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Cyclization of 2,3,4,5-tetra-O-acetylgalactaric bis-(aroylhydrazides) to saccharide bis(1,3,4-oxadiazolyl) derivatives

✍ Scribed by Mahmoud A.M. Nassr; Mamdouh A.M. Taha; Mohammed A.E. Shaban


Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
478 KB
Volume
121
Category
Article
ISSN
0008-6215

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✦ Synopsis


Condensation of 2,3,4,S-tetra-0-acetylgalactaroyl dichloride with two equivalents of various aroylhydrazines gave the corresponding 2.3,4,5-tetra-O-acetylgalactaric bis(aroylhydrazides). Condensative and dehydrativc cyclization of these bis(hydrazides) with triethyl orthoformate and phosphoryl chloride, respectively, gave the corresponding 3,3'-(2,3.4,5-tetra-O-acetylgalactar-1,6-dioyl)-bis(5-aryl-2-cthoxy-2,3-dihydro-1,3,4-oxadiazole) and 1,2,3.4-tctra-O-acetyl-1.4-bis(%aryl-1,3,4-oxadiazol-Z-yl)-gala&o-tetritols. The elucidation of the structure of the compounds prepared is discussed and mechanistic pathways for their formation are proposed.


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