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

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作者
Nikolay S. Zimnitskiy
Alexey Yu. Barkov
Igor B. Kutyashev
Vladislav Yu. Korotaev
Vyacheslav Ya. Sosnovskikh
机构
[1] Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin,
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关键词
azomethine ylides; (; )-1,5-diarylpent-4-ene-1,3-diones; L-phenylglycine; L-proline; spiro[acenaphthylenepyrroli(zi)din]-2-ones; L-thiaproline; 1,3-dipolar cycloaddition;
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摘要
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.
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页码:743 / 750
页数:7
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