ACENAPHTHENEQUINONE-BASED STABILIZED AZOMETHINE YLIDES IN (3+2) CYCLOADDITION REACTIONS WITH 1,5-DIARYLPENT-4-ENE-1,3-DIONES

Abstract

A regio- and stereoselective method for the synthesis of spiro[acenaphthylenepyrroli(zi)din]-2-ones containing a 1,3-diketone fragment in their structure in 57–93% yields was developed. The method is based on (3+2) cycloaddition of azomethine ylides generated in situ from acenaphthenequinone and α-amino acids (L-(thia)proline, L-phenylglycine) to (E)-1,5-diarylpent-4-ene-1,3-diones in EtOH at 60–70°C for 4–8 h.

Authors: Nikolay S. Zimnitskiy*, Alexey Yu. Barkov, Igor B. Kutyashev,
Vladislav Yu. Korotaev*, Vyacheslav Ya. Sosnovskikh