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Iodine Acetate as a Mild Selective Agent for the Wagner–Meerwein Rearrangement in 3a,6-Epoxyisoindoles
Chemistry of Heterocyclic Compounds ( IF 1.5 ) Pub Date : 2020-08-22 , DOI: 10.1007/s10593-020-02752-y
Vladimir P. Zaytsev , Dmitriy F. Mertsalov , Anastasiya M. Trunova , Anastasiya V. Khanova , Eugeniya V. Nikitina , Anna А. Sinelshchikova , Mikhail S. Grigoriev

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.


中文翻译:

乙酸碘作为3a,6-环氧异吲哚中Wagner-Meerwein重排的温和选择剂

已经研究了碘在四氢3a,6-环氧异吲哚-1-酮中引发的阳离子骨架Wagner-Meerwein重排。结果表明,通过乙酸碘在乙酸酐中的作用,该反应在区域和立体选择性上进行,形成了乙酸5-碘-4,6-环氧环戊[ c ]吡啶-4-基。所提出的试剂提供了比文献所述更好的重排产物产率。
更新日期:2020-08-22
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