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Synthesis of Isoxazoline Derivatives through Boulton–Katritzky Rearrangement of 1,2,4‐Oxadiazoles
Author(s) -
Palumbo Piccionello Antonio,
Guarcello Annalisa,
Pace Andrea,
Buscemi Silvestre
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201308
Subject(s) - chemistry , side chain , sigmatropic reaction , rearrangement reaction , oxadiazole , cope rearrangement , chain (unit) , carroll rearrangement , stereochemistry , organic chemistry , catalysis , polymer , physics , astronomy
The base‐induced rearrangement of 1,2,4‐oxadiazoles into isoxazoline derivatives is reported. This represents the first example of a three‐atom side‐chain rearrangement that involves a saturated CCO side chain at C‐3 of the oxadiazole. Nonaromatic 3‐amino‐isoxazoline derivatives are obtained in good yields. Interestingly, this reaction occurs through the rearrangement of aromatic oxadiazoles to form less stable bonds than those that are broken.