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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Straightforward access to highly substituted nicotinic acid derivatives.</title><author><name sortKey="Robert, Nicolas" sort="Robert, Nicolas" uniqKey="Robert N" first="Nicolas" last="Robert">Nicolas Robert</name><affiliation wicri:level="4"><nlm:affiliation>Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR 6014, INSA et Université de Rouen, IRCOF-INSA Rouen BP08, 76131 Mont Saint Aignan Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR 6014, INSA et Université de Rouen, IRCOF-INSA Rouen BP08, 76131 Mont Saint Aignan Cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Mont Saint Aignan</settlement></placeName><orgName type="university">Université de Rouen</orgName></affiliation></author><author><name sortKey="Bonneau, Anne Laure" sort="Bonneau, Anne Laure" uniqKey="Bonneau A" first="Anne-Laure" last="Bonneau">Anne-Laure Bonneau</name></author><author><name sortKey="Hoarau, Christophe" sort="Hoarau, Christophe" uniqKey="Hoarau C" first="Christophe" last="Hoarau">Christophe Hoarau</name></author><author><name sortKey="Marsais, Francis" sort="Marsais, Francis" uniqKey="Marsais F" first="Francis" last="Marsais">Francis Marsais</name></author></analytic><series><title level="j">Organic letters</title><idno type="ISSN">1523-7060</idno><imprint><date when="2006" type="published">2006</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Lithium (chemistry)</term><term>Niacin (analogs & derivatives)</term><term>Niacin (chemistry)</term><term>Pyridines (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acide nicotinique ()</term><term>Acide nicotinique (analogues et dérivés)</term><term>Lithium ()</term><term>Pyridines ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Niacin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Lithium</term><term>Niacin</term><term>Pyridines</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Acide nicotinique</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acide nicotinique</term><term>Lithium</term><term>Pyridines</term></keywords></textClass></profileDesc></teiHeader><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. 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