ChemInform Abstract: C‐GLYCOSYL DERIVATIVES. XL. SYNTHESIS OF SUGAR DERIVATIVES BEARING A SPIRO HETEROCYCLE VIA NUCLEOPHIC CYCLIZATION

Abstract

SummaryTreated with the 1,4-binucleophiles 1,2-diaminoethane, 2-aminoethanol, 2-aminoethanethiol, L-cysteine, o-phenylenediamine, o-aminophenol or o-aminothiophenol the ketosugar derivative 1 gave in good yields the corresponding spiro derivatives 2-8. In each case, the reaction was stereospecific leading to the isomer bearing the N-atom on the endo face of the bicyclic starting material. Starting from the sugar enone 9, the aromatic 1,4-binucleophiles led stereospecifically to the spirobenzo[b]-diazepine 10, -0xazepine 11 or -thiazepine 12. In one case, an imine (13) was isolated. As 13 cyclized to 6, the intermediate formation of these kind of derivatives could be considered as a common step for all these reactions.Nous avons rapporte dans une communication prkliminaire [2] que des spirohkterocycles etaient forrnks en bons rendements par action sur des osuloses gamines primaires aliphatiques ou aromatiques portant un second groupe nucleophile skparC du premier pardeuxatomesde carbone. Ainsi, a partir de 1 [3], on obtient avec des rendements compris entre 66 et 80%, les composks 2 a 8, alors que la benzodiazepine