Reaction between isocyanides and nitrostyrenes in water: a novel and efficient synthesis of 5-(alkylamino)-4-aryl-3-isoxazolecarboxamides

被引:27
作者
Adib, Mehdi [1 ]
Mahdavi, Mohammad [1 ]
Ansari, Samira [1 ]
Malihi, Farzad [1 ]
Zhu, Long-Guan [2 ]
Bijanzadeh, Hamid Reza [3 ]
机构
[1] Univ Tehran, Sch Chem, Univ Coll Sci, Tehran, Iran
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
[3] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
关键词
5-(Alkylamino)-4-aryl-3-isoxazolecarboxamides; Isocyanides; Nitrostyrenes; Three-component reactions; Synthesis in water; ONE-POT SYNTHESIS; 3-COMPONENT SYNTHESIS; MULTICOMPONENT REACTIONS; MICROWAVE IRRADIATION; CONVENIENT SYNTHESIS; ORGANIC-REACTIONS; ISOXAZOLES; PYRROLES; DISCOVERY;
D O I
10.1016/j.tetlet.2009.09.069
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
A novel synthesis of 5-(alkylamino)-4-aryl-3-isoxazolecarboxamides is described. Heating a mixture of an isocyanide and a nitrostyrene in water afforded the title compounds in excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7246 / 7248
页数:3
相关论文
共 49 条
[1]
A new, one-pot, multi-component synthesis of imines of 3-amino-2-arylimidazo[1,2-a]pyridines, 3-amino-2-arylimidazo[1,2-a]pyrazines, and 3-amino-2-arylimidazo[1,2-a]pyrimidines [J].
Abid, Mehdi ;
Sheibani, Esmail ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2008, 64 (47) :10681-10686
[2]
Efficient highly diastereoselective synthesis of 1,8a-dihydro-7H-imidazo[2,1-b][1,3]oxazines [J].
Adib, M ;
Sheibani, E ;
Mostofi, M ;
Ghanbary, K ;
Bijanzadeh, HR .
TETRAHEDRON, 2006, 62 (14) :3435-3438
[3]
A Novel, One-Pot, Efficient Synthesis of 2-Aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones [J].
Adib, Mehdi ;
Sayahi, Mohammad Hosein ;
Ziyadi, Hakimeh ;
Zhu, Long-Guan ;
Bijanzadeh, Hamid Reza .
SYNTHESIS-STUTTGART, 2008, (20) :3289-3294
[4]
A novel and simple synthesis of 9H-Pyrimido[4,5-b]indoles under microwave irradiation and solvent-free conditions [J].
Adib, Mehdi ;
Mohammadi, Bagher ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2008, (02) :177-180
[5]
A new, one-pot, three-component synthesis of 4H-pyrido[1,2-a]-pyrimidines, 4H-pyrimido[1,2-a]pyrimidines, and 4H-pyrazino[ 1,2-a] pyrimidines [J].
Adib, Mehdi ;
Sayahi, Mohammad Hosein ;
Ziyadi, Hakimeh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2007, 63 (45) :11135-11140
[6]
A novel, one-pot and three-component synthesis of α-quinoxalinyl triphenylphosphoranes [J].
Adib, Mehdi ;
Sheibani, Esmaeil ;
Abbasi, Alireza ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2007, 48 (07) :1179-1182
[7]
One-pot three-component synthesis of 3-Amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines [J].
Adib, Mehdi ;
Koloogani, Somayeh Aali ;
Abbasi, Alireza ;
Bijanzadeh, Hamid Reza .
SYNTHESIS-STUTTGART, 2007, (19) :3056-3060
[8]
A novel, one-pot, three-component synthesis of 1,2,4-oxadiazoles under microwave irradiation and solvent-free conditions [J].
Adib, Mehdi ;
Mahdavi, Mohammad ;
Mahmoodi, Niusha ;
Pirelahi, Hooshang ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2006, (11) :1765-1767
[9]
Efficient Synthesis of Imidazo[2,1-b] [1,3]benzothiazoles and 9H-Imidazo[1,2-a][1,3]benzimidazoles under Solvent-Free Conditions [J].
Adib, Mehdi ;
Sheibani, Esmail ;
Zhu, Long-Guan ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2008, (19) :2941-2944
[10]
A Novel One-Pot, Three-Component Synthesis of Dialkyl 5-(Alkylamino)-1-aryl-1H-pyrazole-3,4-dicarboxylates [J].
Adib, Mehdi ;
Mohammadi, Bagher ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2008, (20) :3180-3182