Preparation and reactivity of [2-(3-methyl-4-nitro-isoxazol-5-yl)-vinyl]-amines

被引:3
作者
Dere, Ravindra [1 ]
Monasterolo, Claudio [1 ]
Moccia, Maria [1 ]
Adamo, Mauro F. A. [1 ]
机构
[1] Royal Coll Surgeons Ireland, Dept Pharmaceut & Med Chem, CSCB, Dublin 2, Ireland
关键词
Polyfunctional scaffolds; 4-Nitroisoxazoles; Isoxazoles; Enamines; BETA-ENAMINO ESTERS; MULTICOMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; AZA-ANNULATION; ROUTE; ALPHA; REDUCTION; AMINO;
D O I
10.1016/j.tetlet.2015.11.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report our investigation into the reactivity of 5-enamino-4-nitroisoxazoles. This study revealed that the title compounds, in spite of conjugation to the 4-nitroisoxazole, displayed similar reactivity to enamines, reacting with electrophiles to form new C-C, C-N, and C-Cl bonds. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7168 / 7171
页数:4
相关论文
共 44 条
[1]   Modular syntheses of isoxazoloazepinones and pyrazoloazepinones [J].
Adamo, Mauro F. A. ;
Duffy, Eleanor F. ;
Donati, Donato ;
Sarti-Fantoni, Piero .
TETRAHEDRON, 2007, 63 (12) :2684-2688
[2]   Multicomponent synthesis of 3-indolepropionic acids [J].
Adamo, Mauro F. A. ;
Konda, Vivekananda R. .
ORGANIC LETTERS, 2007, 9 (02) :303-305
[3]  
Adamo MFA, 2007, HETEROCYCLES, V71, P1173
[4]   Modular synthesis of isoxazolopyridones and pyrazolopyridones [J].
Adamo, Mauro F. A. ;
Duffy, Eleanor F. ;
Donati, Donato ;
Sarti-Fantoni, Piero .
TETRAHEDRON, 2007, 63 (09) :2047-2052
[5]   Multicomponent synthesis of 3-heteroarylpropionic acids [J].
Adamo, Mauro F. A. ;
Duffy, Eleanor F. .
ORGANIC LETTERS, 2006, 8 (22) :5157-5159
[6]   Preparation of mono-labelled aliphatic polyacids via isoxazole derivatives [J].
Adamo, Mauro F. A. ;
Sarti-Fantoni, Piero ;
Chimichi, Stefano ;
Sandrelli, Alessandro .
TETRAHEDRON LETTERS, 2010, 51 (48) :6310-6312
[7]   Reaction of 5-(1-bromo-2-aryl-vinyl)-3-methyl-4-nitro-isoxazoles and 1,3-dicarbonyl compounds [J].
Adamo, Mauro F. A. ;
Suresh, Surisetti ;
Piras, Linda .
TETRAHEDRON, 2009, 65 (27) :5402-5408
[8]   Multicomponent synthesis of spiroisoxazolines [J].
Adamo, MFA ;
Donati, D ;
Duffy, EF ;
Sarti-Fantoni, P .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8395-8399
[9]   The reactivity of 3-methyl-4-nitro-5-styrylisoxazole with some bis-enolisable ketones [J].
Adamo, MFA ;
Chimichi, S ;
De Sio, F ;
Donati, D ;
Sarti-Fantoni, P .
TETRAHEDRON LETTERS, 2002, 43 (23) :4157-4160
[10]  
Alan C., 2003, ORG BIOMOL CHEM, V2, P1638