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 : 000306 ( PubMed/Curation ); précédent : 000305; suivant : 000307Acid-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 ; 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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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><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">16240011</PMID><DateCreated><Year>2005</Year><Month>10</Month><Day>21</Day></DateCreated><DateCompleted><Year>2007</Year><Month>06</Month><Day>06</Day></DateCompleted><DateRevised><Year>2005</Year><Month>10</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">1477-0520</ISSN><JournalIssue CitedMedium="Print"><Volume>3</Volume><Issue>21</Issue><PubDate><Year>2005</Year><Month>Nov</Month><Day>7</Day></PubDate></JournalIssue><Title>Organic & biomolecular chemistry</Title><ISOAbbreviation>Org. Biomol. Chem.</ISOAbbreviation></Journal><ArticleTitle>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.</ArticleTitle><Pagination><MedlinePgn>3937-47</MedlinePgn></Pagination><Abstract><AbstractText>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. 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