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Dérivés C-Glycosyliques XXXII. Synthèse de dérivés spiro-C-glycosylidéniques par cyclisation nucléophile. Communication préliminaire

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

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
174 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

C‐Glycosylic derivatives XXXII. Synthesis of spiro‐C‐glycosylidenic derivatives via nucleophilic cyclization.

On treatment with compounds bearing two nucleophilic groups as ethylenediamine, o‐phenylenediamine or their monooxa or monothia analogues, 1,2:5, 6‐di‐O‐isopropylidene‐α‐D‐ribo‐hexofuranos‐3‐ulose gave with excellent yields the corresponding spiro‐C‐glycosylidenic derivative; for example, when using o‐phenylenediamine, a spirobenzimidazoline (5) was obtained. The latter compound underwent, on oxidation, a ring expansion to a morpholinobenzimidazole (8). Spirobenzodiazepines, spirobenzooxazepines and spirobenzothiazepines were formed when applying the same type of cyclization reaction to 3‐C‐acetylmethylene‐3‐deoxy‐1,2:5,6‐di‐O‐isopropylidene‐α‐D‐ribo‐ and α‐D‐xylo‐hexofuranoses.

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