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K. Nepali et al. / Bioorg. Med. Chem. 19 (2011) 1950–1958
J = 8.7 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 7.91 (d, J = 7.8 Hz, 2H), 7.54–
7.70 (m, 4H), 7.36–7.48 (m, 3H), 6.13 (dd, J = 5.1 and 12 Hz, 1H),
4.27 (dd, J = 12 and 18 Hz, 1H), 3.36 (dd, J = 5.1 Hz and 18 Hz,
1H), 2.57 (s, 3H); 13C (75 MHz, CDCl3, TMS = 0) d = 168.90,
154.94, 147.17, 137.04, 134.34, 134.11, 131.53, 130.47, 128.90,
128.60, 128.47, 127.81, 127.31, 126.51, 126.41, 126.38, 125.47,
124.78, 55.90, 45.11, 22.05. Anal. Calcd for C21H17N3O3: C, 70.18;
H, 4.77; N, 11.69. Found: C, 70.23; H, 5.08; N, 11.69.
5.2.25. 1-(4,5-Dihydro-5-(4-hydroxy-3-methoxyphenyl)-3-
(naphth-1-yl)-1H-pyrazol-1-yl)ethanone (36)
White solid; yield 83%; mp: 182–184 °C; IR (KBr): 3443 (O–H),
1662 (C@O), 1578 (C@N) cmÀ1; 1H NMR (300 MHz, CDCl3, TMS = 0)
d = 9.26 (d, J = 8.7 Hz, 1H), 7.92 (d, J = 8.1 Hz, 2H), 7.56–7.71 (m, 3H),
7.49 (t, J = 8.1 Hz, 1H), 6.83 (m, 3H), 5.49 (dd, J = 4.2 Hz and 11.7 Hz,
1H), 3.94 (dd, J = 11.7 Hz and 17.4 Hz, 1H), 3.90 (s, 3H). 3.34 (dd,
J = 4.2 Hz and 17.4 Hz, 1H), 2.49 (s, 3H). Anal. Calcd for C22H20N2O3:
C, 73.32; H, 5.59; N, 7.77. Found: C, 73.61; H, 5.25; N, 7.69.
5.2.21. 1-(4,5-Dihydro-5-(2,5-dimethoxyphenyl)-3-(naphth-1-
yl)-1H-pyrazol-1-yl)ethanone (32)
5.2.26. 1-(5-(2,3-Dichlorophenyl)-4,5-dihydro-3-(naphth-1-yl)-
1H-pyrazol-1-yl)ethanone (37)
White solid; yield 78%; mp: 163–165 °C; IR (KBr): 1664 (C@O),
1585 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 9.25 (d,
;
White solid; yield 89%; mp: 115–117 °C; IR (KBr): 1666 (C@O),
1585 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 9.25 (d,
;
J = 8.4 Hz, 1H), 7.86 (d, J = 7.5 Hz, 2H), 7.64 (t, J = 7.2 Hz, 1H), 7.54
(m, 2H) ,7.41 (t, J = 7.8 Hz, 1H), 6.69–6.82 (m, 3H), 5.79 (dd,
J = 4.2 Hz and 11.7 Hz, 1H), 3.91(dd, J = 11.7 Hz and 17.4 Hz, 1H),
3.79 (s, 3H), 3.70 (s, 3H), 3.20 (dd, J = 4.2 Hz and 17.4 Hz, 1H),
2.55 (s, 3H). 13C (75 MHz, CDCl3, TMS = 0) d = 168.73, 155.15,
153.60, 150.27, 133.99, 130.92, 130.47, 130.36, 128.66, 128.11,
127.93, 127.51, 126.60, 126.20, 124.67, 112.63, 112.13, 111.83,
55.93, 55.54, 54.55, 44.01, 22.14. Anal. Calcd for C23H22N2O3: C,
73.78; H, 5.92; N, 7.48. Found: C, 73.44; H, 6.19; N, 7.69.
J = 8.44 Hz, 1H), 7.89 (d, J = 7.20 Hz, 2H), 7.52–7.66 (m, 3H), 7.24–
7.46 (m, 2H), 7.04–7.16 (m, 2H), 5.90 (d, J = 7.8 Hz, 1H), 4.05 (d,
J = 12.9 and 16.8 Hz, 1H) 3.23 (d, J = 16.8 Hz, 1H), 2.58 (s, 3H). 13C
(75 MHz, CDCl3, TMS = 0) d = 168.91, 154.73, 140.78, 134.08,
133.76, 131.42, 130.46, 130.10, 129.52, 128.85, 128.46, 127.77,
127.73, 127.36, 126.49, 126.39, 124.74, 124.02, 57.08, 43.84,
22.10. Anal. Calcd for C21H16Cl2N2O: C, 65.81; H, 4.21; N, 7.31.
Found: C, 65.79; H, 4.54; N, 7.70.
