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

Владимир П. Зайцев, Дмитрий Ф. Мерцалов, Анастасия M. Трунова, Анастасия B. Ханова, Евгения B. Никитина, Анна A. Синельщикова, Михаил C. Григорьев
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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


Keywords


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

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