Cyclodesulfurization Reaction of Glycosyl Thioureides

Reactions of glycosyl isothiocyanates (1a, b, c) with diamines such as o-phenylenediamine, 2, 3-diaminopyridine or 5, 6-diamino-1, 3-dimethyluracil gave the corresponding glycosyl thioureides in good yields. Glycosyl thioureides were converted into N-glycosylaminobenzimidazoles (5a, b, c), N-glycosy...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1979/05/25, Vol.27(5), pp.1153-1158
Hauptverfasser: TAKAHASHI, HIROSHI, NIMURA, NORIYUKI, OBATA, NAKA, SAKAI, HITOMI, OGURA, HARUO
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Sprache:eng
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Zusammenfassung:Reactions of glycosyl isothiocyanates (1a, b, c) with diamines such as o-phenylenediamine, 2, 3-diaminopyridine or 5, 6-diamino-1, 3-dimethyluracil gave the corresponding glycosyl thioureides in good yields. Glycosyl thioureides were converted into N-glycosylaminobenzimidazoles (5a, b, c), N-glycosyl-3-deazapurine (6a) or N-glycosylaminotheophyllines (7a, b, c) in excellent yields through a cyclodesulfurization reaction.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.27.1153