One-pot approach to the synthesis of novel 12H-chromeno[2′,3′:4,5]imidazo[1,2-a]pyridines in aqueous media

被引：26

作者：

Proenca, M. Fernanda ^{[1
]}

Costa, Marta ^{[1
]}

机构：

[1] Univ Minho, Dept Chem, P-4710057 Braga, Portugal

来源：

TETRAHEDRON | 2010年 / 66卷 / 25期

关键词：

Salicylaldehyde; Pyridinium chloride; Chromene; Imidazo[1,2-a]pyridine; Cascade reaction; DERIVATIVES; INHIBITORS; COUMARINS; CHROMENE; DISCOVERY; PYRIDINE; BACE-1;

D O I：

10.1016/j.tet.2010.04.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chromeno-imidazo[1,2-a]pyridine scaffold was generated in an one pot condensation/cyclization reaction involving a salicylaldehyde and 1-(cyanomethyl)pyridinium chloride, in aqueous sodium carbonate solution. These novel compounds were isolated in 47-71% yield. The reaction pathway was followed by H-1 NMR spectroscopy allowing a clear understanding of the side reactions involved in the process. Different mono-substituted pyridinium chlorides were synthesized and reacted with mono-substituted salicylaldehydes and a detailed discussion of the scope of the synthetic method is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4542 / 4550

页数：9

相关论文

共 31 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] Antifungal activity of a novel chromene dimer [J].

Abrunhosa, L. ;

Costa, M. ;

Areias, F. ;

Venancio, A. ;

Proenca, F. .

JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY, 2007, 34 (12) :787-792

[3] DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].

ALMIRANTE, L ;

POLO, L ;

MUGNAINI, A ;

PROVINCIALI, E ;

RUGARLI, P ;

BIANCOTTI, A ;

GAMBA, A ;

MURMANN, W .

JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+

[4] A convenient synthesis of linear pyridinoimidazo[1,2-a] pyridine and pyrroloimidazo[1,2-a] pyridine cores [J].

Andaloussi, Mounir ;

Moreau, Emmanuel ;

Chavignon, Olivier ;

Teulade, Jean C. .

TETRAHEDRON LETTERS, 2007, 48 (47) :8392-8395

[5]

[Anonymous], 1904, Justus Liebigs Ann. Chem., V330, P361, DOI DOI 10.1002/JLAC.19043300217

[6] Naturally derived anti-HIV agents [J].

Asres, K ;

Seyoum, A ;

Veeresham, C ;

Bucar, F ;

Gibbons, S .

PHYTOTHERAPY RESEARCH, 2005, 19 (07) :557-581

[7]

BARTHOLINI G, 1993, LERS MONOGR, V8, P1

[8] Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase [J].

Brühlmann, C ;

Ooms, F ;

Carrupt, PA ;

Testa, B ;

Catto, M ;

Leonetti, F ;

Altomare, C ;

Carotti, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (19) :3195-3198

[9] IRAK-4 inhibitors.: Part III:: A series of imidazo[1,2-a] pyridines [J].

Buckley, George M. ;

Fosbeary, Richard ;

Fraser, Joanne L. ;

Gowers, Lewis ;

Higueruelo, Alicia P. ;

James, Lynwen A. ;

Jenkins, Kerry ;

Mack, Stephen R. ;

Morgan, Trevor ;

Parry, David M. ;

Pitt, William R. ;

Rausch, Oliver ;

Richard, Marianna D. ;

Sabin, Verity .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (12) :3656-3660

[10] Structural insights into monoamine oxidase inhibitory potency and selectivity of 7-substituted coumarins from ligand- and target-based approaches [J].

Catto, Marco ;

Nicolotti, Orazio ;

Leonetti, Francesco ;

Carotti, Andrea ;

Danilo Favia, Angelo ;

Soto-Otero, Ramon ;

Mendez-Alvarez, Estefania ;

Carotti, Angelo .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (16) :4912-4925

← 1 2 3 4 →