Novel and selective synthesis of unsymmetrical azine derivatives via a mild reaction

Safari, Javad; Gandomi‐Ravandi, Soheila; Monemi, Mohammad

doi:10.1007/s00706-013-0945-3

Cited by 19 publications

(9 citation statements)

References 13 publications

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“…These are prepared in two steps as described in the set of works reported in the literature, from two different aromatic derivatives aldehyde or ketone, and hydrazine hydrate [34][35] or selectively using hydrazine derivatives [36][37]. In our case, we have drawn from the work reported in the literature [38] which indicates the possibility of preparing unsymmetrical azines in a single step by reacting two different carbonyl derivatives simultaneously with hydrazine sulfate in the presence of a base in molecular proportions: 1/1/1, without worrying about the difference in reactivity between the C=O groups. We then borrowed this new method which proves efficient and practical, on which we made a minor modification of the reaction conditions as indicated in the experimental part.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Yahyaoui

Bouchama²,

Anak³

et al. 2019

Journal of Molecular Structure

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In this paper, we report the synthesis of new unsymmetrical azines Schiff bases. These compounds were prepared by condensation of hydrazine with different aldehydes and ketones to give (E) -2-hydroxynaphthalene-1-carbaldehyde [(1E) -2-thienylmethylene] hydrazone compound (I) and (Z) -2 -[(E) -1-(2-hydroxyphenyl) ethylidenehydrazin-1-ylidene] -1,2diphenylethanone compound (II). The method adopted consists in reacting the two different carbonyl compounds simultaneously in one step in a stepwise manner reported which is practical and cost-effective. The reaction with a minor modification in operating conditions proceeded efficiently and with excellent performance. The structure of each of the two compounds (I) and (II) was determined by the X-ray diffraction technique performed on single crystals. The asymmetric unity of the two molecules consists of one asymmetry-independent molecule. In addition, hydrogen bonds C-H ... π are observed in the compound (II). We then present a detailed DFT study based on B3LYP / 6-31G (d, p) geometric structures of compounds (I); (II) and another compound (III) also another asymmetric azine (Z) -2 -[(E) -2-benzylidenehydrazine-1-ylidene] -1,2diphenylethanone whose crystal structure is reported. The fundamental vibration wave numbers are calculated and a good agreement between the observed and calculated wave numbers is obtained. The study was extended to the HOMO-LUMO analysis to calculate the energy gap. The calculated HOMO and LUMO energy reveals that the charge is transferred into the molecule.

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Section: Introductionmentioning

confidence: 99%

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Yahyaoui

Bouchama²,

Anak³

et al. 2019

Journal of Molecular Structure

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“…The compounds structurally similar to the ones reported in this paper have already been described in literature [19][20][21][22][23]. However, their electrochemical and photovoltaic properties have not been investigated and described.…”

Section: Introductionmentioning

confidence: 53%

“…Isomer of azine in our work denoted as BTD (synthesized from 2-thiophenealdehyde) have been prepared using benzophenone hydrazone and 3-bromothiophene-2-carboxaldehyde [22]. Moreover, a new, selective and mild synthesis of unsymmetrical azines from aromatic aldehydes and hydrazine sulfate in triethylamine has been reported recently [23]. This paper presents a comprehensive study of obtained azines; their physical properties such as thermal (DSC), optical (UV-Vis), and electrochemical (CV and DPV) were investigated and discussed in relation to their chemical structure.…”

Section: Introductionmentioning

confidence: 99%

Unsymmetrical and symmetrical azines toward application in organic photovoltaic

et al. 2015

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“…However symmetrical azines readily synthesize, starting with excess aldehyde or ketone (41,42). On the other hand, novel and selective methods for the synthesis of azines have been reported (43). So, in this work, we used semicarbazide HCl in an acidic medium to forward the reaction from the general intermediate, Imp-C, to obtain the required compound, Imp-D, which was produced with good yield.…”

Section: Methods Developments and Optimizationmentioning

confidence: 99%

Quantitative Determination of Synthesized Genotoxic Impurities in Nifuroxazide Capsules by Validated Chromatographic Methods

et al. 2018

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Two accurate, selective, and precise chromatographic methods, namely TLC-densitometric and reversed-phase (RP)-HPLC, were developed and validated for the simultaneous determination of nifuroxazide (NIF) and its four synthesized impurities, which are also reported to be its related substances in the range of 10-100 μg/band and 10-100 μg/mL for NIF in the TLC and RP-HPLC methods, respectively. The developed TLC-densitometric method depended on the separation and quantitation of the studied components on silica gel 60 F254 TLC plates. Ethyl acetate-acetone-methanol-ammonia (85 + 25 + 5 + 0.5, v/v/v/v) was used as the developing system, and the separated bands were UV-scanned at 230 nm. On the other hand, the developed RP-HPLC method depended on chromatographic separation using a C8 column at 25°C and an aqueous solution of 0.1% sodium lauryl sulfate-acetonitrile as the mobile phase delivered according to the gradient elution program. Factors affecting the developed methods were studied and optimized. Also, method validation was carried out according to International Conference on Harmonization guidelines. The proposed methods were successfully applied for the determination of the studied drug in its bulk powder and in its pharmaceutical formulation. The developed methods showed no significant difference when compared with the reported RP-HPLC one. Their advantage is being the first stability-indicating methods for NIF and its genotoxic impurities.

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Novel and selective synthesis of unsymmetrical azine derivatives via a mild reaction

Cited by 19 publications

References 13 publications

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Unsymmetrical and symmetrical azines toward application in organic photovoltaic

Quantitative Determination of Synthesized Genotoxic Impurities in Nifuroxazide Capsules by Validated Chromatographic Methods

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