5.2.27. 1-(5-(Benzo[d][1,3]dioxol-5-yl)-4,5-dihydro-3-(naphth-
1-yl)-1H-pyrazol-1-yl)ethanone (38)
5.2.22. 1-(4,5-Dihydro-5-(3,4-dimethoxyphenyl)-3-(naphth-1-
yl)-1H-pyrazol-1-yl)ethanone (33)
White solid; yield 77%; mp: 126–128 °C; IR (KBr): 1666 (C@O),
White solid; yield 77%; mp: 118–120 °C; IR (KBr): 1663 (C@O),
1578 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d =9.27(d,
;
1591 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 9.26 (d,
;
J = 8.4 Hz, 1H), 7.88 (d, J = 8.1 Hz, 2H), 7.54(m, 5H), 6.76 (m, 2H),
5.87 (s, 2H) , 5.47 (dd, J = 3.9 and 11.7 Hz, 1H), 3.87 (dd, J = 17.4
and 11.7 Hz, 1H), 3.28 (dd, J = 3.9 and 17.4 Hz, 1H) , 2.50 (s, 3H).
13C (75 MHz, CDCl3, TMS = 0) d = 168.83, 154.36, 147.99, 146.93,
135.78, 134.00, 131.16, 130.41, 128.72, 128.25, 127.65, 127.57,
126.52, 126.28, 124.67, 119.01, 108.41, 105.95, 100.99, 58.49,
44.84, 22.13. Anal. Calcd for C22H18N2O3: C, 73.73; H, 5.06; N,
7.82. Found: C, 73.92; H, 5.28; N, 7.69.
J = 8.4 Hz, 1H), 7.86 (d, J = 7.8 Hz, 2H), 7.66 (t, J = 7.2 Hz, 1H),
7.50–7.56 (m, 2H), 7.42 (t, J = 7.8 Hz, 1H), 6.75–6.83 (m, 3H), 5.49
(dd, J = 4.2 Hz and 11.7 Hz, 1H), 3.89 (dd, J = 11.7 Hz and 17.4 Hz,
1H), 3.82 (s, 3H) , 3.78 (s, 3H), 3.31(dd, J = 4.2 Hz and 17.4 Hz,
1H), 2.51 (s, 3H); 13C (75 MHz, CDCl3, TMS = 0) d = 168.53,
154.21, 149, 148.25, 134.32, 133.84, 130.91, 130.27, 128.58,
128.06, 127.52, 127.44, 126.32, 126.11, 124.56, 117.40, 111.30,
108.95, 58.33, 55.62, 44.62, 22.00. Anal. Calcd for C23H22N2O3: C,
73.78; H, 5.92; N, 7.48. Found: C, 74.04; H, 5.79; N, 7.52.
5.2.28. 1-(4,5-Dihydro-5-(naphth-2-yl)-3-(naphth-1-yl)-1H-
pyrazol-1-yl)ethanone (39)
5.2.23. 1-(4,5-Dihydro-5-(3,4,5-trimethoxyphenyl)-3-(naphth-1-
yl)-1H-pyrazol-1-yl)ethanone (34)
White solid; yield 75%; mp: 142–144 °C; IR (KBr): 1664 (C@O),
1587 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS=0) d = 9.32(d,
;
White solid; yield 76%; mp: 135–137 °C; IR (KBr): 1653 (C@O),
J = 8.4 Hz, 1H), 7.89 (d, J = 8.1 Hz, 2H),7.74–7.81(m, 4H), 7.64–
7.70 (m, 1H)7.52–7.59 (m, 2H), 7.35–7.45(m, 4H), 5.71 (dd,
J = 4.5 Hz and 11 Hz, 1H), 3.96 (dd, J = 11.7 and 17.4 Hz, 1H), 3.39
(dd, J = 4.5 Hz and 17.4 Hz, 1H), 2.54 (s, 3H); 13C (75 MHz, CDCl3,
TMS = 0) d = 168.89, 154.38, 139.04, 134.07, 133.29, 132.85,
131.21, 130.51, 129.03, 128.80, 128.34, 127.92, 127.72, 127.65,
127.58, 126.62, 126.35, 126.22, 125.89, 124.75, 124.58, 123.39,
58.92, 44.86, 22.22. Anal. Calcd for C25H20N2O: C, 82.39; H, 5.53;
N, 7.69. Found: C, 82.68; H, 5.37; N, 7.72.
