Heterocycle stabilized carbanions. Two series of anomalous products from 1-alkyl-4,6-diphenyl-2-pyridones

Abstract

1-Methyl-,1-ethyl, and 1-n-butyl-4,6-diphenyl-2-pyridones with lithium di-isopropylamide yield normal products with ketone and aldehydes as electrophiles, but dimeric derivatives with acid chlorides, esters, and alkyl halides. The alkylpyridones react with ethyl- and n-butyl-lithium and an electrophile to give products resulting from alkylation at the 3- and reaction with electrophile at the 4-position. Structures are supported by spectra and reaction mechanisms discussed.