Synthesis  of novel azo Schiff base bis[5-(4-methoxyphenylazo)-2-hydroxy -3-methoxy benzaldehyde]-1,2-phenylene diimine

A. A. jarrahpour*, M. Zarei

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran Tel.  0098 711 2284822,  Fax: 0098 711 2280926

E-mail: [email protected],  [email protected]

Received: 16 January 2004 / Accepted: 23 February 2004 / Published: 24 February 2004 

Keywords : Schiff base, biological activity, 1,2-phenylene diamine, azo aldehyde, dyes .

Schiff bases are a class of important compounds  in medicinal  and  pharmaceutical field. They    show  biological  activities  including  antibacterial [1-4], antifungal [5-6], anticancer [7-9],   and herbicidal [10]  activities . Furthermore,  Schiff  bases  are utilized as  starting  material  in  the synthesis of industrial[11] and biological compounds  such as β-lactams[12],  etc. Azo compounds  have been used for a long time  as dyes  in industry [13].  In addition, azo compounds are used in analytical chemistry as indicators in pH, redox, or complexometric titrations [14-15]. Some azo compouns have shown a good antibacterial activity 16-17]. The existence of an azo moiety in different types of  compounds has  caused them to show pesticidal activity [10]. Based on the mentioned properties for Schiff bases and azo compounds, we decided to synthesize a novel azo Schiff base 3. The biological and analytical uses of 3 are under study.

Azo aldehyde 2  was  synthesized according to a reported  method[18]. A  mixture of  1,2-phenylene diamine 1 (0.50 g, 4.62 mmol) and  2-hydroxy-3-methoxy-5 (4-methoxyphenylazo) benzaldehyde 2 (2.65 g, 9.26 mmol) in absolute ethanol (40.00 mL) was  refluxed for 3 hours  to give a dark red  precipitate. Then  it  was filtered and  washed with ethanol  to give  pure azo Schiff base 3  (2.92 g, 98 % ).

m.p. 185-187 ^oC.

IR (KBr) (cm^-1): 1604.70 (HC=N), 3163.00-3672.20 (OH) .   

,¹H-NMR (CDCl ₃) (250 MHz) (ppm): 3.86  (2 OMe, s, 6H), 3.94 (2 OMe, s, 6H), 6.97-7.01(C₆H₄N₂, m, 4H), 7.26-7.62 (2N₂C₆H₄OMe, m, 8H), 7.85-7.89 (2HOC₆H₂OMe, m, 4H), 8.66 (2HC=N, s, 2H), 13.94 (2 OH, br, 2H) .  

,¹³C- NMR (CDCl ₃ ) (62.90 MHz) (ppm): 55.93, 56.31, 105.45, 114.59, 120.07, 123.75, 124.76, 125.01, 128.39, 141.10, 145.10, 147.20, 150.12, 156.85, 163.26

MS (m/z,  %): 388 (HOMeOC₆H₂C=NC₆H₄N=CC₆H₂OHOMeN, 2.6), 374 (C₆H₄(N=CC₆H₂ OHOMe)₂, 55.3), 360 (C₆H₄N=CC₆H₂OHOMeN=NC₆H₄OMe, 2.3), 239 (C₆H₄N=CC₆H₂OHOMeN, 21.4), 225 (C₆H₄N=CC₆H₂OHOMe, 2.6), 135 (MeOC₆H₄N=N, 28.8), 107 (MeOC₆H₄, 100.0) .

Acknowledgment

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

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