1592 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 9.23(d,
;
J = 8.7 Hz, 1H), 7.90 (d, J = 8.1 Hz, 2H), 7.55–7.68 (m, 3H), 7.46 (t,
J = 7.5 Hz, 1H), 6.50 (s, 2H) , 5.51 (dd, J = 4.2 and 11.7 Hz, 1H),
3.93 (dd, J = 11.7 Hz and 17.4 Hz, 1H), 3.81 (s, 9H), 3.35 (dd,
J = 4.2 Hz and 17.4 Hz, 1H), 2.54 (s, 3H); 13C (75 MHz, CDCl3,
TMS = 0) d = 168.89, 154.53, 153.57, 137.56, 137.35, 134.04,
131.16, 130.45, 128.77, 128.21, 127.62, 126.33, 126.30, 124.73,
102.37, 60.62, 58.99, 56.00, 45.04, 22.12. Anal. Calcd for
C24H24N2O4: C, 71.27; H, 5.98; N, 6.93. Found: C, 71.55; H, 6.58;
N, 6.98.
5.2.29. 1-(3-(Furan-2-yl)-4,5-dihydro-5-(2-nitrophenyl)pyrazol-
1-yl)ethanone (41)
5.2.24. 1-(4,5-Dihydro-5-(2,3,4-trimethoxyphenyl)-3-(naphth-1-
yl)-1H-pyrazol-1-yl)ethanone (35)
White solid; yield 78%; mp: 144–146 °C; IR (KBr): 1667 (C@O),
1590 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 8.12 (d,
;
White solid; yield 82%; mp: 120–122 °C; IR (KBr): 1661 (C@O),
J = 8.0 Hz, 1H), 7.26–7.60 (m, 4H), 6.75 (d, J = 3.4 Hz, 1H), 6.51 (dd,
J = 1.75 and 3.39 Hz, 1H), 6.12 (dd, J = 5.1 and 11.9 Hz, 1H), 3.99
(dd, J = 11.9 and 18.2 Hz, 1H), 3.08 (dd, J = 5.1 and 18.2 Hz, 1H),
2.45 (s, 3H); 13C (75 MHz, CDCl3, TMS = 0) d = 168.88, 147.04,
146.52, 146.09, 144.97, 136.72, 134.38, 128.56, 126.43, 125.50,
113.12, 112.03, 56.68, 42.28, 21.83. Anal. Calcd for C15H13N3O4: C,
60.20; H, 4.38; N, 14.04. Found: C, 60.18; H, 4.24; N, 14.32.
1587 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 9.29 (d,
;
J = 8.7 Hz, 1H), 7.89 (d, J = 8.1 Hz, 2H), 7.65 (t, J = 7.8 Hz, 1H),
7.54–7.58 (m, 2H), 7.45 (t, J = 7.8 Hz, 1H), 6.87 (d, J = 8.7 Hz, 1H),
6.60 (d, J = 8.7 Hz, 1H), 5.54 (dd, J = 4.8 Hz and 12.00 Hz, 1H),
3.90 (dd, J = 12.00 and 17.4 Hz, 1H), 3.94 (s, 3H), 3.86 (s, 3H),
3.81 (s, 3H), 3.30 (dd, J = 4.81 Hz and 17.4 Hz, 1H), 2.51 (s, 3H);
13C (75 MHz, CDCl3, TMS = 0) d = 168.74, 155.02, 153.25, 150.79,
142.27, 134.05, 130.97, 130.54, 128.73, 128.22, 127.96, 127.55,
126.61, 126.23, 124.77, 121.17, 107.23, 60.73, 60.67, 55.90, 54.92,
44.42, 22.26. Anal. Calcd for C24H24N2O4: C, 71.27; H, 5.98; N,
6.93. Found: C, 71.33; H, 5.82; N, 7.21.
5.2.30. 1-(3-(Furan-2-yl)-4,5-dihydro-5-(2,5-dimethoxyphenyl)-
(pyrazol-1-yl)ethanone (50)
Yellow solid; yield 80%; mp: 101–106 °C; IR (KBr): 1658 (C@O),
1586 (C@N) cmÀ1 1H NMR (300 MHz, CDCl3, TMS = 0) d = 7.53 (d,
;