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B.R. Vijay Avin et al. / European Journal of Medicinal Chemistry 75 (2014) 211e221
(KBr): 1640 (C]O), 1660 (amide, C]O), 1730 (ester, C]O), 3200e
3300 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
ester), 2.3 (s, 3H, CH3), 3.14 (s, 2H, CH2), 3.82 (s, 3H, OCH3), 4.18 (q,
C21H21ClN2O6 (432.5): C, 58.20; H, 4.85; N, 6.47. Found: C, 58.22; H,
4.87; N, 6.45%.
d
1.25 (t, J ¼ 7 Hz, 3H, CH3 of
J ¼ 6 Hz, 2H, CH2 of ester), 4.7 (s, 2H, OCH2), 6.8e7.7 (m, 7H, AreH),
4.2.3.7. (N-{2-[2-(3-bromo-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4g. Yield 65%; M.p. 220e223 ꢂC;
IR (KBr): 1645 (C]O), 1664 (amide, C]O), 1738 (ester, C]O),
9.2 (bs, 2H, NH); 13C NMR (CDCl3):
d 13.6, 20.9, 39.3, 56.0, 59.2, 78.0,
113.7, 113.8, 123.3, 129.7, 130.1, 131.1, 131.8, 133.9, 160.6, 165.7, 170.3,
171.0, 187.0. EI-MS: m/z 428 (Mþ, 48). Anal. Calcd. for C22H24N2O7
(428): C, 61.68; H, 5.6; N, 6.54. Found: C, 61.65; H, 5.4; N, 6.57%.
3208e3315 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.28 (t, J ¼ 7 Hz, 3H,
CH3 of ester), 2.29 (s, 3H, CH3), 3.13 (s, 2H, CH2), 4.17 (q, J ¼ 6 Hz, 2H,
CH2 of ester), 4.74 (s, 2H, OCH2), 6.75e7.71 (m, 7H, AreH), 9.28 (bs,
4.2.3.2. (N-{2-[2-(3-chloro-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4b. Yield 71%; M.p. 234e236 ꢂC;
IR (KBr): 1642 (C]O), 1658 (amide, C]O), 1732 (ester, C]O),
2H, NH); 13C NMR (CDCl3):
d 13.62, 20.93, 39.32, 59.22, 78.02,
113.73, 123.32, 124.7, 127.2, 129.71, 131.5, 131.81, 132.3, 133.9, 134.4,
141.1, 160.62, 170.32, 171.02, 187.03. EI-MS: m/z 477 (Mþ, 48). Anal.
Calcd. for C21H21BrN2O6 (477): C, 52.83; H, 4.40; N, 5.87. Found: C,
52.85; H, 4.43; N, 5.85%.
3210e3310 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.3 (t, J ¼ 7 Hz, 3H,
CH3 of ester), 2.31 (s, 3H, CH3), 3.15 (s, 2H, CH2), 4.18 (q, J ¼ 6 Hz, 2H,
CH2 of ester), 4.72 (s, 2H, OCH2), 6.75e7.71 (m, 7H, AreH), 9.28 (bs,
2H, NH); 13C NMR (CDCl3):
d
13.61, 20.92, 39.31, 59.21, 78.01, 113.72,
4.2.3.8. (N-{2-[2-(4-bromo-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4h. Yield 65%; M.p. 212e213 ꢂC; IR
(KBr): 1642 (C]O), 1660 (amide, C]O), 1740 (ester, C]O), 3212e
123.31, 128.2, 129.6, 129.7, 130.5, 131.8, 132.6, 133.5, 133.9, 139.2,
160.6, 170.31, 171.01, 187.02; EI-MS: m/z 432 (Mþ,48); Anal. Calcd.
for C21H21ClN2O6 (432.5): C, 58.20; H, 4.85; N, 6.47. Found: C, 58.22;
H, 4.87; N, 6.45%.
