Abstract
Doubly lithiated 3-pivaloylan noquinazolin-4(3H)-one reacts with carbon(II) oxide at 0degreesC to give 77% of a mixture of azetidinone and indole derivatives, each incorporating a diisopropylamide unit from lithium diisopropylamide used for lithiation. No analogous reaction occurs with doubly lithiated 3-acetyl-aminoquinazolin-4(3H)-one and 3-acyl-2-alkylquinazolin-4(3H)-one. Carbonylation of doubly lithiated 2-alkyl-3-aminoquinazolin-4(3H)-ones at 0degreesC results in deamination to give 2-alkylquinazolin-4(3H)-ones in good yields.