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ArH), 8.06 (s, 1H, N]CH), 8.42 (s, 1H, ArH), 8.95 (s, 1H, ArH), 108.80, 112.09, 117.39, 121.35, 122.06, 127.33, 127.93, 128.53,
8.97 (s, 1H, ArH), 12.96 (s, 1H, –OH), 13.10 (s, 1H, –NH); 13C 139.33, 146.04, 148.60, 149.51, 151.28, 160.97, 160.97, 175.74.
NMR (100 MHz, DMSO-d6): d ppm 111.02, 117.49, 117.82, MS: m/z ¼ 420 (M + 1). Anal. calcd. For C20H16F3N3O4; calcd: C,
120.45, 129.02, 129.14, 130.23, 131.15, 138.33, 139.54, 139.77, 57.28; H, 3.85; N, 10.02; found: C, 57.35; H, 3.85; N, 10.00%.
146.48, 156.00, 153.15, 160.78, 175.02; MS: m/z ¼ 536 (M + 1).
Anal. calcd. For C27H17ClF3N5O2; calcd: C, 60.51; H, 3.20; N, acid thiophen-2-ylmethylene-hydrazide (7c). IR (neat,
13.07; found: C, 60.58; H, 3.21; N, 13.05%.
nmax cmꢀ1): 3407 (O–H), 3061 (N–H), 2983, 2922 (C–H-str), 1649
4.5.4. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic (C]O), 1607 (C]N); 1H NMR (400 MHz, DMSO-d6): d ppm
4.5.8. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic
acid
[3-(4-nitro-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]- 7.15–7.18 (m, 1H, ArH), 7.47 (d, 1H, ArH, J ¼ 7.6 Hz), 7.69–7.70
hydrazide (6d). IR (neat, nmax cmꢀ1): 3464 (O–H), 3233 (N–H), (m, 1H, ArH), 7.83 (d, 1H, ArH, J ¼ 8.5 Hz), 8.15 (s, 1H, N]CH),
3073, 2923 (C–H-str), 1650 (C]O), 1596 (C]N), 1534 (N–O), 8.49 (d, 1H, ArH, J ¼ 8.4 Hz), 8.71 (s, 1H, ArH), 9.01 (s, 1H, ArH),
1495 (N–O); 1H NMR (400 MHz, DMSO-d6): d ppm 7.41–7.45 (m, 13.03 (s, 1H, –OH), 13.12 (s, 1H, –NH); 13C NMR (100 MHz,
1H, ArH), 7.56–7.60 (m, 2H, ArH), 7.83 (dd, 1H, ArH, J ¼ 8.76 Hz, DMSO-d6): d ppm 120.31, 122.54, 122.81, 123.10, 127.13, 127.74,
J ¼ 1.56 Hz), 8.04–8.07 (m, 2H, ArH), 8.14 (s, 1H, N]CH), 8.23– 146.29, 149.15, 151.06, 160.27, 161.92, 174.35; MS: m/z ¼ 366 (M
8.26 (m, 2H, ArH), 8.36–8.39 (m, 2H, ArH), 8.49 (d, 1H, ArH, J ¼ + 1). Anal. calcd. For C16H10F3N3O2S; calcd: C, 52.60; H, 2.76; N,
8.4 Hz), 8.56 (s, 1H, ArH), 9.0 (s, 2H, ArH), 13.03 (s, 1H, –OH), 11.50; found: C, 52.66; H, 2.72; N, 11.53%.
13.14 (s, 1H, –NH); 13C NMR (100 MHz, DMSO-d6): d ppm
4.5.9. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic
111.81, 117.72, 117.81, 120.63, 129.84, 129.97, 131.04, 131.26, acid (4-dimethyl amino-benzylidene)-hydrazide (7d). IR
138.59, 139.87, 139.94, 147.00, 156.12, 153.25, 161.02, 175.49; (neat, nmax cmꢀ1): 3417 (O–H), 3100 (N–H), 3075, 3010 (C–H-str),
MS: m/z ¼ 547 (M + 1). Anal. calcd. For C27H17F3N6O4; calcd: C, 1645 (C]O), 1602 (C]N); 1H NMR (400 MHz, DMSO-d6): d ppm
59.34; H, 3.14; N, 15.38; found: C, 59.38; H, 3.11; N, 15.40%.