3318 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.25 (t, J ¼ 7 Hz, 3H, CH3 of
ester), 2.22 (s, 3H, CH3), 3.15 (s, 2H, CH2), 4.18 (q, J ¼ 6 Hz, 2H, CH2 of
ester), 4.74 (s, 2H, OCH2), 6.70e7.75 (m, 7H, AreH), 9.26 (bs, 2H,
4.2.3.3. (N-{2-[2-(2-bromo-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4c. Yield 69%; M.p. 225e227 ꢂC; IR
(KBr): 1644 (C]O), 1654 (amide, C]O), 1736 (ester, C]O), 3205e
NH); 13C NMR (CDCl3):
d 13.62, 20.93, 39.32, 59.22, 78.02, 113.73,
123.32, 124.7, 127.2, 129.71, 131.5, 131.81, 132.3, 133.9, 134.4, 141.1,
160.62, 170.32, 171.02, 187.03. EI-MS: m/z 477 (Mþ, 48). Anal. Calcd.
for C21H21BrN2O6 (477): C, 52.83; H, 4.40; N, 5.87. Found: C, 52.85;
H, 4.43; N, 5.85%.
3308 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.28 (t, J ¼ 7 Hz, 3H, CH3 of
ester), 2.29 (s, 3H, CH3), 3.13 (s, 2H, CH2), 4.17 (q, J ¼ 6 Hz, 2H, CH2 of
ester), 4.74 (s, 2H, OCH2), 6.75e7.71 (m, 7H, AreH), 9.28 (bs, 2H,
NH); 13C NMR (CDCl3):
d
13.62, 20.93, 39.32, 59.22, 78.02, 113.73,
4.2.3.9. (N-{2-[2-(4-fluoro-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4i. Yield 78%; M.p. 202e204 ꢂC; IR
(KBr): 1666 (C]O), 1659 (amide, C]O), 1755 (ester, C]O), 3230e
123.32, 124.7, 127.2, 129.71, 131.5, 131.81, 132.3, 133.9, 134.4, 141.1,
160.62, 170.32, 171.02, 187.03; EI-MS: m/z 477 (Mþ, 48). Anal. Calcd.
for C21H21BrN2O6 (477): C, 52.83; H, 4.40; N, 5.87. Found: C, 52.85;
H, 4.43; N, 5.85%.
3320 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.35 (t, J ¼ 7 Hz, 3H, CH3 of
ester), 2.4 (s, 3H, CH3), 3.18 (s, 2H, CH2), 4.3 (q, J ¼ 6 Hz, 2H, CH2 of
ester), 4.6 (s, 2H, OCH2), 6.9e7.6 (m, 8H, AreH), 9.3 (bs, 2H, NH); 13
NMR (CDCl3): 13.66, 20.80, 39.35, 59.25, 78.3, 113.74, 123.35,
C
4.2.3.4. (N-{2-[2-benzoyl-4-methyl-phenoxy]-acetyl}hydrazino-
carbonyl)-ethyl acetate 4d. Yield 72%; M.p. 218e220 ꢂC; IR (KBr):
1640 (C]O), 1652 (amide, C]O), 1733 (ester, C]O), 3200e
d
128.5, 129.75, 130.15, 131.85, 132.24, 133.95, 137.85, 160.65, 170.35,
171.1, 187.08. EI-MS: m/z 416 (Mþ, 48). Anal. Calcd. for C21H21FN2O6
(416): C, 60.57; H, 5.08; N, 6.73. Found: C, 60.59; H, 5.05; N, 6.77%.
3300 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.3 (t, J ¼ 7 Hz, 3H, CH3 of
ester), 2.28 (s, 3H, CH3), 3.12 (s, 2H, CH2), 4.16 (q, J ¼ 6 Hz, 2H, CH2 of
ester), 4.75 (s, 2H, OCH2), 6.76e7.75 (m, 8H, AreH), 9.1 (bs, 2H, NH);
4.2.3.10. (N-{2-[2-(4-methyl-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4j. Yield 78%; M.p. 210e212 ꢂC; IR
(KBr): 1640 (C]O), 1660 (amide, C]O), 1738 (ester, C]O), 3215e
13C NMR (CDCl3):
d 13.61, 20.92, 39.31, 59.21, 78.0, 113.71, 123.31,
128.2, 129.71, 130.1, 131.81, 132.2, 133.91, 137.8, 160.62, 170.32,
171.02, 187.02. EI-MS: m/z 398 (Mþ, 48). Anal. Calcd. for C21H22N2O6
(398): C, 63.31; H, 5.52; N, 7.03. Found: C, 63.34; H, 5.55; N, 7.05%.
