In this work new heterocyclic pyrazolin derivatives have been synthesized from diazonium chloride salt of 4-aminobenzoic acid: firstly, Azo compounds were prepared from the reaction of an ethanolic solution of sodium acetate and calculated amount of active methylene compound namely, (ethyl acetoacetate)obtain the corresponding hydrazono derivative (1). Secondly, Cyclocondensation reaction of compound (1) with hydrazine hydrate (2) in boiling ethanol affording the corresponding pyrazoline-5-one. Then compound (2) reacted with thionyl chloride to give the corresponding acid chloride derivative(3), followed by conversion into the corresponding carboxylic acid thiosemicarbazide (4), esters (7-9), thioesters (10), (11), and amides (12-14), when treated hydrazine hydrate, thiosemicarbazide, alcohols, alkylthiol and secondary amines in dry refluxing benzene; respectively. Furthermore, 1,2,4- triazole heterocyclic ring, which might result in biologically active agents, have been prepared by refluxing thiosemicarbazide derivative (4) with sodium hydroxide solution (4%) followed acidification of the result using (10%)HCl solution. Moreover, 1, 3, 4, - thiadiazole heterocyclic ring (6) has been prepared by treatment of thiosemicarbazide derivative with concentrated sulfuric acid as cyclization agent. Finally, derivative (15) has prepared by reflux (1) with phydroxybenzaldehydethen the product reflux with 5-amino-1, 3, 4-thiadiazol-2- thiol to product (16) derivative. All structures of newly synthesized compounds have been characterized and identified via of their physical properties and spectral data analysis (IR, UV.)
This work describes the synthesis of a new fructofuranosyl derivatives comprising 1,2,3triazole, 1,2,3-triazoline or tetrazole rings via 1,3-dipolar cycloaddition reaction. To obtain these derivatives, 1,3,4,6-tetra-O-benzoyl--D-fructofuranose (1) with free hydroxyl group at position-2 was prepared as the starting material. Reaction of compound (1) with 45% HBr solution in glacial acetic acid gave compound (2). The bromide (2) was then made to react with some nucleophiles (NaN 3 and KCN) to give 1,3,4,6-tetra-O-benzoyl--D-fructofuranosyl azide (3) and 1,3,4,6-tetra-O-benzoyl--D-fructofuranosyl cyanide (4). Treatment of compound (3) with cinnamic acid, cinnamaldehyde, acrylic acid, acrylonitrile, acrylamide and maleic anhydride, gave the triazoline derivatives (5-10). Cycloaddition reaction was also carried out with propargyl chloride, propargyl alcohol and 1-hexyn-3-ol using (ph 3 P) 3 CuI as a catalyst to give the triazole derivatives (12-14). Reaction of the cyanosugar (4) with arylsulfonyl azides gave the tetrazole derivatives (16-18). Antibacterial and antifungal activities of some novel synthesized compounds were studied and compared with that of two well known antibiotics (Ampicillin and Gentamycin).
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