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Synthesis and reactivity of (RS)-6-chloro-7- or 9-(1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl)-7H- or 9H-purines bearing a nitrobenzenesulfonyl group on the nitrogen atom

AuthorsDíaz-Gavilán, Mónica; Choquesillo-Lazarte, Duane ; González-Pérez, J. M.; Gallo, Miguel A.; Espinosa, Antonio; Campos Rosa, Joaquín M.
Issue Date11-Jun-2007
CitationTetrahedron 63(24): 5274-5286 (2007)
AbstractThe O,O-acetalic compounds (RS)-3-methoxy-1-[(2)- or (4)-nitrobenzenesulfonyl)]-1,2,3,5-tetrahydro-4,1-benzoxazepine have been studied in the Lewis acid-mediated condensation with 6-chloropurine. 6-Chloropurine leads to the N-7″ aminalic bond in the cyclic products and mainly to the N-9″ aminalic bond in the acyclic ones. Substitution of the chlorine atom at the 6″ position of the purine moiety is more feasible when the ring is alkylated at N-7″ than at N-9″. Exchange with a hydroxyl group is performed with water traces in deuterated dimethylsulfoxide at room temperature in a solvent-mediated process. The exchange with strong nucleophiles (e.g., thiophenol) does not need further activation.
Description13 pages, 5 figures, 4 tables, Scheme 6.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2007.03.155
Appears in Collections:(IACT) Artículos
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