Unusual sterically controlled regioselective lithiation of 3-bromo-5-(4,4'-dimethyl)oxazolinylpyridine. Straightforward access to highly substituted nicotinic acid derivatives.
Identifieur interne : 000103 ( Ncbi/Checkpoint ); précédent : 000102; suivant : 000104Unusual sterically controlled regioselective lithiation of 3-bromo-5-(4,4'-dimethyl)oxazolinylpyridine. Straightforward access to highly substituted nicotinic acid derivatives.
Auteurs : Nicolas Robert [France] ; Anne-Laure Bonneau ; Christophe Hoarau ; Francis MarsaisSource :
- Organic letters [ 1523-7060 ] ; 2006.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Acide nicotinique.
- Acide nicotinique, Lithium, Pyridines.
English descriptors
- KwdEn :
- MESH :
Abstract
[Structure: see text] Lithiation of 5-bromonicotinic acid protected as secondary or tertiary amide as well as (4,4'-dimethyl)oxazoline with lithium amides is reported. The unusual C-2 and C-4 regioselective lithiation of 3-bromo-5-(4,4'-dimethyl)oxazolinylpyridine using LTMP versus LDA was observed, providing a new route to substituted nicotinic acid scaffolds. The methodology was applied to the synthesis of novel C-4 and C-6 arylated 5-bromonicotinic acids.
DOI: 10.1021/ol062556i
PubMed: 17165932
Affiliations:
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pubmed:17165932Le document en format XML
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<front><div type="abstract" xml:lang="en">[Structure: see text] Lithiation of 5-bromonicotinic acid protected as secondary or tertiary amide as well as (4,4'-dimethyl)oxazoline with lithium amides is reported. The unusual C-2 and C-4 regioselective lithiation of 3-bromo-5-(4,4'-dimethyl)oxazolinylpyridine using LTMP versus LDA was observed, providing a new route to substituted nicotinic acid scaffolds. The methodology was applied to the synthesis of novel C-4 and C-6 arylated 5-bromonicotinic acids.</div>
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