Abstract
3-Methyl-1H -quinoxalin-2-one has been doubly lithiated with n -butylithium at -78 °C in THF. The dilithio reagent thus obtained reacts with various electrophiles (iodomethane, iodoethane, D2 O, benzaldehyde, benzophenone, cyclohexanone) to give modified 3-substituted 1H -quinoxalin-2-ones in good yields. In the reaction of the dilithio reagent with phenyl isothiocyanate the product was a tautomer of the simple substitution product. Reaction of the dilithio reagent with iodine gives an oxidatively dimerised product instead of the 3-iodomethyl derivative. Lithiations of 3-ethyl- and 3-propyl-1H -quinoxalin-2-ones, followed by reactions with representative electrophiles (benzaldehyde, benzophenone, cyclohexanone), behaved in a similar manner to give the corresponding modified 3-substituted derivatives in good yields.
Key words
double lithiation - 1H -quinoxalin-2-ones - electrophiles - tautomerisation - oxidative dimerisation
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