2.97 (s, 6H, NCH3), 6.77 (d, 2H, ArH, J ¼ 8.9 Hz), 7.58 (d, 1H, ArH,
4.5.5. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic J ¼ 8.9 Hz), 7.76 (d, 1H, ArH, J ¼ 8.4 Hz), 8.12 (s, 1H, N]CH), 8.26
acid
(1-phenyl-3-p-tolyl-1H-pyrazol-4-ylmethylene)-hydrazide (s, 1H, ArH), 8.48 (d, 1H, ArH, J ¼ 8.4 Hz), 9.00 (s, 1H, ArH), 13.11
(6e). IR (neat, nmax cmꢀ1): 3385 (O–H), 3130 (N–H), 3014, 2919 (s, 1H, –OH), 13.14 (s, 1H, –NH); 13C NMR (100 MHz, DMSO-d6): d
(C–H-str), 1663 (C]O), 1605 (C]N); 1H NMR (400 MHz, DMSO- ppm 47.05, 53.04, 111.73, 112.04, 117.72, 121.36, 122.38, 127.02,
d6): d ppm 2.41(s, 3H, CH3), 7.36–7.40 (m, 3H, ArH), 7.55 (t, 2H, 129.09, 138.96, 145.97, 148.92, 151.27, 160.14, 175.51. MS: m/z ¼
ArH, J ¼ 8.0 Hz), 7.70 (d, 2H, ArH, J ¼ 7.8 Hz), 7.83 (d, 1H, ArH, J 403 (M + 1). Anal. calcd. For C20H17F3N4O2; calcd: C, 59.70; H,
¼ 8.7 Hz), 8.01 (d, 2H, ArH, J ¼ 8.0 Hz), 8.13 (s, 1H, N]CH), 8.46 4.26; N, 13.92; found: C, 59.68; H, 4.25; N, 13.82%.
(s, 1H, ArH), 8.47 (d, 1H, ArH, J ¼ 8.7 Hz), 8.98 (s, 1H, ArH), 9.02
4.5.10. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic
(s, 1H, ArH), 12.96 (s, 1H, –OH), 13.13 (s, 1H, –NH); 13C NMR acid (3-ethoxy-2-hydroxy-benzylidene)-hydrazide (7e). IR (neat,
(100 MHz, DMSO-d6): d ppm 21.18, 111.68, 117.25, 117.42, nmax cmꢀ1): 3400 (O–H), 3222 (O–H), 3189 (N–H), 3049, 2985 (C–
1
121.32, 127.88, 128.83, 129.80, 130.06, 138.51, 139.12, 139.38, H-str), 1660 (C]O), 1615 (C]N), 1206 (O–CH3); H NMR (400
139.56, 141.27, 146.11, 152.07, 160.96, 175.49. MS: m/z ¼ 516 (M MHz, DMSO-d6): d ppm 1.37 (t, 3H, CH3, J ¼ 6.8 Hz), 4.07 (q, 2H,
+ 1). Anal. calcd. For C27H17F3N6O4; calcd: C, 65.24; H, 3.91; N, OCH2, J ¼ 4.4 Hz), 6.87 (t, 1H, ArH, J ¼ 8.4 Hz), 7.03 (d, 1H, ArH, J
13.59; found: C, 65.30; H, 3.89; N, 13.55%.
¼ 7.7 Hz), 7.12 (d, 1H, ArH, J ¼ 7.0 Hz), 7.84 (d, 1H, ArH, J ¼ 7.1
4.5.6. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic Hz), 8.15 (s, 1H, N]CH), 8.50 (d, 1H, ArH, J ¼ 7.0 Hz), 8.69 (s, 1H,
acid (4-methoxy-benzylidene)-hydrazide (7a). IR (neat, ArH), 9.04 (s, 1H, ArH), 11.14 (s, 1H, –OH), 13.13 (s, 1H, –OH),
nmax cmꢀ1): 3407 (O–H), 3163 (N–H), 3063, 2978 (C–H-str), 1647 13.18 (s, 1H, –NH); 13C NMR (100 MHz, DMSO-d6): d ppm 21.40,
(C]O), 1605 (C]N), 1165 (O–CH3); 1H NMR (400 MHz, CDCl3): 64.52, 111.84, 117.13, 121.98, 122.45, 123.08, 126.33, 127.81,
d ppm 2.95 (s, 3H, OCH3), 6.17 (d, 2H, ArH, J ¼ 8.2 Hz), 6.86 (d, 128.05, 140.00, 145.99, 150.21, 159.27, 160.87, 160.97, 176.02; MS:
2H, ArH, J ¼ 8.2 Hz), 6.96 (d, 2H, ArH, J ¼ 8.0 Hz), 7.28 (s, 1H, m/z ¼ 420 (M + 1). Anal. calcd. For C20H16F3N3O4; calcd: C, 57.28;
N]CH), 7.53 (s, 1H, ArH), 7.63 (d, 1H, ArH, J ¼ 8.0 Hz), 8.15 (s, H, 3.85; N, 10.02; found: C, 57.30; H, 3.86; N, 10.00%.
