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ISSN: 1430-4171 (electronic version)

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Abstract Volume 17 (2012) pp 125-127
DOI 10.1007/s00897122429a

A Green Multi-component Synthesis in Organic Chemistry Laboratory: A Hantzsch Dihydropyridine Synthesis and Oxidation to the Corresponding Pyridine

Kevin M. Bucholtz*, Jeffrey D. Hugdahl, Adam M. Kiefer, Kelly M. Kiefer, Amanda M. Santa Maria

Department of Chemistry, Mercer University, 1400 Coleman Avenue, Macon, GA 31207, bucholtz_km@mercer.edu
Received July 16, 2011. Accepted January 28, 2012.

Published: 15 June 2012

Abstract. A green and efficient synthesis of 3,5-diacetyl-1,4-dihydro-2,6-dimethylpyridine (a 1,4-dihydropyridine) and oxidation to 3,5-diacetyl-2,6-dimethylpyridine has been developed and implemented into a sophomore level organic chemistry laboratory course. The multi-component Hantzsch synthesis of formaldehyde, 2,4-pentanedione and ammonium acetate in water provides the corresponding 1,4-dihydropyridine in high yields after recrystallization from ethanol. Oxidative aromatization of the 1,4-dihydropyridine with hydrogen peroxide in the presence of catalytic amounts of iron(III) acetylacetonate generates the corresponding substituted pyridine. The products are characterized by ¹H NMR, IR, and melting point.

Key Words: Laboratories and Demonstrations; organic chemistry; aqueous solution chemistry; green chemistry; synthesis

(*) Corresponding author. (E-mail: bucholtz_km@mercer.edu)

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