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

descriptionPublicationkeyboard_double_arrow_right Article 01 Jun 2007 Spain English Publisher:Elsevier BVJournal:Tetrahedron, volume 63, pages 5,274-5,286 (issn: 0040-4020,

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Authors: Díaz-Gavilán, Mónica; Choquesillo-Lazarte, Duane; González-Pérez, J. M.; Gallo, Miguel A.; Espinosa, Antonio; Campos Rosa, Joaquín M.;

doi: 10.1016/j.tet.2007.03.155

handle: 10261/18538

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

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Abstract

The 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.

This study was supported by the Instituto de Salud Carlos III (Fondo de Investigaci on anitaria) through the project no. PI041206, and by the Junta de Andaluc ía through the Excellence Research Project no. 00636.

13 pages, 5 figures, 4 tables, Scheme 6.

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Spain

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Spanish National Research Council
Spain

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