Known reaction conditions to synthesize homodisubstituted pyridines through one-pot cyclization of aryl methyl ketones, ammonium salts, and DMSO were applied to the production of heterodisubstituted pyridines. As expected, 1:1 mixtures of alkyl and aryl ketones led to observation of homocoupling of the more reactive aryl ketones to give the major products. Reaction mixtures containing higher ratios of the less-reactive alkyl ketone directed the favorability of the reaction towards heterodisubstituted pyridines as evidenced by both <sup>1</sup>H NMR spectroscopy and mass spectrometry. Microwave heating was also tested as an alternative to pressure tube heating, and preliminary results showed cleaner product mixtures and a possible increase in reactivity of alkyl ketones. Continued studies were performed to examine the scope of the reaction and to optimize selectivity and yield.

Synthesis of heterodisubstituted pyridines via cyclization of methyl ketones, DMSO, and ammonium salts

253rd National Meeting (2017)

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