1,5-DIARYLPENT-4-ENE-1,3-DIONES IN THE SYNTHESIS OF SPIRO[(THIA)PYRROLIZIDINE-3,3'-OXINDOLES] AND 1,3-DIARYL-5-SPIRO[OXINDOLE-3,3'-PYRROLIZIDIN-2'-YL]-1<i>H</i>-PYRAZOLES

Authors

  • Владислав Ю. Коротаев Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia
  • Николай С. Зимницкий Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia
  • Андрей Д. Деникаев Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia
  • Алексей Ю. Барков Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia
  • Игорь Б. Кутяшев Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia
  • Вячеслав Я. Сосновских Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia

DOI:

https://doi.org/10.1007/5959

Keywords:

(E)-1, 5-diarylpent-4-ene-1, 3-diones, azomethine ylides, pyrazoles, spiro[pyrrolizidine-3, 3'-oxindoles], 1, 3-dipolar cycloaddition.

Abstract

The three-component reaction of (E)-1,5-diarylpent-4-ene-1,3-diones, isatins, and (thia)proline in i-PrOH at room temperature proceeds regio- and stereoselectively leading to the formation of spiro[(thia)pyrrolizidine-3,3'-oxindoles] with the 1,3-dicarbonyl moiety in the (thia)pyrrolizidine ring. Subsequent treatment of these tetracyclic products with arylhydrazine hydrochlorides under reflux in the EtOH–AcOH system gave 5-substituted 1,3-diaryl-1H-pyrazoles in high yields.

Author Biography

Владислав Ю. Коротаев, Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000, Russia

ведущий научный сотрудник отдела химического материаловедения

Published

2021-01-26

Issue

Section

Original Papers