The Ring Transformation of Substituted Isoxazoline N-Oxides by Lewis Acids

Eisuke Kaji; Kiyobumi Takahashi; Shonosuke Zen; Hikaru Nakamura; Yöichi Iitaka

doi:10.3987/r-1983-01-0119

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The Ring Transformation of Substituted Isoxazoline N-Oxides by Lewis Acids

Article 1983 en

Authors

EK
Eisuke Kaji
KT
Kiyobumi Takahashi
SZ
Shonosuke Zen

Abstract

1 min read

4-Substituted 3,5-bis(methoxycarbony1)lsoxazoline N-oxides (1) reacted with Lewis acids, e .g .tltanium(1V) chloride in dlchloromethane to yield two different products, 3H-lndale derivatives (2) and fused fur-isoxazolme derivatives (7).TheiP Structures of the products were confirmed by way of chemical and spectral analyses as well as by the preparation of their further derivatives respectlrely.And also, single-crystal X-ray analysis of (7) showed the above-mentioned fused rmg-structure.Substituent effects of (1) and solvent effects for the reaction will be discussed in detail.The reaction mechanism of this ring transformation is also proposed.

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