IODINE ACETATE AS A MILD SELECTIVE AGENT FOR THE WAGNER–MEERWEIN REARRANGEMENT IN 3a,6-EPOXYISOINDOLES

Authors

  • Владимир П. Зайцев RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Дмитрий Ф. Мерцалов RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Анастасия M. Трунова RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Анастасия B. Ханова RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Евгения B. Никитина RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Анна A. Синельщикова RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Михаил C. Григорьев Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31/4 Leninskiy prosp., Moscow 119071

DOI:

https://doi.org/10.1007/5713

Keywords:

cyclopenta[c]pyridines, iodine acetate, isoindoles, IMDAF reaction, intramolecular Diels–Alder reaction, Wagner–Meerwein rearrangement

Abstract

The iodine-initiated cationic skeletal Wagner–Meerwein rearrangement in tetrahydro-3a,6-epoxyisoindol-1-ones has been studied. It was shown that by the action of iodine acetate in acetic anhydride the reaction proceeds regio- and stereoselectively with the formation of 5-iodo-4,6-epoxycyclopenta[c]pyridin-4-yl acetates. The proposed reagent provides better yields of rearrangement products than those described in the literature.

Authors: Vladimir P. Zaytsev*, Dmitriy F. Mertsalov, Anastasiya M. Trunova, Anastasiya V. Khanova, Eugeniya V. Nikitina, Anna А. Sinelshchikova, Mikhail S. Grigoriev

Downloads

Published

2020-08-20

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Original Papers