Laboratory implementation demonstrates efficient synthesis and characterization of dihydropyridine derivatives, suggesting educational benefits.
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.
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Bucholtz et al. (2012) studied this question.
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