2013
DOI: 10.4067/s0717-97072013000200027
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Synthesis, Crystal Structures and Antibacterial Activities of Benzohydrazone Derivatives From 4-Diethylaminosalicylaldehyde

Abstract: A series of three new benzohydrazone compounds, C 18 H 21 N 3 O 3 (1), C 19 H 23 N 3 O 3 (2), and C 18 H 20 ClN 3 O 2 (3), derived from the condensation of 4-diethylaminosalicylaldehyde with 2-hydroxybenzohydrazide, 4-methoxybenzohydrazide, and 4-chlorobenzohydrazide, respectively, in methanol, were prepared. The compounds were characterized by elemental analysis, IR spectra, 1 H NMR spectra, and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group

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Cited by 5 publications
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“…Synthesis of ­ N ′‐(4‐diethylamino‐2‐hydroxybenzylidene)‐2‐hydroxybenzohydrazide (1) : A solution of 2‐hydroxybenzohydrazide ( 3 ) (1.52 g, 10 mmol), 4‐(diethylamino)salicylaldehyde ( 2 ) (1.93 g, 10 mmol), and piperidine (0.50 mL) in EtOH (25 mL) was heated at reflux for 4 h. The resulting yellow precipitate was isolated by filtration and then washed with EtOH to give the crude product. Purification by column chromatography (hexane/EtOAc, 2:1→1:1) gave the title compound as a pale yellow solid (2.77 g, 81 % yield): 1 H NMR (500 MHz, [D 6 ]DMSO): δ =8.48 (s, 1 H), 7.87 (d, J =6.5 Hz, 1 H), 7.44–7.42 (m, 1 H), 7.29 (d, J =8.5 Hz, 1 H), 6.97–6.93 (m, 2 H), 6.38 (d, J =8.5 Hz, 1 H), 6.24 (s, 1 H), 3.38 (q, J =7.0 Hz, 4 H), 1.09 ppm (t, J =7.0 Hz, 6 H); 13 C NMR (125 MHz, [D 6 ]DMSO): δ =165.0, 159.8, 159.6, 150.2, 134.5, 132.1, 129.2, 119.5, 117.8, 116.0, 48.5, 11.7 ppm; MS (ESI): m/z =327 [ M ] + .…”
Section: Methodsmentioning
confidence: 99%
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“…Synthesis of ­ N ′‐(4‐diethylamino‐2‐hydroxybenzylidene)‐2‐hydroxybenzohydrazide (1) : A solution of 2‐hydroxybenzohydrazide ( 3 ) (1.52 g, 10 mmol), 4‐(diethylamino)salicylaldehyde ( 2 ) (1.93 g, 10 mmol), and piperidine (0.50 mL) in EtOH (25 mL) was heated at reflux for 4 h. The resulting yellow precipitate was isolated by filtration and then washed with EtOH to give the crude product. Purification by column chromatography (hexane/EtOAc, 2:1→1:1) gave the title compound as a pale yellow solid (2.77 g, 81 % yield): 1 H NMR (500 MHz, [D 6 ]DMSO): δ =8.48 (s, 1 H), 7.87 (d, J =6.5 Hz, 1 H), 7.44–7.42 (m, 1 H), 7.29 (d, J =8.5 Hz, 1 H), 6.97–6.93 (m, 2 H), 6.38 (d, J =8.5 Hz, 1 H), 6.24 (s, 1 H), 3.38 (q, J =7.0 Hz, 4 H), 1.09 ppm (t, J =7.0 Hz, 6 H); 13 C NMR (125 MHz, [D 6 ]DMSO): δ =165.0, 159.8, 159.6, 150.2, 134.5, 132.1, 129.2, 119.5, 117.8, 116.0, 48.5, 11.7 ppm; MS (ESI): m/z =327 [ M ] + .…”
Section: Methodsmentioning
confidence: 99%
“…Synthesis of N'-(4-diethylamino-2-hydroxybenzylidene)-2-hydroxybenzohydrazide (1): [34] As olution of 2-hydroxybenzohydrazide (3)( 1.52 g, 10 mmol), 4-(diethylamino)salicylaldehyde (2) (1.93 g, 10 mmol), and piperidine (0.50 mL) in EtOH (25 mL) was heated at reflux for 4h.T he resulting yellow precipitate was isolated by filtration and then washed with EtOH to give the crude product. Purification by column chromatography (hexane/EtOAc, 2:1!1:1) gave the title compound as ap ale yellow solid (2.77 g, Fluorometric and UV-vis titrations:S olutions (5.0 mm)o fK + , Co 2 + ,C a 2 + ,B a 2 + ,N i 2 + ,P b 2 + ,H g 2 + ,C e 2 + ,Z n 2 + ,C d 2 + ,F e 3 + ,a nd Al 3 + in CH 3 CN/H 2 O( 1:1 v/v)w ere prepared from the chloride or ni- www.chemistryopen.org trate salt.…”
Section: Methodsmentioning
confidence: 99%
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“…The activity of complex was better against the S. aureus from the laboratory private patient than against the ATCC 25923 one. Bellú Recently, it has been reported the antibacterial activity of benzohydrazone derivatives against Escherichia coli, Staphylococcus aureus, and Klebsiella pneumonia and the results indicate that the compounds show moderate activities against the growth of the tested strains 33 . …”
Section: Antimicrobial Activitymentioning
confidence: 99%