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