WAGNER–MEERWEIN REARRANGEMENT IN 2,6a-EPOXYOXIRENO[<i>e</i>]ISOINDOLE SERIES

Authors

  • Владимир П. Зайцев Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198
  • Федор И. Зубков Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198
  • Марьана А. Надирова Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198
  • Дмитрий Ф. Мерцалов Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198
  • Евгения В. Никитина Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198
  • Роман A. Новиков V. A. .Engel'gardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Вавилова St., Moscow 119991
  • Алексей В. Варламов Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

DOI:

https://doi.org/10.1007/3403

Keywords:

2, 6a-epoxyoxireno[e]isoindoles, 4, 6-epoxycyclopenta[c]pyridines, isoindole, intramolecular Diels–Alder reaction, Wagner–Meerwein rearrangement

Abstract

A cation-catalyzed Wagner–Meerwein skeletal rearrangement in octahydro-2,6a-epoxyoxireno[e]isoindole series was studied. It was shown that the reaction proceeds ambiguously when effected by boron trifluoride etherate in acetic anhydride: the target 4,5-bis(acetoxy)-4,6-epoxycyclopenta[c]pyridines as well as the products of their further degradation, cyclopenta[c]pyridines, were isolated from the reaction mixture in 10–15% yields as single diastereomers.

Authors: Vladimir P. Zaytsev*, Fedor I. Zubkov, Mar'yana A. Nadirova, Dmitriy F. Mertsalov, Eugeniya V. Nikitina, Roman A. Novikov, Alexey V. Varlamov

 

Author Biographies

Владимир П. Зайцев, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

Владимир Петрович Зайцев

Федор И. Зубков, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

Федор Иванович Зубков

Марьана А. Надирова, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

Марьана Альбертовна Надирова

Дмитрий Ф. Мерцалов, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

Дмитрий Федорович Мерцалов

Евгения В. Никитина, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

Евгения Валентиновна Никитина

Алексей В. Варламов, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198

Алексей Васильевич Варламов

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Published

2016-10-25

Issue

Vol. 52 No. 9 (2016): Pericyclic reactions in heterocyclic chemistry

Section

Original Papers