An unexpected reaction of pyridine with acetyl chloride to give dihydropyridine and piperidine derivatives |
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Authors: | Pietro Spanu Alberto MannuFausta Ulgheri |
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Institution: | Istituto di Chimica Biomolecolare—Consiglio Nazionale delle Ricerche, Trav. La Crucca No 3, 07100 Sassari, Italy |
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Abstract: | An unexpected reaction of pyridine with acetyl chloride to give N-acetyl-1,2 and 1,4-dihydropyridyl acetic acid (1, 2) in high yield and regioselectivity has been reported. The key step is the formation of a zwitterionic pyridinium ketene enolate. The effect of different activating agents on the reaction yield and selectivity has been studied. Platinum(IV) mediated hydrogenation of the corresponding methyl esters (7, 8) gave piperidine derivatives (9, 10). |
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Keywords: | N-Acyl pyridinium salts Zwitterionic ketene enolate Dihydropyridine Piperidine |
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