Exocyclic-endocyclic n-acyliminium ion equilibration via an intramolecular α-thioamidoalkylation in the synthesis of fused N,S-heterocyclic systems: Some new parameters

European Journal of Organic Chemistry

Volumn , Issue 13, 2005, Pages 2758-2770

  Hucher, Nicolas ^a   Pesquet, Anthony ^a   Netchitaïlo, Pierre ^a   Daïch, Adam ^a  

^a UNIVERSITÉ DU HAVRE   (France)

Author keywords

Acyliminium ion; Isomerization; Nitrogen heterocycles; Sulfur heterocycles

Indexed keywords

EID: 22144482745     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400760     Document Type: Article

References (26)

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11. 4 gave only the corresponding 3-acetyloxyisoindolinone and 3-phenyl- thioisoindolinone 5, respectively. The latter product 5 was obtained by a successive process including i. the cleavage of the -N-CH-S- linkage obtained partially from hydroxy lactam 4, and ii. the intramolecular nucleophilic attack of the generated thiophenol on the endocyclic N-acyliminium ion of type B.
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