Sugar 1,3,4-Oxadiazoles. Iv: The Synthesis of Sugar 1,3,4-Oxadiazoline Derivatives

Opianic acid reacts with various hydrazines to yield either hydrazone (3, 6) or phthalazinone (4) derivatives depending upon the electronic properties of the substituent attached to the hydrazine molecule. Oxidative cyclization of opianic acid aroylhydrazones with iodine and yellow mercuric oxide gave the 1,3,4‐oxadiazole derivatives 21. The aroylhydrazones were also condensatively cyclized by heating with acetic anhydride to give the 1,3,4‐oxadiazoline derivatives 24. Structures assigned to the prepared compounds were corroborated by studying their chemical as well as their spectral characteristics.

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Selective cyclisation of 2, 3, 4, 5‐tetra‐O‐acetyl‐galactaric acid bis‐[Alkylthio(thiocarbonyl)]hydrazide to Saccharide 1, 3, 4‐Oxadiazole, Thiadiazole, and thiadiazoline derivatives

Mansour

Kassem

Abass

et al. 1991

J. Prakt. Chem.

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The synthesis of galactaric acid acetate bis[alkylthio(thiocarbonyl)]hydrazide (1, 2) is described. Selective cyclisation of both hydrazides 1 and 2 was investigated. Phosphorous oxychloride as cyclising agent led to dehydrative cyclisation and produced 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or — benzyl) 1, 3, 4‐thiadiazol‐2‐yl galactotetritol (3) or (4). While thionyl chloride led to dehydrosulfurization and gave 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or ‐benzyl)‐1, 3, 4‐oxadiazol‐2‐yl galactotetritol (5) or (6). Finally with triethyl orthoformate as cyclising agent, compounds 1 or 2, gave 3, 3′‐(2, 3, 4, 5‐tetra‐O‐acetyl‐galactar‐1.6 dioyl)bis[2‐ethoxy‐2, 3‐dihydro‐5‐S‐methyl or benzyl 1, 3, 4‐thiadiazole] (7) or (8).

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Sugar 1,3,4-Oxadiazoles. Iv: The Synthesis of Sugar 1,3,4-Oxadiazoline Derivatives

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ChemInform Abstract: SUGAR 1,3,4‐OXADIAZOLES. IV‐ THE SYNTHESIS OF SUGAR 1,3,4‐OXADIAZOLINE DERIVATIVES

ChemInform Abstract: SUGAR 1,3,4‐OXADIAZOLES. IV‐ THE SYNTHESIS OF SUGAR 1,3,4‐OXADIAZOLINE DERIVATIVES

Reactions of Aroylhydrazones, IV: Synthesis of Nitrogen Heterocycles from Opianic Acid Hydrazones

Selective cyclisation of 2, 3, 4, 5‐tetra‐O‐acetyl‐galactaric acid bis‐[Alkylthio(thiocarbonyl)]hydrazide to Saccharide 1, 3, 4‐Oxadiazole, Thiadiazole, and thiadiazoline derivatives

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