Аннотация:It was shown for the first time that monosubstituded cyclopropanes (like anylides of cyclopropanecarboxylic acid), deactivated respecting ring opening, in reaction with (Ph3P·CBr4) as halogenating agent can rearrange into N-phenylpyrrolidin-2-ones. It was stated that that transformation is possible only because imidoylbromides A as intermediates are formed in the reaction course. In the opinion of the authors, these intermediates in cyclopropane ring opening reactions are more active than parent carbonylcyclopropanes.
It is demonstrated in our study that anylides of cyclopropanecarboxylic acid in the presence of ammonium iodide can be rearranged into N-aryl- and heteroarylpyrrolidin-2-ones with high yields. Microwave irradiation during 15 - 30 min is used to carry out the reactions.
Synthesis of pyrrolidinones using procedure developed is more simple, cost-effective and is suitable for "green chemistry". Study of structures of key intermediates of the reaction proposed and searching for areas of this reaction using are in progress.