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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 16
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Original Articles

Aromatization of Hantzsch 1,4-Dihydropyridines with Al(NO3)3·9H2O and/or Fe(NO3)3·9H2O in the Presence of Silica Sulfuric Acid Under Mild and Heterogeneous Conditions

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Pages 2457-2463 | Received 09 Jun 2009, Published online: 26 Jul 2010
 

Abstract

A simple and convenient method for the aromatization of Hantzsch 1,4-dihydropyridines to the corresponding pyridines is achieved via combination of aluminum or ferric nitrates and silica sulfuric acid as environmentally friendly and novel oxidizing media. This oxidation was carried out in dichloromethane under heterogeneous conditions with good to excellent yields.

ACKNOWLEDGMENT

The authors thank the research facilities of Ilam University, Ilam, Iran, for financial support of this research project.

Notes

a DHP/Fe(NO3)3·9H2O/SiO2·OSO3H = 1: 1.5 mmol: 0.2 g.

b Isolated yield.

c No reaction.

d Reaction did not complete.

a I refers to grams of silica sulfuric acid; II and III refer to mmol of aluminium nitrate and ferric nitrate respectively.

b Isolated yield. All products were identified by comparison with authentic samples (mp, IR, 1H NMR, and 13C NMR).

a Isolated yield.

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