Synthesis of 4-perfluoroalkylquinolines
Identifieur interne : 001E54 ( Main/Exploration ); précédent : 001E53; suivant : 001E55Synthesis of 4-perfluoroalkylquinolines
Auteurs : Lucjan Strekowski [États-Unis] ; Shou-Yuan Lin [États-Unis] ; Hyeran Lee [États-Unis] ; Zhi-Qin Zhang [États-Unis] ; J. Christian Mason [États-Unis]Source :
- Tetrahedron [ 0040-4020 ] ; 1998.
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Abstract
Abstract: 4-(Cn−1F2n−1)-Substituted quinolines (n = 2–4) are obtained by the reaction of 2-(CnF2n+1)-substituted anilines 1 with lithium enolate of acetaldehyde. A similar treatment of 1 with lithium enolates of methyl ketones, the treatment of 1 with lithium phenylacetylide or cyclization of ketimines derived from 1 and aryl methyl ketones furnish the corresponding 2-aryl-4-perfluoroalkylquinolines. The reaction of 1 with lithiated carbonitriles RCH(Li)CN (R = H, alkyl) provides an easy access to 2-amino-4-perfluoroalkyl-3-R-quinolines.
Url:
DOI: 10.1016/S0040-4020(98)00440-2
Affiliations:
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Christian Mason</name><affiliation wicri:level="1"><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303</wicri:regionArea><wicri:noRegion>Georgia 30303</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="ISSN">0040-4020</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1998">1998</date><biblScope unit="volume">54</biblScope><biblScope unit="issue">28</biblScope><biblScope unit="page" from="7947">7947</biblScope><biblScope unit="page" to="7954">7954</biblScope></imprint><idno type="ISSN">0040-4020</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4020</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aromatic protons</term><term>Calcd</term><term>Chem</term><term>Crude mixtures</term><term>Cyclization</term><term>Easy access</term><term>Enolate</term><term>Hrms</term><term>Lithium</term><term>Lithium enolate</term><term>Lithium enolates</term><term>Lithium phenylacetylide</term><term>Mass calcd</term><term>Methyl ketones</term><term>Mmol</term><term>Pure products</term><term>Single isomer</term><term>Standard workup</term><term>Strekowski</term><term>Tetrahedron</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Aromatic protons</term><term>Calcd</term><term>Chem</term><term>Crude mixtures</term><term>Cyclization</term><term>Easy access</term><term>Enolate</term><term>Hrms</term><term>Lithium</term><term>Lithium enolate</term><term>Lithium enolates</term><term>Lithium phenylacetylide</term><term>Mass calcd</term><term>Methyl ketones</term><term>Mmol</term><term>Pure products</term><term>Single isomer</term><term>Standard workup</term><term>Strekowski</term><term>Tetrahedron</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: 4-(Cn−1F2n−1)-Substituted quinolines (n = 2–4) are obtained by the reaction of 2-(CnF2n+1)-substituted anilines 1 with lithium enolate of acetaldehyde. A similar treatment of 1 with lithium enolates of methyl ketones, the treatment of 1 with lithium phenylacetylide or cyclization of ketimines derived from 1 and aryl methyl ketones furnish the corresponding 2-aryl-4-perfluoroalkylquinolines. The reaction of 1 with lithiated carbonitriles RCH(Li)CN (R = H, alkyl) provides an easy access to 2-amino-4-perfluoroalkyl-3-R-quinolines.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Massachusetts</li></region><settlement><li>Amherst (Massachusetts)</li></settlement><orgName><li>Université du Massachusetts</li></orgName></list><tree><country name="États-Unis"><noRegion><name sortKey="Strekowski, Lucjan" sort="Strekowski, Lucjan" uniqKey="Strekowski L" first="Lucjan" last="Strekowski">Lucjan Strekowski</name></noRegion><name sortKey="Lee, Hyeran" sort="Lee, Hyeran" uniqKey="Lee H" first="Hyeran" last="Lee">Hyeran Lee</name><name sortKey="Lin, Shou Yuan" sort="Lin, Shou Yuan" uniqKey="Lin S" first="Shou-Yuan" last="Lin">Shou-Yuan Lin</name><name sortKey="Lin, Shou Yuan" sort="Lin, Shou Yuan" uniqKey="Lin S" first="Shou-Yuan" last="Lin">Shou-Yuan Lin</name><name sortKey="Mason, J Christian" sort="Mason, J Christian" uniqKey="Mason J" first="J. Christian" last="Mason">J. Christian Mason</name><name sortKey="Zhang, Zhi Qin" sort="Zhang, Zhi Qin" uniqKey="Zhang Z" first="Zhi-Qin" last="Zhang">Zhi-Qin Zhang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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