3-Cyano-1-methylpyridinium iodide added to aq. NaOH and stirred for 2 h gave the isomeric 1,4-, 1,2-, and 1,6-dihydropyridines in the ratio 11:2:1, 5-cyano-1-methyl-2-pyridone, and 3-cyano-1-methyl-2-pyridone which were extd. with CH2Cl2. The aq. layer, after neutralization with H2SO4, gave 2-cyano-glutaconaldehyde Na enolate, shown by NMR to exist in a mesomeric state. The intermediate 2-hydroxydihydropyridines behaved as reducing agents toward the pyridinium cation, involving H- transfer, as well as undergoing the normal ring opening reaction.
Dihydropyridines and pyridones from 3-cyano-1-methylpyridinium iodide in aqueous sodium hydroxide / MICHELETTI MORACCI, Franco; Casini, Antonio; Liberatore, Felice; Carelli, Vincenzo. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 17:(1976), pp. 3723-3724.
Dihydropyridines and pyridones from 3-cyano-1-methylpyridinium iodide in aqueous sodium hydroxide.
MICHELETTI MORACCI, Franco;CASINI, Antonio;LIBERATORE, Felice;CARELLI, Vincenzo
1976
Abstract
3-Cyano-1-methylpyridinium iodide added to aq. NaOH and stirred for 2 h gave the isomeric 1,4-, 1,2-, and 1,6-dihydropyridines in the ratio 11:2:1, 5-cyano-1-methyl-2-pyridone, and 3-cyano-1-methyl-2-pyridone which were extd. with CH2Cl2. The aq. layer, after neutralization with H2SO4, gave 2-cyano-glutaconaldehyde Na enolate, shown by NMR to exist in a mesomeric state. The intermediate 2-hydroxydihydropyridines behaved as reducing agents toward the pyridinium cation, involving H- transfer, as well as undergoing the normal ring opening reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
