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

Authors

  • Николай С. Зимницкий Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000
  • Алексей Ю. Барков Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000
  • Игорь Б. Кутяшев Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000
  • Владислав Ю. Коротаев Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000
  • Вячеслав Я. Сосновских Институт естественных наук и математики Уральского федерального университета им. первого Президента России Б. Н. Ельцина, пр. Ленина, 51, Екатеринбург 620000

DOI:

https://doi.org/10.1007/6270

Keywords:

azomethine ylides, (E)-1, 5-diarylpent-4-ene-1, 3-diones, L-phenylglycine, L-proline, spiro[acenaphthylenepyrroli(zi)din]-2-ones, L-thiaproline, 1, 3-dipolar cycloaddition

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

Downloads

Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers