Regiochemistry in addition of Grignard reagents to N, N′-dibenzylated 2-purinones

1,3-, 1,7-, 1,9- and 3,7-dibenzylpurin-2-one form stable adducts when reacted with Grignard reagents. Reaction took place in the purine 6- or 8-position, and substantial differences in the regiochemical outcome of the reactions were found among the isomers. Several new classes of purinones are descr...

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Bibliographic Details
Published in:Tetrahedron 1996-09, Vol.52 (40), p.12979-12992
Main Authors: Andresen, Geir, Gundersen, Lise-Lotte, Rise, Frode
Format: Article
Language:English
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Summary:1,3-, 1,7-, 1,9- and 3,7-dibenzylpurin-2-one form stable adducts when reacted with Grignard reagents. Reaction took place in the purine 6- or 8-position, and substantial differences in the regiochemical outcome of the reactions were found among the isomers. Several new classes of purinones are described here for the first time. The structure elucidations of the products were accomplished by HETCOR, COLOC, GA-HMQC and GA-HMBC NMR spectroscopy. Blindern, N-0315 Oslo, Norway. N, N′-Dibenzylated purin-2-ones form adducts when reacted with Grignard reagents. Substantial differences in the regiochemical outcome of the additions were found among the isomers. The adducts could easily be rearomatized, as shown for the 1,9-dibenzylated purin-2-one.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00779-X