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Acenaphthenequinone-Based Stabilized Azomethine Ylides in (3+2) Cycloaddition Reactions with 1,5-diarylpent-4-ene-1,3-diones
Chemistry of Heterocyclic Compounds  (IF1.277),  Pub Date : 2021-09-06, DOI: 10.1007/s10593-021-02978-4
Zimnitskiy, Nikolay S., Barkov, Alexey Yu., Kutyashev, Igor B., Korotaev, Vladislav Yu., Sosnovskikh, Vyacheslav Ya.

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.