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

来源：

TETRAHEDRON | 2008年 / 64卷 / 47期

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

页码：10681 / 10686

页数：6

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
Adib, M
Sheibani, E
Mostofi, M
Ghanbary, K
Bijanzadeh, HR
[J]. 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
Adib, M
Ghanbary, K
Mostofi, M
Bijanzadeh, HR
[J]. TETRAHEDRON, 2005, 61 (10) : 2645 - 2648
[4] An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines
Adib, Mehdi
Sheibani, Esmail
Zhu, Long-Guan
Mirzaei, Peiman
[J]. 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
Adib, Mehdi
Mohammadi, Bagher
Bijanzadeh, Hamid Reza
[J]. 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
Adib, Mehdi
Mahdavi, Mohammad
Noghani, Mahsa Alizadeh
Bijanzadeh, Hamid Reza
[J]. 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
Adib, Mehdi
Sayahi, Mohammad Hosein
Ziyadi, Hakimeh
Bijanzadeh, Hamid Reza
Zhu, Long-Guan
[J]. TETRAHEDRON, 2007, 63 (45) : 11135 - 11140
[8] Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water
Adib, Mehdi
Mahdavi, Mohammad
Noghani, Mahsa Alizadeh
Mirzaei, Peiman
[J]. TETRAHEDRON LETTERS, 2007, 48 (41) : 7263 - 7265
[9] Efficient synthesis of imidazo[1,2-a]pyridin-3(2H)-ones
Adib, Mehdi
Mahdavi, Mohammad
Abbasi, Alireza
Jahromi, Amin Haghighat
Bijanzadeh, Hamid Reza
[J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3217 - 3220
[10] Krohnke pyridines: an efficient solvent-free synthesis of 2,4,6-triarylpyridines
Adib, Mehdi
Tahermansouri, Hasan
Koloogani, Somayeh Aah
Mohammadia, Bagher
Bijanzadeh, Hamid Reza
[J]. TETRAHEDRON LETTERS, 2006, 47 (33) : 5957 - 5960

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