OPENING OF THE EPOXIDE BRIDGE IN 3a,6-EPOXYISOINDOL-1-ONES BY THE ACTION OF BF<sub>3</sub>&middot;Et<sub>2</sub>O IN ACETIC ANHYDRIDE

Authors

  • Ф. И. Зубков Peoples' Friendship University of Russia
  • В. П. Зайцев Peoples' Friendship University of Russia
  • Е. С. Пузикова Peoples' Friendship University of Russia
  • Е. В. Никитина Peoples' Friendship University of Russia
  • В. Н. Хрусталёв A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
  • Р. А. Новиков V. A. Engel'gardt Institute of Molecular Biology
  • А. В. Варламов Peoples' Friendship University of Russia

DOI:

https://doi.org/10.1007/1247

Keywords:

3a, 6-epoxyisoindole, furan, furfurylamine, isoindole, 7-oxabicyclo[2.2.1]heptene, aromatization, intramolecular Diels-Alder reaction

Abstract

The opening of the epoxide bridge in N-substituted 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-ones by the action of BF3·Et2O in acetic anhydride at 25°C over 1 h proceeds through an SN1 mechanism. The allylic type cation formed in the first step is stabilized by the addition of an acetoxy group at C-5 in the isoindole system to give a mixture of cis and trans isomers of 5,6-diacetoxy-2,3,5,6,7,7a-hexahydroisoindol-1-ones, which are aromatized under these conditions over 24 h to give 2,3-dihydro-1H-isoindol-1-ones.

Authors: F. I. Zubkov, V. P. Zaytsev, E. S. Puzikova, E. V. Nikitina, V. N. Khrustalev, R. A. Novikov, and A. V. Varlamov.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (3), pp 514-524

http://link.springer.com/article/10.1007/s10593-012-1024-0

Published

2013-11-27

Issue

Section

Original Papers