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

Владимир П. Зайцев, Федор И. Зубков, Марьана А. Надирова, Дмитрий Ф. Мерцалов, Евгения В. Никитина, Роман A. Новиков, Алексей В. Варламов
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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

 


Keywords


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

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