TABLE 3. 1H NMR Spectra of Compounds 2–13, 14a–d, and 15a–c
Com-
δ, ppm (J, Hz)
pound
1
2
2
2.70 (3H, s, CH3); 2.79 (3H, s, CH3); 6.57 (1H, s, H-5); 6.77 (1H, dd, J = 3.5, J = 1.5,
H furan); 7.20 (1H, d, J = 3.5, H furan); 8.04 (1H, d, J = 1.5, H furan); 8.93 (1H, s,
N=CH); 12.13 (1H, br. s, NH)
3
1.25 (3H, t, J = 7.0, CH3CH2); 2.55 (3H, s, CH3); 2.65 (3H, s, CH3); 4.41 (2H, q,
J = 7.0, CH3CH2); 4.95 (2H, s, NCH2); 6.60 (1H, s, H-5); 6.79 (1H, dd, J = 3.5, J = 1.5,
H furan); 7.33 (1H, d, J = 3.5, H furan); 8.22 (1H, d, J = 1.5, H furan); 8.77 (1H, s,
N=CH)
4
5
2.66 (3H, s, CH3); 2.69 (3H, s, CH3); 4.65 (2H, s, NCH2); 6.33 (1H, s, H-5); 6.71 (1H,
dd, J = 3.5, J = 1.5, H furan); 7.53 (1H, d, J = 3.5, H furan); 7.77 (1H, d, J = 1.5, H furan);
8.81 (1H, s, N=CH)
2.61 (3H, s, CH3); 2.64 (3H, s, CH3); 2.91 (3H, s, OCOCH3); 3.65 (2H, t, J = 7.5,
OCH2CH2); 4.33 (2H, t, J = 7.5, OCH2CH2); 6.41 (1H, s, H-5); 6.77 (1H, dd, J = 3.5,
J = 1.5, H furan); 7.23 (1H, d, J = 3.5, H furan); 7.33 (1H, d, J = 1.5, H furan); 8.75 (1H,
s, N=CH)
6*
7
2.43 (3H, s, CH3); 2.44 (3H, s, CH3); 3.33 (2H, t, J = 7.5, NCH2); 4.21 (2H, t, J = 7.5,
OCH2); 4.65 (1H, br. s, OH); 6.32 (1H, s, H-5); 6.67 (1H, dd, J = 3.5, J = 1.5, H furan);
6.91 (1H, d, J = 3.5, H furan); 7.18 (1H, d, J = 1.5, H furan); 8.44 (1H, s, N=CH)
2.45 (3H, s, CH3); 2.51 (3H, s, CH3); 3.21 (2H, t, J = 7.5, NHCH2CH2); 3.86 (2H, m,
NHCH2CH2); 4.87 (2H, br. s, NH2); 6.19 (1H, s, H-5); 6.57 (1H, dd, J = 3.5, J = 1.5,
H furan); 7.08 (1H, d, J = 3.5, H furan); 7.32 (1H, d, J = 1.5, H furan); 8.51 (1H, s,
N=CH); 9.16 (1H, br.s, NH)
8*
2.62 (3H, s, CH3); 2.68 (3H, s, CH3); 3.91 (2H, t, J = 7.5, NHCH2CH2); 4.48 (2H, m,
NHCH2CH2); 6.98 (1H, s, H-5); 7.23 (1H, dd, J = 3.5, J = 1.5, H furan); 7.45 (1H, d,
J = 3.5, H furan); 7.88–8.32 (7H, m, H furan, NH, Ph); 8.61 (1H, s, N=CH); 9.16 (1H,
br. s, NH); 10.11 (1H, br. s, CSNH)
9
10
11
12
13
14a
2.43 (3H, s, CH3); 2.49 (3H, s, CH3); 4.88 (2H, s, CH2); 5.14 (2H, br. s, NHNH2); 6.71
(1H, s, H-5); 7.33 (1H, dd, J = 3.5, J = 1.5, H furan); 7.55 (1H, d, J = 3.5, H furan); 7.98 (1H,
d, J = 1.5, H furan); 8.41 (1H, s, N=CH); 10.14 (1H, br. s, CONH)
2.55 (3H, s, CH3); 2.68 (3H, s, CH3); 4.95 (2H, s, CH2); 6.98 (1H, s, H-5); 7.34 (1H, dd,
