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Comptes Rendus Chimie
Volume 18, n° 4
pages 374-378 (avril 2015)
Doi : 10.1016/j.crci.2014.08.006
Received : 18 May 2014 ;  accepted : 25 August 2014
Solvent-free multicomponent synthesis of 2-arylpyridines using p -sulfonic acid calix[6]arene as a reusable catalyst
 

Ángel G. Sathicq a, Natália A. Liberto b, Sergio A. Fernándes b, Gustavo P. Romanelli a,
a Centro de Investigación y Desarrollo en Ciencias Aplicadas “Dr. Jorge J. Ronco” (CINDECA-CCT-CONICET), Universidad Nacional de La Plata, Calle 47 No 257, B1900AJK La Plata, Argentina 
b Grupo de Química Supramolecular e Biomimétrica (GQSB), Departamento de Química, Universidade Federal de Viçosa, Campus Universitário, Avenida P.H. Rolfs, s/n, Viçosa, MG 36570-000, Brazil 

Corresponding author.
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Abstract

An efficient methodology for obtaining 2-arylpyrimidines based on the use of p -sulfonic acid calix[6]arene as an organocatalyst is proposed. The methodology involves the formation of 1,2-dihydropyridine intermediates using a variety of aromatic aldehydes with methyl or ethyl acetoacetate and ammonium acetate, which are the same starting materials as in the Hantzsch reaction, under solvent-free reaction conditions, at 25°C, followed by air oxidation for 12h. The catalyst efficiency is not compromised after its successive use in reactions. Eleven examples were obtained with very good to excellent yields of 2-arylpyridines (92–62%). This is the first report about the use of calixarenes as catalysts in the multicomponent synthesis of 2-arylpyridines (molecules with potential biological activity).

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Keywords : 2-Arylpyridines, P -Sulfonic acid calix[6]arene, Organocatalyts, Solvent-free conditions, Oxidant-free conditions




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