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(d, 2H, J ¼ 8.4 Hz, benzyl), 7.10 (d, 1H, J ¼ 9 Hz, benzyl); IR (KBr)
nmax (cmꢁ1); 3102, 2840, 1664, 1608, 1577, 1526, 1478, 1286,
1171, 1143, 1102, 906, 855, 751, 719, 687, 578, 452. ESI-MS of 3a
at m/z ¼ 271.0 (calculated) and 271.9 (observed).
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The synthesis of 2-hydroxy-5-(4-methoxyphenyl)-azo-
benzaldehyde (3b)
1
Yield 70% H NMR (CDCl3): 11.26 (s, 1H, CHO), 10.013 (s, 1H,
OH), 8.145 (s, 1H, benzyl), 7.90 (d, 1H, J ¼ 6 Hz, benzyl), 7.11
(d, 1H, J ¼ 8.7 Hz, benzyl), 7.02 (d, 1H, J ¼ 7.8 Hz, benzyl), 3.89
(s, 3H, OCH3); IR (KBr) nmax (cmꢁ1); 3422, 2837, 1648, 1600,
1580, 1500, 1481, 1325, 1278, 1246, 1149, 1105, 1034, 838, 774,
692, 583, 506, 454. ESI-MS of 3b at m/z ¼ 256.0 (calculated) and
257.8 (3b + H+, observed).
The synthesis of compound 3a with lysine
To a solution of compound 3a (138 mg, 1.0 mmol) in ethanol
(5 ml) containing NaOH (80 mg, 2.0 mmol), lysine (146 mg,
1.0 mmol) was added and the reaction mixture was reuxed for
2 h (monitored on TLC). The precipitate so obtained was
ltered, washed with water and dried in air. Yield ¼ 72%. Mp >
200 ꢃC. 1H NMR (CDCl3) d (ppm): 10.6 (s, 1H, OH), 8.96 (s, 1H,
aldimine), 8.17 (d, 1H, J ¼ 8.4 Hz, benzyl), 7.47 (t, 2H, J ¼ 12.3,
benzyl), 7.0 (m, 2H, benzyl), 6.63 (s, 2H, NH2), 5.11 (s, 1H, –CH),
4.97 (d, 2H, J ¼ 0.3 Hz, CH2), 4.73(d, 1H, J ¼ 8.1 Hz, CH2),
4.31(m, 2H, CH2); IR (KBr) nmax (cmꢁ1); 3418, 2928, 1597, 1507,
1389, 1250, 1148, 830. ESI-MS of 3a-Lys at m/z ¼ 399.0 (calcu-
lated) and 423.1 (3a + Lys + Na+ + H+, observed).
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The synthesis of compound 3a with cysteine
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To a solution of compound 3a (138 mg, 1.0 mmol) in ethanol
(5 ml), cysteine (121 mg, 1.0 mmol) was added and the reaction
mixture was reuxed for 2–3 h. The precipitate so obtained was
ltered, washed with water and ethanol and dried in air. Yield ¼
70%. Mp > 200 ꢃC. 1H NMR (CDCl3) d (ppm): 8.59 (s, 1H, benzyl),
8.47 (s, 1H, benzyl), 8.37 (d, 1H, J ¼ 8.1, benzyl), 8.25 (s, 1H, NH),
8.19 (s, 1H, OH), 8.11 (d, 2H, J ¼ 8.4 Hz), 8.0 (d, 2H, J ¼ 6 Hz,
benzyl), 7.25 (d, 2H, J ¼ 9 Hz, benzyl), 6.18 (s, 1H, CH), 6.05
(d, 1H, J ¼ 14.1 Hz, –CH), 4.17 (s, 2H, CH2); IR (KBr) nmax (cmꢁ1);
3422, 2926, 1518, 1403, 1277, 1088, 855. ESI-MS of 3a-Cys at m/z
¼ 374.0 (calculated) and 430.1 (3a + Cys + Na+ + H+, observed).
Acknowledgements
The authors are thankful to the Council of Scientic and
Industrial Research (CSIR), New Delhi, India, for nancial
support and senior research fellowships (to SSR, RA, PS
and MS).
15 M. Zhang, M. Li, Q. Zhao, F. Li, D. Zhang, J. Zhang, T. Yi and
C. Huang, Tetrahedron Lett., 2007, 48, 2329–2333.
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17006 | RSC Adv., 2014, 4, 16999–17007
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