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

Bassyouni, Fatma A.; Abdel All, Amira S.; Haggag, Wafaa M.; Mahmoud, Madiha; Sarhan, Mamoun M.A.; Abdel-Rehim, Mohamed

doi:10.7123/01.EPJ.0000422115.68888.f2

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

Authors

10.7123/01.EPJ.0000422115.68888.f2

Abstract

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-(-methylbenzyl)-5-nitroindolin-2-ones, 3-(4-(1,3,4-oxadiazin-6-one)phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-ones, 1,3,4-oxadiazol-2-yl)phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-ones, and 4-(-1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino) sugar hydrazone derivatives ( through the reaction of 4-[1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylidineamino]benzohydrazide () 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 () were prepared by the reaction of 4-[(1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino)] benzohydrazide () 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 with ethyl bromoacetate, ethyl acetoacetate, or acetyl chloride afforded 1,3,4 oxadiazin-6-one, 3-methyl-5-oxo-4,5-dihydro-1-pyrazole, or 1,3,4-oxadiazole-5-nitroindolin-2-one derivatives (), respectively. Sugar hydrazone-5-nitroindolin-2-ones () were archived by the reaction of 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 . These methods were simple and gave good yields of the target compounds in short reaction times.

Keywords