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 : 001232 ( Main/Exploration ); précédent : 001231; suivant : 001233Acid-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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Le document en format XML
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<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>
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