3300 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
ester), 2.4 (s, 3H, CH3), 2.5 (s, 3H, CH3), 3.14 (s, 2H, CH2), 4.18 (q,
d
1.26 (t, J ¼ 7 Hz, 3H, CH3 of
J ¼ 6 Hz, 2H, CH2 of ester), 4.7 (s, 2H, OCH2), 6.9e7.8 (m, 7H, AreH),
4.2.3.5. (N-{2-[2-(2-chloro-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4e. Yield 70%; M.p. 202e204 ꢂC;
IR (KBr): 1660 (C]O), 1655 (amide, C]O), 1740 (ester, C]O),
9.5 (bs, 2H, NH); 13C NMR (CDCl3):
d 13.6, 20.9, 39.3, 56.0, 59.2, 78.0,
113.7, 113.8, 123.3, 129.7, 130.1, 131.1, 131.8, 133.9, 160.6, 165.7, 170.3,
171.0, 187.0. EI-MS: m/z 412 (Mþ, 48). Anal. Calcd. for C22H24N2O6
(412): C, 64.07; H, 5.87; N, 6.79. Found: C, 64.04; H, 5.89; N, 6.76%.
3240e3330 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.32 (t, J ¼ 7 Hz, 3H,
CH3 of ester), 2.3 (s, 3H, CH3), 3.15 (s, 2H, CH2), 4.2 (q, J ¼ 6 Hz, 2H,
CH2 of ester), 4.8 (s, 2H, OCH2), 6.8e7.7 (m, 8H, AreH), 9.2 (bs, 2H,
4.2.4. General procedure for synthesis of N-[2-(2-benzoyl-4-
methylphenoxy)-acetyl]-hydrazide methanone coumarins (5aej)
To a solution of o-hydroxy benzaldehyde (2 mmol) in alcohol
(20 ml), compounds 4aej (1.16 mmol) were added and the mixture
was refluxed for 4e5 h in the presence of catalytic amount of acetic
acid. The mixture was cooled and poured into ice-cold water, the
solid separated was filtered, dried and recrystallized from alcohol
to obtain compounds 5aej.
NH); 13C NMR (CDCl3):
d 13.66, 20.80, 39.35, 59.25, 78.3, 113.74,
123.35, 128.5, 129.75, 130.15, 131.85, 132.24, 133.95, 137.85, 160.65,
170.35, 171.1, 187.08. EI-MS: m/z 432.5 (Mþ, 48). Anal. Calcd. for
C
21H21ClN2O6 (432.5): C, 58.20; H, 4.85; N, 6.47. Found: C, 58.22; H,
4.87; N, 6.45%.
4.2.3.6. (N-{2-[2-(4-chloro-benzoyl)-4-methyl-phenoxy]-acetyl}
hydrazinocarbonyl)-ethyl acetate 4f. Yield 75%; M.p. 210e211 ꢂC; IR
(KBr): 1665 (C]O), 1655 (amide, C]O), 1745 (ester, C]O), 3230e
4.2.4.1. N-{2-[2-(4-methoxybenzoyl)-4-methylphenoxy]-acetyl}-hy-
drazide methanone coumarin 5a. Yield 69%; M.p. 200e202 ꢂC; IR
(KBr): 1640 (C]O), 1660 (amide, C]O), 1733 (ring C]O), 3250e
3320 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
1.35 (t, J ¼ 7 Hz, 3H, CH3 of
ester), 2.4 (s, 3H, CH3), 3.18 (s, 2H, CH2), 4.3 (q, J ¼ 6 Hz, 2H, CH2 of
ester), 4.6 (s, 2H, OCH2), 6.9e7.6 (m, 8H, AreH), 9.3 (bs, 2H, NH); 13
NMR (CDCl3): 13.66, 20.80, 39.35, 59.25, 78.3, 113.74, 123.35,
C
3340 cmꢃ1 (NHeNH); 1H NMR (CDCl3):
d
2.3 (s, 3H, CH3), 3.86 (s,
3H, OCH3), 4.7 (s, 2H, OCH2), 6.9e7.65 (m,11H, AreH), 8.72 (s,1H, ]
CH), 9.1 (bs, 2H, NH); 13C NMR (CDCl3):
20.9, 59.01, 78.02, 113.71,
113.82, 121.32, 123.31, 124.4, 125.2, 128.1, 129.71, 130.11, 131.1, 131.8,
d
128.5, 129.75, 130.15, 131.85, 132.24, 133.95, 137.85, 160.65, 170.35,
d
171.1, 187.08. EI-MS: m/z 432.5 (Mþ, 48). Anal. Calcd. for