The synthesis of 3-(alditol-1-yl)-1,2,4-triazolo[3,4- a]phthalazines

Condensation of 1-hydrazinophthalazine (hydralazine) with d-lyxose, d-ribose, d-xylose, d-mannose, and l-rhamnose gave the corresponding aldehydo-sugar phthalazin-l-ylhydrazones. dD-Arabinose and d-galactose, on the other hand, gave the corresponding 3-(alditol-l-yl)-1,2,4-triazolo[3,4- a]phthalazin...

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Bibliographic Details
Published in:Carbohydrate research 1981-09, Vol.95 (1), p.51-60
Main Authors: Shaban, Mohammed A.E., Ali, Raafat S., El-Badry, Sousan M.
Format: Article
Language:English
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Summary:Condensation of 1-hydrazinophthalazine (hydralazine) with d-lyxose, d-ribose, d-xylose, d-mannose, and l-rhamnose gave the corresponding aldehydo-sugar phthalazin-l-ylhydrazones. dD-Arabinose and d-galactose, on the other hand, gave the corresponding 3-(alditol-l-yl)-1,2,4-triazolo[3,4- a]phthalazines through the autodehydrogenative cyclization of the hydrazones. A rationale for this difference is discussed. Acetylation of the latter gave the poly- O-acetyl derivatives. Catalytic, dehydrogenative cyclization with palladium-on-charcoal, or acetylation, transforms the hydrazones into the triazolophthalazines, or their acetates. The mass spectra of the synthesized compounds were discussed.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)85294-5