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

被引:60
作者
Abid, Mehdi [1 ]
Sheibani, Esmail [1 ]
Bijanzadeh, Hamid Reza [2 ]
Zhu, Long-Guan [3 ]
机构
[1] Univ Tehran, Sch Chem, Univ Coll Sci, Tehran, Iran
[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[3] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
2-Aminopyridines; 2-Aminopyrazine; 2-Aminopyrimidine; Benzaldehydes; Imidazoline-2,4,5-trione; 3-Amino-2-arylimidazo[1,2-a]pyridines; 3-Amino-2-arylimidazo[1,2-a]pyrazines; 3-Amino-2-arylimidazo[1,2-a]pyrimidines; Multi-component reactions;
D O I
10.1016/j.tet.2008.09.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, one-pot, multi-component synthesis of 3-amino-2-arylmidazo[1,2-a]pyridines, 3-amino-2-arylimidazo[1,2-a]pyrazines, and 3-amino-2-arylimidazo[1,2-a]pyrimidines is described. Heating a Mixture of a 2-aminopyridine, 2-aminopyrazine or 2-aminopyrimidine, a benzaldehyde, and imidazoline-2,4,5-trione Under solvent-free conditions afforded imine derivatives of the title compounds in excellent yields. Single-crystal X-ray analysis conclusively confirms the structure of these bridgehead bicyclic 5-6 heterocycles. (C) 2008 Published by Elsevier Ltd.
引用
收藏
页码:10681 / 10686
页数:6
相关论文
共 33 条
[1]  
ABIGNENTE E, 1987, FARMACO, V42, P657
[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]   Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 4,5-diphenyl-1,3-dihydro-2H-imidazol-2-one.: One-pot synthesis of 5H-imidazo[2,1-b][1,3]oxazine derivatives [J].
Adib, M ;
Ghanbary, K ;
Mostofi, M ;
Bijanzadeh, HR .
TETRAHEDRON, 2005, 61 (10) :2645-2648
[4]   An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines [J].
Adib, Mehdi ;
Sheibani, Esmail ;
Zhu, Long-Guan ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (34) :5108-5110
[5]   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
[6]   Reaction between isocyanides and chalcones: an effcient solvent-free synthesis of 5-hydroxy-3,5-diaryl-1,5dihydro-2H-pyrrol-2-ones [J].
Adib, Mehdi ;
Mahdavi, Mohammad ;
Noghani, Mahsa Alizadeh ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2007, 48 (45) :8056-8059
[7]   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
[8]   Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water [J].
Adib, Mehdi ;
Mahdavi, Mohammad ;
Noghani, Mahsa Alizadeh ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2007, 48 (41) :7263-7265
[9]   Efficient synthesis of imidazo[1,2-a]pyridin-3(2H)-ones [J].
Adib, Mehdi ;
Mahdavi, Mohammad ;
Abbasi, Alireza ;
Jahromi, Amin Haghighat ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2007, 48 (18) :3217-3220
[10]   Krohnke pyridines: an efficient solvent-free synthesis of 2,4,6-triarylpyridines [J].
Adib, Mehdi ;
Tahermansouri, Hasan ;
Koloogani, Somayeh Aah ;
Mohammadia, Bagher ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2006, 47 (33) :5957-5960