1,3-Dipolar cycloaddition of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones and nitrile oxides: An experimental and theoretical investigation

Mariia M. Efremova, Alexander P. Molchanov, Alexander S. Novikov, Galina L. Starova, Anna A. Muryleva, Alexander V. Slita, Vladimir V. Zarubaev

Research outputpeer-review

2 Citations (Scopus)

Abstract

Cycloaddition reactions of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones proceeds regio- and stereoselectively on the double bond of the N-allyl substituent giving substituted isoxazolidines with good yields. Regioselectivity of the cycloaddition of this dipolarophiles with nitrile oxides depends on the structure of unsaturated hydrocarbon scaffold and the reaction selectively leads to adducts on endocyclic or the double bond of the N-allyl substituent. DFT calculations were used to investigate the reasons of the selectivity.

Original languageEnglish
Article number131104
JournalTetrahedron
Volume76
Issue number15
Early online date6 Mar 2020
DOIs
Publication statusPublished - 10 Apr 2020

Scopus subject areas

  • Organic Chemistry
  • Drug Discovery
  • Biochemistry

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