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Iodoxybenzoic Acid (IBX): An Efficient and Novel Oxidizing Agent for the Aromatization of 1,4-Dihydropyridines

J. S. Yadav*, B. V. S. Reddy, A. K. Basak, G. Baishya, A. Venkat Narsaiah

*Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India, Email: jsyadaviict.res.in

J. S. Yadav, B. V. S. Reddy, A. K. Basak, G. Baishya, A. V. Narsaiah, Synthesis, 2006, 451-454.

DOI: 10.1055/s-2005-918519


Abstract

Hantzsch 1,4-dihydropyridines undergo smooth aromatization catalyzed by iodoxybenzoic acid (IBX) to afford the corresponding pyridine derivatives in high yields. All the reactions were carried out in DMSO solvent at 80-85 °C for a period of two to four hours to complete conversion of the substrates.

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Details

IBX could function as an efficient oxidant for the aromatization of Hantzsch 1,4-dihydropyridines. This method offers significant advantages such as the use of inexpensive, air- and moisture- stable oxidant, mild reaction conditions and compatibility with a variety of substituents present in the dihydropyridine skeleton, and easy workup procedure for the isolation of products.


Key Words

hypervalent iodine reagents, iodoxybenzoic acid, dihydropyridines, aromatization, DMSO, pyridine derivatives


ID: J66-Y2006-360