RSC Advances
Paper
d ¼ 7.66–7.88 (d, 2H), 7.82–7.88 (m, 3H), 8.02–8.05 (m, 2H), (s, 1H, CH), 7.33–7.42 (m, 17H, ArH) ppm; 13C NMR (75 MHz,
8.35–8.38 (d, 2H) ppm; 13C NMR (75 MHz, CDCl3): d ¼ 123.4, DMSO-d6): d ¼ 12.2, 31.4, 106.0, 120.5, 123.7, 125.4, 125.5,
123.5, 128.3, 129.6, 131.9, 132.1, 135.2, 135.3, 135.4, 140.1, 126.1, 126.2, 127.4, 129.0, 129.1, 129.1, 131.2, 134.1, 137.0,
142.6, 145.1, 188.7 (CO), 189.6 (CO) ppm; elemental analysis: 137.7, 146.1, 158.8 ppm; elemental analysis: requires: C, 76.52;
require: C, 61.37; H, 2.90; O, 10.22% (C16H9O2Br) found: C, H, 5.39; O, 6.58% (C31H26N4O2) found: C, 76.55; H, 5.32; O,
61.41; H, 2.91; O, 10.19%.
6.60%.
2-(4-Cyanobenzylidene)-2H-indene-1, 3-dione (Table 2, entry
3r): yellow solid; mp 238–240 ꢀC; IR (KBr): nmax/cmꢁ1 ¼ 2227
Acknowledgements
1
(CN), 1727 and 1689 (CO), 1589, 989, 733 cmꢁ1; H NMR (300
MHz, CDCl3): d ¼ 7.80–7.92 (m, 5H), 8.05–8.08 (q, 2H), 8.51–8.54 We gratefully acknowledged the nancial support from the
(d, 2H) ppm; 13C NMR (75 MHz, CDCl3): d ¼ 115.5, 117.9, 123.6, Department of Science Technology and University Grants
123.7, 131.8, 132.2, 133.7, 135.6, 135.7, 136.6, 140.2, 142.6, Commission for FIST and SAP respectively. One of the authors
143.2, 188.2 (CO), 188.9 (CO) ppm; mass (EI): m/z ¼ 282; Madhuri Barge thanks the Department of Science Technology,
elemental analysis: requires: C, 78.76; H, 3.50; O, 12.34% New Delhi, India for the award of PURSE fellow.
(C17H9NO2) found: C, 78.80; H, 3.52; O, 12.32%.
4,40-(Phenylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-
References
ol) (Table 3, entry 6a): pale yellow solid; mp 170–172 ꢀC; IR
1
(KBr): nmax/cmꢁ1 ¼ 2620 (OH), 1615, 1489, 780 cmꢁ1; H NMR
(300 MHz, DMSO-d6): d ¼ 2.30 (s, 6H, CH3), 4.98 (s, 1H, CH),
7.12–7.16 (m, 1H, ArH), 7.21–7.25 (m, 6H, ArH), 7.38–7.42 (t, 4H,
ArH), 7.58–7.62 (d, 4H, ArH) ppm; 13C NMR (75 MHz, DMSO-d6):
d ¼ 12.0, 33.5, 121.3, 126.4, 126.5, 127.7, 128.7, 129.5, 137.4,
142.5, 146.8 ppm; elemental analysis requires: C, 74.29; H, 5.54;
O, 7.33% (C27H24 N4O2) found: C, 74.31; H, 5.50; O, 7.38%.
