ORIGINAL ARTICLE
Year : 2012  |  Volume : 11  |  Issue : 2  |  Page : 129-135

Synthesis of triazole, pyrazole, oxadiazine, oxadiazole, and sugar hydrazone-5-nitroindolin-2-one derivatives ( part I)


1 Department of Chemistry of Natural and Microbial Products; Pharmaceutical Research Group, Center of Excellence for Advanced Sciences, National Research Center Dokki, Cairo, Egypt
2 Department of Chemistry of Natural and Microbial Products, Center of Excellence for Advanced Sciences, National Research Center Dokki, Cairo, Egypt
3 Department of Plant Pathology and Safe of Agriculture group, Center of Excellence for Advanced Sciences, National Research Center Dokki, Cairo, Egypt
4 Department of Pharmacology, Theodor Bilharz Research Institute, Giza, Egypt
5 Atomic and Molecular Physics Unit, Department of Nuclear Physics. Atomic Energy Authority, Cairo, Egypt
6 Department of Analytical Chemistry, Stockholm University, Stockholm, Sweden

Correspondence Address:
Fatma A. Bassyouni
PhD, Department Chemistry of Natural and Microbial Products, Center of Excellence for Advanced Sciences, National Research Centre, 12622, Cairo
Egypt
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Source of Support: None, Conflict of Interest: None


DOI: 10.7123/01.EPJ.0000422115.68888.f2

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Objective

The aim of part I is the synthesis of different series of 1H-1,2,4-triazol-3-yl)phenylimino)(methylbenzyl)-5-nitroindolin-2-ones, 1H-pyrazole-1-carbonyl)phenylimino)-1-(p-methylbenzyl)-5-nitroindolin-2-ones, 3-(4-(1,3,4-oxadiazin-6-one)phenylimino)-1-(p-methylbenzyl)-5-nitroindolin-2-ones, 1,3,4-oxadiazol-2-yl)phenylimino)-1-(p-methylbenzyl)-5-nitroindolin-2-ones, and 4-(-1-(p-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino) sugar hydrazone derivatives (4–13) through the reaction of 4-[1-(p-methylbenzyl)-5-nitro-2-oxoindolin-3-ylidineamino]benzohydrazide (3) with different reagents to be evaluated biologically.

Materials and methods

Derivatives of (1H-1,2,4-triazol-3-yl)phenylimino)-1-(p-methylbenzyl)-5-nitroindolin-2-one and (1H-pyrazole-1-carbonyl)phenylimino)-1-(p-methylbenzyl)-5-nitroindolin-2-one (4–6) were prepared by the reaction of 4-[(1-(p-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino)] benzohydrazide (3) with benzyl, benzoyl isothiocyanate, or acetyl acetone to form 1H-1,2,4-triazole and 1H-pyrazole-5-nitroindolin-2-one derivatives. The reaction of 3 with ethyl bromoacetate, ethyl acetoacetate, or acetyl chloride afforded 1,3,4 oxadiazin-6-one, 3-methyl-5-oxo-4,5-dihydro-1H-pyrazole, or 1,3,4-oxadiazole-5-nitroindolin-2-one derivatives (7–9), respectively. Sugar hydrazone-5-nitroindolin-2-ones (10–13) were archived by the reaction of 3 with D-glucose, D-mannose, D-arabinose, and D-ribose using both conventional and green chemistry.

Results and conclusion

Conventional and microwave methods used for the synthesis of various triazole, pyrazole, oxadiazine, oxadiazole, and sugar hydrazone-5-nitroindolin-2-one derivatives were applied for the synthesis of compounds 4–13. These methods were simple and gave good yields of the target compounds in short reaction times.



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