Abstract
A route to spiroisoxazolinopiperidinylbenzamides has been developed. N-Boc-4-piperidone underwent a Wittig olefination and Boc-deprotection followed by a nucleophilic substitution reaction with 4-fluoro-3-nitrobenzoic acid to yield the starting scaffold 3 in excellent yields. Diversification of the acid with primary amines, followed nitrile oxide formation in situ (aryl oximes treated with bleach) and subsequent 1,3-dipolar cycloaddition to the exo-methylene moiety delivered the spiroisoxazolinopiperdines. Reduction of the arylnitro group followed by acylation with acid chlorides or reductive amination with aldehydes yielded the spiroisoxazolinopiperidinylbenzamide library.
Original language | English (US) |
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Pages (from-to) | 3019-3023 |
Number of pages | 5 |
Journal | Synlett |
Issue number | 18 |
DOIs | |
State | Published - 2009 |
Keywords
- Cycloaddition
- Isoxazolines
- Nitrile oxide
- Nucleophilic substitution
- Piperidines
ASJC Scopus subject areas
- Organic Chemistry