1H, ArH); 13C NMR (100 MHz, CDCl3): d ppm 55.13, 108.83,
4.5.11. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic
112.10, 117.32, 121.34, 122.01, 127.33, 127.85, 128.61, 139.41, acid (4-diethylamino-2-hydroxy-benzylidene)-hydrazide (7f). IR
146.05, 148.55, 149.52, 151.38, 160.98, 160.99, 175.87; MS: m/z ¼ (neat, nmax cmꢀ1): 3466 (O–H), 3237 (O–H), 3110 (N–H), 2975,
1
390 (M + 1). Anal. calcd. For C19H14F3N3O3; calcd: C, 58.61; H, 2927 (C–H-str), 1621 (C]O), 1586 (C]N); H NMR (400 MHz,
3.62; N, 10.79; found: C, 58.72; H, 3.62; N, 10.78%.
DMSO-d6): d ppm 1.12 (t, 6H, CH3, J ¼ 6.9 Hz), 3.37 (q, 4H,
4.5.7. 4-Hydroxy-7-triuoromethyl-quinoline-3-carboxylic NCH2, J ¼ 7.0 Hz), 6.13 (s, 1H, ArH), 6.29 (dd, 1H, ArH, J ¼ 8.8
acid (3,4-dimethoxy-benzylidene)-hydrazide (7b). IR (neat, Hz, J ¼ 2.4 Hz), 7.22 (d, 1H, ArH, J ¼ 8.8 Hz), 7 0.83 (dd, 1H, ArH,
nmax cmꢀ1): 3410 (O–H), 3170 (N–H), 3015, 2969 (C–H-str), 1661 J ¼ 8.6 Hz, J ¼ 1.4 Hz), 8.14 (s, 1H, N]CH), 8.46 (s, 1H, ArH),
(C]O), 1582 (C]N), 1173 (O–CH3), 1156 (O–CH3); 1H NMR (400 8.49 (d, 1H, ArH, J ¼ 8.4 Hz), 9.00 (s, 1H, ArH), 11.37 (s, 1H,
MHz, DMSO-d6): d ppm 3.82 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), –OH), 12.91 (s, 1H, –OH), 13.10 (s, 1H, –NH); 13C NMR (100
7.06 (d, 1H, ArH, J ¼ 4.4 Hz), 7.28 (dd, 1H, ArH, J ¼ 8.3 Hz, J ¼ MHz, DMSO-d6): d ppm 17.54, 54.01, 111.66, 117.62, 121.87,
1.8 Hz), 7.39 (d, 1H, ArH, J ¼ 1.8 Hz), 7.82 (dd, 1H, ArH, J ¼ 8.6 122.50, 123.16, 126.28, 127.15, 128.10, 145.83, 150.12, 159.30,
Hz, J ¼ 1.3 Hz), 8.15 (s, 1H, N]CH), 8.38 (s, 1H, ArH), 8.50 (d, 160.88, 161.00, 175.95; MS: m/z ¼ 447 (M + 1). Anal. calcd. For
1H, ArH, J ¼ 8.4 Hz), 9.02 (s, 1H, ArH), 13.02 (s, 1H, –OH), 13.11
C22H21F3N4O3; calcd: C, 59.19; H, 4.74; N, 12.55; found: C, 59.20;
(s, 1H, –NH); 13C NMR (100 MHz, DMSO-d6): d ppm 55.97, H, 4.72; N, 12.15%.
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RSC Adv., 2014, 4, 30864–30875 | 30871