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Synthèse par cyclisation nucléophile de dérivés de sucres portant un hétérocycle inséré en spiro. Note de Laboratoire

✍ Scribed by Jean M. J. Tronchet; Bernard Gentile

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
382 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of Sugar Derivatives Bearing a Spiro Heterocycle via Nucleophilic Cyclization

Treated 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, ‐oxazepine 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.

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