A heavy metal- and oxidant-free, one-pot synthesis of pyridines and fused pyridines based on a Lewis acid-catalyzed multicomponent reaction

被引：22

作者：

Alex Raja, V. P. ^{[1
,2
]}

Tenti, Giammarco ^{[1
]}

Perumal, Subbu ^{[2
]}

Carlos Menendez, J. ^{[1
]}

机构：

[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

[2] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 82期

关键词：

POLYSUBSTITUTED PYRIDINES; REGIOSELECTIVE SYNTHESIS; CYCLOADDITION; DERIVATIVES; ACCESS;

D O I：

10.1039/c4cc01791a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The InCl3-catalyzed sequential multicomponent reaction between 2-furfurylamine, beta-dicarbonyl compounds and alpha,beta-unsaturated aldehydes in ethanol, followed by microwave irradiation in solvent-free conditions, afforded good to excellent yields of highly substituted pyridines, with loss of a 2-furylmethyl side chain. The method was also adapted to the synthesis of quinolones, isoquinolines, phenanthridines and more complex fused pyridine systems.

引用

页码：12270 / 12272

页数：3

共 38 条

[1] Use of β,γ-Unsaturated α-Ketocarbonyls for a Totally Regioselective Oxidative Multicomponent Synthesis of Polyfunctionalized Pyridines [J].

Allais, Christophe ;

Constantieux, Thierry ;

Rodriguez, Jean .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :12945-12948

[2]

[Anonymous], TOP HETEROCYCL CHEM

[3] The bohimann-rahtz pyridine synthesis: From discovery to applications [J].

Bagley, Mark C. ;

Glover, Christian ;

Merritt, Eleanor A. .

SYNLETT, 2007, (16) :2459-2482

[4] Multicomponent and one-pot synthesis of trisubstituted pyridines through a Pd-catalyzed cross-coupling/cross-coupling/cycloaddition sequence [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Fernandez, M. Alejandro ;

Aznar, Fernando ;

Valdes, Carlos .

TETRAHEDRON, 2008, 64 (05) :778-786

[5] Bis(tridentate) Ruthenium-Terpyridine Complexes Featuring Microsecond Excited-State Lifetimes [J].

Brown, Douglas G. ;

Sanguantrakun, Nawaporn ;

Schulze, Benjamin ;

Schubert, Ulrich S. ;

Berlinguette, Curtis P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12354-12357

[6] Redox Economy in Organic Synthesis [J].

Burns, Noah Z. ;

Baran, Phil S. ;

Hoffmann, Reinhard W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867

[7] Three-Component Coupling Sequence for the Regiospecific Synthesis of Substituted Pyridines [J].

Chen, Ming Z. ;

Micalizio, Glenn C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1352-1356

[8] Scope of a novel three-component synthesis of highly functionalized pyridines [J].

Dash, Jyotirmayee ;

Lechel, Tilman ;

Reissig, Hans-Ulrich .

ORGANIC LETTERS, 2007, 9 (26) :5541-5544

[9] A New and Flexible Synthesis of 4-Hydroxypyridines: Rapid Access to Caerulomycins A, E and Functionalized Terpyridines [J].

Dash, Jyotirmayee ;

Reissig, Hans-Ulrich .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6811-6814

[10] Coupling-isomerization-enamine addition-cyclocondensation sequences:: A multicomponent approach to substituted and annelated pyridines [J].

Dediu, OG ;

Yehia, NAM ;

Oeser, T ;

Polborn, K ;

Müeller, TJJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (09) :1834-1848

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