1. Preparation of a Spiroisoxazolinopiperidinylbenzamide-Based Scaffold.
- Author
-
Milinkevich, Kristin A. and Kurth, Mark J.
- Subjects
- *
AMINES , *ORGANIC compounds , *ORGANONITROGEN compounds , *RING formation (Chemistry) , *CHEMICAL reactions - 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 scaffold3 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. [ABSTRACT FROM AUTHOR]- Published
- 2009
- Full Text
- View/download PDF