Synthesis and elucidation of structure of hydrazones derived from N-(2,4-dimethylphenyl)-3-oxobutanamide

Hamzaçebi, Murat Çağlar; Rollas, Sevim; Küçükgüzel, Ş. Güniz; Kaymakçıoğlu, Bedia Koçyiğit

doi:10.3998/ark.5550190.0009.c20

Cited by 5 publications

(3 citation statements)

References 18 publications

(20 reference statements)

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“…The structures of the products were established on the basis of their elemental analyses and spectral data (IR, 1 H NMR, and MS) [see Experimental Part]. In the 1 H NMR spectra of compounds 3a – e , absence of signal assignable to azomethine group (CH–N=N–) [ 37 ] at δ 3.00–4.00 ppm ruled out azo form and supported the hydrazone structure of the products.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis and Antimicrobial Evaluation of Some New Heterocyclic Compounds Incorporating a Biologically Active Sulfamoyl Moiety

Darwish

2014

The Scientific World Journal

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A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reacted in situ with chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, ketene N,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.

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Section: Resultsmentioning

confidence: 99%

Facile Synthesis and Antimicrobial Evaluation of Some New Heterocyclic Compounds Incorporating a Biologically Active Sulfamoyl Moiety

Darwish

2014

The Scientific World Journal

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“…Several studies were reported for the biological activities of hydrazide-hydrazone structures [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. The hydrazone group has an advantage of blocking the free amine for metabolic stability.…”

Section: Biological Activitymentioning

confidence: 99%

Synthesis, Structure Elucidation and Biological Activity of New Hybrid Hydrazone-Amide Compounds

Coşkun

AKLAMUZ

İnce

et al. 2022

Cumhuriyet Science Journal

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Bacterial infection today occupies a tremendous place in world health. The infection diseases were kept under control after the development of penicillin and further studies were performed on the development of new antibacterial agents. However, to date, bacterial resistance caused a big failure in the treatment of infectious disease and therefore, development of new antibacterial agents became important for human health. In the present study, we have designed, synthesized and elucidated the structures of new hydrazide-hydrazone compounds and their hybrid amide derivatives. The structures of the compounds were elucidated with spectroscopic methods and their purity were proven by TLC, HPLC-MS analysis. The antibacterial and antifungal activity studies of the novel molecules were investigated on different strains. Among the synthesized compounds, AA3a and AA4a appeared to show promising antibacterial activity. None of the compounds showed significant antifungal activity on Candida albicans. The drug likeness properties and boiled-egg plot analysis were performed for all of the compounds. The novel molecules showed no violation on Lipinski’s rule of five and all the molecules showed good gastrointestinal absorption properties in the in silico studies.

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“…It can be used to prepare azobenzene derivatives with active functional 86 ZANCO Journal of Pure and Applied Sciences 2023 groups as a precursor for further synthesis to give Azo-amide. (Hamzacebi et al, 2008), Azoimine (Ziarani et al, 2018) and Azo-chalcone (Al-Asiri, 2000) Synthetic colors are widely used in many modern sectors, including textiles, leather, paper, and the creation of food and hair coloring. Because of delocalization, the most popular synthetic Azo dyes used for dyeing fabrics and textiles were generally highly colored, i.e.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and dye performance investigations of azo-coumarin bearing chalcone moieties

2023

ZJPAS

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The preparation of several azo dyes(2a-h) involved the reaction of 4-aminoacetophenone with sodium nitrite to produce the corresponding diazonium salts, which were then permitted to react with 4-Hydroxycoumarin to produce the relevant azo dye (A). The prepared starting material (A) was then reacted with various substituted benzaldehydes to give a new series of chalcone derivatives(2a-h). Additionally, FT-IR and 1H-NMR spectra used to validate the structures of the newly synthesized compounds. Acid and dispersion dyes are employed with all azo compounds to execute dyeing on multi-fiber strips made of acetate, cotton, nylon, wool, acrylic, and polyester fibers. Each fiber was given moderate to exceptional fastness characteristics by all the synthetic dyes.

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Synthesis and elucidation of structure of hydrazones derived from N-(2,4-dimethylphenyl)-3-oxobutanamide

Abstract: Diazonium salts derived from amines 1 (sulfanilic acid, 4-nitroaniline, 4-aminosalicylic acid, sulfanilamide, sulfamethoxazole, sulfathiazole, sulfapyridine, sulfamerazine) were coupled with N-(2,4-dimethylphenyl)-3-oxobutanamide (2) resulting in the formation of hydrazones 3a-h.

Cited by 5 publications

References 18 publications

Facile Synthesis and Antimicrobial Evaluation of Some New Heterocyclic Compounds Incorporating a Biologically Active Sulfamoyl Moiety

Facile Synthesis and Antimicrobial Evaluation of Some New Heterocyclic Compounds Incorporating a Biologically Active Sulfamoyl Moiety

Synthesis, Structure Elucidation and Biological Activity of New Hybrid Hydrazone-Amide Compounds

Synthesis, characterization, and dye performance investigations of azo-coumarin bearing chalcone moieties

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