Synthesis and chemistry of 5, 6-dihydropyridinium salt adducts. Synthons for general electrophilic and nucleophilic substitution of the piperidine ring system

DS Grierson, M Harris, HP Husson

Index: Grierson,D.S.; Harris,M.; Husson,H.P. Journal of the American Chemical Society, 1980 , vol. 102, p. 1064

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Citation Number: 131

Abstract

Abstract: 5, 6-Dihydropyridinium salts 4a-f, readily available from the reaction of tetrahydropyridine N-oxides 3a-f with tri-fluoroacetic anhydride, gave nucleophilic addition adducts 5-8 when reacted with CN-, C6HjS-, C6H&H2S-, and (CH&NH under two-phase (water-CH2Clz) and/or nonaqueous reaction conditions. Regiospecific reaction of cyanide ion at C-2 of 4a-f gave the 2-cyano-3-piperideines 5a-f, whereas for C6HjS-, C6HjCHZS-, ...