Reaction of α,β-unsaturated imidates with Grignard reagents leading to 2-alkyl 1,3-diimines

Abstract

Methyl N-phenylacrylimidate (1a) reacted with alkyl- and aryl-magnesium bromides in ether at 0 °C to give 2-alkyl 1,3-diketones (3a) in a good yield after aqueous work-up; methyl N-phenylcrotonimidate (1b) and N-phenylcinnamimidate (1c) with alkylmagnesium bromides furnished analogous 1,3-diketones (3) as the major products after hydrolysis of the corresponding stable diimines (2).