4,40-[(4-Chlorophenyl)methylene]bis(3-methyl-1-phenyl-1H-
pyrazol-5-ol) (Table 3, entry 6e): white solid; mp 215–217 ꢀC; IR
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1
(KBr): nmax/cmꢁ1 ¼ 2553 (OH), 1598 cmꢁ1; H NMR (300 MHz,
DMSO-d6): d ¼ 2.31 (s, 6H, CH3), 4.86 (s, 1H, CH), 7.18–7.21 (d,
6H, ArH), 7.34–7.39 (t, 4H, ArH), 7.69–7.02 (d, 4H, ArH), 13.69
(brs, 1H, OH) ppm; 13C NMR (75 MHz, CDCl3): d ¼ 11.8, 3 3.1,
120.9, 125.6, 128.2, 128.8, 129.1, 131.5, 137.6, 140.7, 145.9 ppm;
elemental analysis: requires: C, 68.86; H, 4.92; O, 6.79%
(C27H23N4O2Cl) found: C, 68.80; H, 4.94; O, 6.75%.
4,40-[(2-Thienyl)methylene]bis(3-methyl-1-phenyl-1H-pyr-
azol-5-ol) (Table 3, entry 6k): off white solid; mp 190–193 ꢀC; IR
(KBr): nmax/cmꢁ1 ¼ 2600, 1525 cmꢁ1; 1H NMR (300 MHz, DMSO-
d6): d ¼ 2.32 (s, 6H, CH3), 5.04 (s, 1H, CH), 6.74–6.75 (d, 4H,
ArH), 6.84 (s, 1H, ArH), 7.17–7.22 (t, 3H, ArH), 7.37–7.41 (t, 3H,
ArH), 13.88 (brs, 1H, OH) ppm; 13C NMR (75 MHz, CDCl3): d ¼
11.8, 30.7, 120.8, 124.0, 124.9, 125.7, 126.9, 128.9, 145.7, 147.6
ppm; elemental analysis: requires: C, 67.85; H, 5.01; O, 7.23%
(C25H22N4O2S) found: C, 67.80; H, 5.05; O, 7.27%.
´ ˆ
4,40-[(2-Formyl)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-
ꢀ
5-ol) (Table 3, entry 6l): white solid; mp 247–250 C; IR (KBr):
1
nmax/cmꢁ1¼ 2552 (OH), 1688 (CO), 1598, cmꢁ1; H NMR (300
MHz, DMSO-d6): d ¼ 2.34 (s, 6H, CH3), 4.96 (s, 1H, CH), 7.15–
7.20 (m, 2H, ArH), 7.34–7.47 (m, 4H, ArH), 7.57–7.59 (d, 2H,
ArH), 7.70–7.73 (m, 6H), 9.92 (s, 1H), 13.80 (brs, 1H, OH) ppm;
13C NMR (75 MHz, CDCl3): d ¼ 11.9, 33.5, 104.7, 120.9, 125.7,
127.8, 128.5, 128.9, 129.1, 133.8, 136.5, 137.6, 143.4, 146.1, 10 (a) R. Makkar and S. Cameotra, Appl. Microbiol. Biotechnol.,
157.6, 192.6 ppm; elemental analysis: requires: C, 72.40; H,
5.21; O, 10.33% (C28H24N4O3) found: C, 72.44; H, 5.18; O,
10.37%.
2002, 58, 428; (b) S. Itoh, Fat Sci. Technol., 1987, 89, 470; (c)
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11 V. Singh, P. Tripathi, J. R. Patel, M. L. Kori and V. K. Dixit, Int.
J. Pharm. Clin. Res., 2009, 1, 40.
4,40-[(1-Naphthyl)methylene]bis(3-methyl-1-phenyl-1H-pyr-
azol-5-ol) (Table 3, entry 6m): white solid; mp 208–210 ꢀC; IR 12 D. C. Jain, Phytochemistry, 1987, 26, 2223.
(KBr): nmax/cmꢁ1 ¼ 2585 (OH), 1608, 1544, 1497, 1402, 784 13 (a) A. Kumbhar, S. Kamble, M. Barge, G. Rashinkar and
1
cmꢁ1; H NMR (300 MHz, CDCl3): d ¼ 2.32 (s, 6H, CH3), 5.52
R. Salunkhe, Tetrahedron Lett., 2012, 53, 2756; (b)
31182 | RSC Adv., 2014, 4, 31177–31183
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