J = 3.5, J = 1.5, H furan); 7.77 (1H, d, J = 3.5, H furan); 7.93–8.54 (7H, m, H furan,
NH, Ph); 8.77 (1H, s, N=CH); 9.07 (1H, br. s, CSNH); 10.43 (1H, br. s, CONH)
2.51 (3H, s, CH3); 2.64 (3H, s, CH3); 5.33 (2H, s, NCH2); 6.33 (1H, s, H-5); 6.68 (1H,
dd, J = 3.5, J = 1.5, H furan); 7.13 (1H, d, J = 3.5, H furan); 7.55–7.76 (6H, m, H furan,
Ph); 8.19 (1H, s, N=CH); 11.55 (1H, br. s, NHPh)
2.50 (3H, s, CH3); 2.61 (3H, s, CH3); 5.39 (2H, s, NCH2); 6.23 (1H, s, H-5); 6.94 (1H,
dd, J = 3.5, J = 1.5, H furan); 7.09 (1H, d, J = 3.5, H furan); 7.22–7.75 (6H, m, H furan,
Ph); 8.22 (1H, s, N=CH); 12.05 (1H, br. s, SH)
2.54 (3H, s, CH3); 2.59 (3H, s, CH3); 5.71 (2H, s, NCH2); 6.13 (1H, s, H-5); 6.88 (1H,
dd, J = 3.5, J = 1.5, H furan); 7.06 (1H, d, J = 3.5, H furan); 7.45–7.86 (6H, m, H furan,
Ph); 8.33 (1H, s, N=CH); 11.12 (1H, br. s, NHPh)
2.63 (3H, s, CH3); 2.65 (3H, s, CH3); 3.41–4.21 (4H, m, 4 CHOH); 3.99–4.11 (5H, br. s,
5OH); 5.06 (2H, s, NCH2); 5.21 (2H, br. s, CH2OH); 6.74 (1H, s, H-5); 7.87 (1H, dd,
J = 3.5, 1.5, H furan); 7.90 (1H, d, J = 3.5, H furan ); 8.12 (1H, d, J = 1.5, H furan); 8.45
(1H, s, HNN=CH); 8.72 (1H, s, N=CH); 8.93 (1H, br. s, NH)
14b
14c
14d
2.53 (3H, s, CH3); 2.09 (3H, s, CH3); 3.20–4.40 (4H, m, 4 CHOH); 4.39–4.65 (5H, br. s,
5 OH); 4.71 (2H, s, NCH2); 5.51 (2H, br. s, CH2OH); 6.33 (1H, s, H-5); 6.63 (1H, dd,
J = 3.5, J = 1.5, H furan); 7.50 (1H, d, J = 3.5, H furan); 7.44 (1H, d, J = 1.5, H furan); 7.76
(1H, s, HNN=CH); 8.09 (1H, s, N=CH); 8.61 (1H, br. s, NH)
2.59 (3H, s, CH3); 2.66 (3H, s, CH3); 3.54–4.32 (3H, m, 3 CHOH); 4.43–4.56 (4H, br. s,
4 OH); 4.86 (2H, s, NCH2); 5.42 (2H, br. s, CH2OH); 6.55 (1H, s, H-5); 6.72 (1H, dd,
J = 3.5, J = 1.5, H furan); 7.55 (1H, d, J = 3.5, H furan); 7.66 (1H, d, J = 1.5, H furan); 7.81
(1H, s, HNN=CH); 8.16 (1H, s, N=CH); 8.75 (1H, br. s, NH)
2.55 (3H, s, CH3); 2.61 (3H, s, CH3); 3.61–4.22 (3H, m, 3 CHOH); 4.42–4.57 (4H, br. s,
4 OH); 4.84 (2H, s, NCH2); 5.39 (2H, br. s, CH2OH); 6.56 (1H, s, H-5); 6.77 (1H, dd,
J = 3.5, J = 1.5 H furan); 6.94 (1H, d, J = 3.5, H furan); 7.59 (1H, d, J = 1.5, H furan);
7.88 (1H, s, HNN=CH); 8.20 (1H, s, N=CH); 8.77 (1H, br. s, NH)
503