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24 February 2004

Synthesis of (3,4-bis{[2-hydroxy-3-methoxy-5-(4-methylphenyl azo)benzylidene]-amino}phenyl) phenyl methanone as a novel azo Schiff base

and
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
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Molbank2004, 2004(1), M376;https://doi.org/10.3390/M376
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Schiff bases are used as substrates in the preparation of a large of bioactive and industrial compounds via ring closure, cycloaddition, replacement reactions, etc [1] . In additon, Schiff bases are well known to have biological activites such as antibacterial [2,3,4,5], antifungal [4,5,6], antitumor [7,8,9], and herbicidal activities [10]. Also Schiff bases are used as ligands for complexation of some metal ion 11]. Azo compounds are widely used as dyes and pigments [12]. Another area of application of aromatic azo compounds is analytical chemistry where some of these compounds are used as indicators in pH, redox or complexometric titrations [13,14]. On the other hand azo compounds show biological activities containing antibacterial [15,16], pesticidal [10] activities. According to above facts, we decided to synthesize a new azo Schiff base 3 as potential biological and complexometric agent . Its biological activities and its uses in analytical works are under study.
Molbank 2004 m376 i001
Azo aldehyde 2 was synthesized according to a reported method [17]. To a stirred solution of azo aldehyde 2 (1.08 g, 3.76 mmol ) in dry CH2Cl2 (30.00 mL) at 0 oC were successively added (3,4-diaminophenyl)phenyl methanone 1(0.40 g, 1.88 mmol) and a excces of anhydrous MgSO4 (2.00 g,16.67 mmol) . The resulting mixture was stirred for 6 hours at room temperature [18]. The mixture was filtered and washed with dichloromethane . Then the solvent was evaporated under reduced pressure to give azo Schiff base 3 as a red solid which was recrystalized from ethanol 95% (1.28 g, 91 %)
m.p. 140-142 oC.
IR (KBr) (cm-1): 1604.7 (C=N), 1658.9 (C=O), 3155.3-3649.1 (OH) .
1H-NMR (CDCl3) (250 MHz) δ(ppm): 3.91 (2 OMe, s, 6H), 3.98 (2 OMe, s, 6H ) 6.89-7.01 (C6H5COC6H3, m, 8H), 7.24-7.85 (MeOC6H4N2C6H2(OH)(OMe), m, 12H), 8.70 (2HC=N, s, 2H), 13.89 (2OH, br, 2H) .
13C- NMR (CDCl3) (62.90 MHz) δ(ppm): 56.43, 56.55, 105.73, 114.40, 114.73, 114.13, 118.67, 122.41, 123.13, 124.67, 127.82, 128.65, 130.37, 132.16, 132.40, 133.65, 138.86, 146.00, 147.10, 149.54, 154.23
MS (m/z, %): 492 (C6H5COC6H3N=CC6H3OHOMeN=CC6H3OHOMeN, 3.6), 478 (C6H5COC6H3 (N=CC6H3OHOMe)2, 31.9),464 (C6H5COC6H3N=CC6H3OHOMeN=NC6H4OMe, 2.2),343 (C6H5COC6H3N=CC6H3OHOMeN, 11.8), 135 (MeOC6H4N=N, 10.7), 108 (MeOC6H5, 100.0), 105 (C6H5CO, 42.3), 77 (C6H5, 71.8) .

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Shiraz University Research council for financial support (Grant No. 81-SC-1540-C220).

References

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