Acenaphthenequinone-Based Stabilized Azomethine Ylides in (3+2) Cycloaddition Reactions with 1,5-diarylpent-4-ene-1,3-diones

Acenaphthenequinone-Based Stabilized Azomethine Ylides in (3+2) Cycloaddition Reactions with 1,5-diarylpent-4-ene-1,3-diones

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-a...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2021-08, Vol.57 (7-8), p.743-750
Hauptverfasser: Zimnitskiy, Nikolay S., Barkov, Alexey Yu, Kutyashev, Igor B., Korotaev, Vladislav Yu, Sosnovskikh, Vyacheslav Ya
Format: Artikel
Sprache:eng
Schlagworte:
Amino acids
Chemistry
Chemistry and Materials Science
Cycloaddition
Diketones
Organic Chemistry
Pharmacy
Proline
Schiff bases
Stereoselectivity
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Zusammenfassung: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-021-02978-4