New hydrogen bond assisted synthesis of calixarene quinone-hydrazones

A new aci-quinone compound, 4-(aci-nitro)-2-(methoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5dienone (2), an analog to 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5-dienone (1), was successfully synthesized and fully characterized by spectroscopic methods. The reactions of 1 and 2 with various reagents such as hydroxylamine, acetic anhydride, semicarbazide and thiosemicarbazide were examined. The structure of 11 obtained new compounds was established by IR, 1 H NMR, 13 C NMR, HMBC and MS spectra. It was shown that the unstable, sensitive aci-quinone structure of compounds 1 and 2 can exist in anhydrous organic solvents such as AcOEt, EtOH but in the presence of water, H + , HOor at high temperatures, the aci-quinone structure of both 1 and 2 tendentiously transformed into the more stable nitro-phenol form.

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New hydrogen bond assisted synthesis of calixarene quinone-hydrazones

Abstract: The hydrogen bond assisted synthesis of calix[n]arene quinone-hydrazones(II) has been achieved through coupling octahydroxycalix[8]arenes with solutions of diazotized 2-amino benzoic acid and 4-nitrophenyl-2-aminobenzoate in pyridine.

Cited by 2 publications

References 4 publications

Synthesis of novel chromogenic azocalix[4]arenemonoquinones and their binding with alkali metal cations

Synthesis of novel chromogenic azocalix[4]arenemonoquinones and their binding with alkali metal cations

Aci-Quinone Compounds from Eugenoxyacetic Acid and Methyleugenol: Preparation and Reaction

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