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Jean-Gerard, L., Pauvert, M., Collet, S., Guingant, A. & Evain, M. (2007) A new enlargement methodology for the preparation of 2H-1-and 2H-3-benzazepin-2-one derivatives. Tetrahedron, 63 11250–11259. 
Added by: Laurent Cournède (2016-03-10 22:02:29)
Type de référence: Article
DOI: 10.1016/j.tet.2007.08.094
Numéro d'identification (ISBN etc.): 0040-4020
Clé BibTeX: JeanGerard2007
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Catégories: MIOPS
Mots-clés: 2H-1-and 2H-3-benzazepin-2-one derivatives, 429, asymmetric-synthesis, calcium-channel blockers, chiral primary amines, growth-hormone secretagogue, heterocycles, inhibitors, l-692, potent, ring enlargement, ring-expansion, zincke reaction
Créateurs: Collet, Evain, Guingant, Jean-Gerard, Pauvert
Collection: Tetrahedron
Consultations : 1/399
Indice de consultation : 1%
Indice de popularité : 0.25%
Résumé     
An investigation of the one-carbon homologation of some 1-tribromomethyl-isoquinoline and 2-tribromomethyl-quinoline derivatives was conducted. Under the influence of an aqueous solution of silver nitrate in the presence of a nucleophilic species (MeOH, H2O, EtNH2), these derivatives led to the respective expanded heterocycles, 2H-1- and 2H-3-benzazepin-2-one derivatives. A mechanism for this novel ring enlargement involving initial formation of an aziridinium, and its subsequent opening to form a stabilized benzylic carbocation, is proposed to explain the results. (C) 2007 Elsevier Ltd. All rights reserved.
Added by: Laurent Cournède  
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