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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 21
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Original Articles

Efficient Oxidation of Hantzsch 1,4-Dihydropyridines with Tetrabutylammonium Peroxomonosulfate Catalyzed by Manganese(III) Schiff Base Complexes: The Effect of Schiff Base Complex on the Product Selectivity

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Pages 3867-3879 | Received 23 Jan 2009, Published online: 07 Oct 2009
 

Abstract

Efficient and rapid oxidation of Hantzsch 1,4-dihydropyridine with tetrabutylammonium peroxomonosulfate (TBAO) is reported. The Mn(salophen)/monopersulfate catalytic system efficiently converts 1,4-dihydropyridines (DHPs) to their corresponding pyridine derivatives under mechanical stirring and microwave irradiation in CH2Cl2. The ability of various Schiff base complexes to oxidize DHPs was also investigated. The results showed that in the presence of manganese Schiff complex, no by-product was obtained.

ACKNOWLEDGMENT

The partial support of this work by Yasouj University Council of Research is acknowledged.

Notes

a Reaction conditions: 4-phenyl derivative of 1,4-dihydropyridines (1 mmol), TBAO (2 mmol), catalyst (0.067 mmol), and CH2Cl2 (10 mL).

b Isolated yield.

a All products were identified by comparison with authentic samples (IR, 1H NMR, mp). Reaction conditions are TBAO (2 mmol), DHP (1 mmol), and Mn–salophen (0.067 mmol) in CH2Cl2 (10 mL).

b Isolated yields.

c The yields are in the absence of catalyst.

d The product is a dealkylated pyridine derivative.

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