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) |
|---|---|
| Pages (from-to) | 3019-3023 |
| Number of pages | 5 |
| Journal | Synlett |
| Issue number | 18 |
| DOIs | |
| State | Published - 2009 |
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Keywords
- Cycloaddition
- Isoxazolines
- Nitrile oxide
- Nucleophilic substitution
- Piperidines
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Preparation of a spiroisoxazolinopiperidinylbenzamide-based scaffold. / Milinkevich, Kristin A.; Kurth, Mark J.
In: Synlett, No. 18, 2009, p. 3019-3023.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Preparation of a spiroisoxazolinopiperidinylbenzamide-based scaffold
AU - Milinkevich, Kristin A.
AU - Kurth, Mark J.
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
KW - Cycloaddition
KW - Isoxazolines
KW - Nitrile oxide
KW - Nucleophilic substitution
KW - Piperidines
UR - http://www.scopus.com/inward/record.url?scp=72149098601&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=72149098601&partnerID=8YFLogxK
U2 - 10.1055/s-0029-1218290
DO - 10.1055/s-0029-1218290
M3 - Article
SP - 3019
EP - 3023
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 18
ER -