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 pi-cyclisation.
Identifieur interne : 000131 ( Ncbi/Curation ); précédent : 000130; suivant : 000132Acid-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 pi-cyclisation.
Auteurs : Anthony Pesquet [France] ; Adam Daïch ; Bernard Decroix [France] ; Luc Van HijfteSource :
- 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, pi-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).
DOI: 10.1039/b508214e
PubMed: 16240011
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Havre</orgName></affiliation></author><author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name></author><author><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name><affiliation><country>France</country><placeName><settlement type="city">Le Havre</settlement><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region></placeName><orgName type="university" n="3">Université du Havre</orgName></affiliation></author><author><name sortKey="Van Hijfte, Luc" sort="Van Hijfte, Luc" uniqKey="Van Hijfte L" first="Luc" last="Van Hijfte">Luc Van Hijfte</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2005">2005</date><idno type="RBID">pubmed:16240011</idno><idno type="pmid">16240011</idno><idno type="doi">10.1039/b508214e</idno><idno 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Havre</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName><orgName type="university">Université du Havre</orgName></affiliation></author><author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name></author><author><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name><affiliation><country>France</country><placeName><settlement type="city">Le Havre</settlement><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region></placeName><orgName type="university" n="3">Université du Havre</orgName></affiliation></author><author><name sortKey="Van Hijfte, Luc" sort="Van Hijfte, Luc" uniqKey="Van Hijfte L" first="Luc" last="Van Hijfte">Luc Van Hijfte</name></author></analytic><series><title level="j">Organic & biomolecular chemistry</title><idno type="ISSN">1477-0520</idno><imprint><date when="2005" type="published">2005</date></imprint></series></biblStruct></sourceDesc></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></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">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, pi-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></record>Pour manipuler ce document sous Unix (Dilib)
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