Acid-catalysed formation of tricyclic N,S-acetals in imidazolinone series based on the use of the unprecedented N-acyliminium ion cascade reaction involving transposition, heterocyclisation and π-cyclisation
Identifieur interne : 000D00 ( France/Analysis ); précédent : 000C99; suivant : 000D01Acid-catalysed formation of tricyclic N,S-acetals in imidazolinone series based on the use of the unprecedented N-acyliminium ion cascade reaction involving transposition, heterocyclisation and π-cyclisation
Auteurs : Anthony Pesquet [France] ; Adam Daïch [France] ; Bernard Decroix [France] ; Luc Van Hijfte [France]Source :
- Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2005.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Acetals, Heterocyclic Compounds, 3-Ring, Imidazolines.
- Catalysis, Cyclization.
Abstract
4-Hydroxy-5,5-dimethylimidazolines tethered at N-1 to an aryl sulfide undergo an unprecedented acid-catalysed domino reaction, involving double methyl transposition, heterocyclisation, isomerisation of thiazetidinium ion and, finally, π-cyclisation. In this way a one-pot synthesis of original tricyclic N,S-acetals was developed. The same triheterocyclic products can be prepared also starting from the corresponding 5-hydroxy isomers (in this case the cascade of reactions does not involve methyl transposition).
Url:
DOI: 10.1039/b508214e
Affiliations:
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ISTEX:902BC411840601DAB8D8E6387C4090A8106F479ALe document en format XML
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Chem.</title><idno type="ISSN">1477-0520</idno><idno type="eISSN">1477-0539</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="2005">2005</date><biblScope unit="volume">3</biblScope><biblScope unit="issue">21</biblScope><biblScope unit="page" from="3937">3937</biblScope><biblScope unit="page" to="3947">3947</biblScope></imprint><idno type="ISSN">1477-0520</idno></series><idno type="istex">902BC411840601DAB8D8E6387C4090A8106F479A</idno><idno type="DOI">10.1039/b508214e</idno><idno type="ms-id">b508214e</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1477-0520</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetals (chemical synthesis)</term><term>Catalysis</term><term>Cyclization</term><term>Heterocyclic Compounds, 3-Ring (chemical synthesis)</term><term>Imidazolines (chemical synthesis)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Acetals</term><term>Heterocyclic Compounds, 3-Ring</term><term>Imidazolines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Cyclization</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">4-Hydroxy-5,5-dimethylimidazolines tethered at N-1 to an aryl sulfide undergo an unprecedented acid-catalysed domino reaction, involving double methyl transposition, heterocyclisation, isomerisation of thiazetidinium ion and, finally, π-cyclisation. In this way a one-pot synthesis of original tricyclic N,S-acetals was developed. The same triheterocyclic products can be prepared also starting from the corresponding 5-hydroxy isomers (in this case the cascade of reactions does not involve methyl transposition).</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><country name="France"><noRegion><name sortKey="Pesquet, Anthony" sort="Pesquet, Anthony" uniqKey="Pesquet A" first="Anthony" last="Pesquet">Anthony Pesquet</name></noRegion><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name><name sortKey="Pesquet, Anthony" sort="Pesquet, Anthony" uniqKey="Pesquet A" first="Anthony" last="Pesquet">Anthony Pesquet</name><name sortKey="Van Hijfte, Luc" sort="Van Hijfte, Luc" uniqKey="Van Hijfte L" first="Luc" last="Van Hijfte">Luc Van Hijfte</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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