关键词:
3H-quinazolin-4-one
nucleophilic addition
bromine-lithium exchange
dilithio reagent
electrophiles
摘要:
6-Methyl-3H-quinazolin-4-one reacted with alkyllithium reagents at -78degreesC in THF to give 2-alkyl-1,2-dihydro-6-methyl-3H-quinazolin-4-ones in high yields. However, no reaction took place when LDA was used as the lithium reagent. 6-Bromo-3H-quinazolin-4-one reacted with excessive butyllithium to give 2-butyl-1,2-dihydro-3H-quinazolin-4-ones in very good yields. However, the lithiation of 6-bromo-3H-quinazolin-4-one was achieved by the use of a combination of methyllithium (1.1 equivalents) and tert-butyllithium (2.2 equivalents) at -78degreesC in THF. The dilithio reagent thus obtained reacted with a variety of electrophiles (H2O, iodoethane, benzaldehyde, anisaldehyde, cyclohexanone, 2-hexanone, benzophenone, phenyl isothiocyanate, TITD) to give the corresponding 6-substituted 3H-quinazolin-4-ones in excellent yields. Reaction of the dilithio reagent with 1,3-dibromopropane gave 6,6'-(propanediyl)bis(3H-quinazolin-4-one).