TABLE 2. IR and 1H NMR Spectra of Compounds 3-5
Com-
IR spectrum, ν, cm-1
1H NMR spectrum*, δ, ppm (J, Hz)
pound
3388 (NH),
3.11 (1H, dd, 2J = 17, 3J = 6, 3-H);
3a
2670-2520 (br, OH),
1614, 1582, 1532
3.60 (1H, dd, 2J = 17, 3J = 8, 3-H); 6.50-6.90 (3H, m,
2-H + 3-, 5-HHet); 7.50 (1H, dt, 4-HHet);
7.91 (1H, d, 3J = 10, NH); 8.05 (1H, dt, 6-HHet);
9.70 (1H, br. s, OH)
3315 (NH),
2480 (br, OH),
1597, 1537
3.20 (1H, dd, 2J = 17, 3J = 6, 3-H); 3.65 (1H, dd,
2J = 17, 3J = 8, 3-H); 6.45 (1H, ddd, 2-H);
3b
3c
3d
7.20 (2H, m, 4-, 5-HHet); 7.50 (1H, d, 3J = 10, NH);
7.95 (1H, t, 6-HHet); 8.15 (1H, m, 2-HHet); 9.70 (1H, br. s, OH)
3344 (NH),
3.13 (1H, dd, 2J = 17, 3J = 6, 3-H); 3.60 (1H, dd,
2J = 17, 3J = 8, 3-H); 6.45 (1H, ddd, 2-H);
2480 (br, OH),
1616, 1588, 1528
6.73 (2H, dd, 3-, 5-HHet); 7.90 (1H, d, 3J = 10, NH);
8.16 (2H, dd, 2-, 6-HHet); 9.50 (1H, br. s, OH)
3516 (NH), 3284 (NH),
3120-2750 (br, OH),
1590, 1558, 1516
3.13 (1H, dd, 2J = 17, 3J = 6, 3-H); 3.56 (1H, dd,
2J = 17, 3J = 8, 3-H); 6.45 (1H, m, 2-H); 7.70 (1H, br. s, NH);
8.15 (1H, s, 5-HHet); 9.60 (1H, br. s, OH);
13.00 (1H, br. s, NHHet
)
3412 (NH), 3264 (NH),
3076-2780 (br, OH),
1638, 1544
3.17 (1H, dd, 2J = 17, 3J = 6, 3-H); 3.67 (1H, dd,
2J = 17, 3J = 8, 3-H); 6.33 (1H, m, 2-H); 8.63 (1H, d,
3J = 10, NH); 9.80 (1H, br. s, OH); 15.40 (1H, br. s, NHHet
3e
3f
)
3332 (NH), 3260, 2976
3.24 (1H, dd, 2J = 17, 3J = 6, 3-H); 3.58 (1H, dd,
(br, OH), 1590, 1522
2J = 17, 3J = 8, 3-H); 6.78 (2H, m, 2-H + 5-HHet); 8.38 (2H, d,
4-, 6-HHet); 8.47 (1H, d, 3J = 10, NH); 9.70 (1H, br. s, OH)
3384, 3248 (NH), 2470
(br, OH), 1557, 1515
3.11 (1H, dd, 2J = 17, 3J=6, 3-H); 3.64 (1H, dd,
2J = 17, 3J = 8, 3-H); 6.45 (1H, ddd, 2-H);
3g
6.80 (1H, d, 3J = 4, 4-HHet); 7.11 (1H, d, 3J = 4, 5-HHet);
8.90 (1H, d, 3J = 10, NH); 9.80 (1H, br. s, OH)
3300 (NH), 3087-2967
(CH quinoline),
3.22 (1H, dd, 2J = 17, 3J = 6, 3-H); 3.71 (1H, dd,
2J = 17, 3J = 8, 3-H); 6.53 (1H, ddd, 2-H);
7.20-8.60 (6H, m, HHet); 7.69 (1H, d, 3J = 10, NH);
9.80 (1H, br. s, OH)
3h
2450 (br, OH),
1632,1588, 1554, 1502
3423 (NH),
3175 (br, OH),
1594, 1528
3.00 (2H, t, 3J = 6, CH2); 3.33 (2H, t, 3J = 6, CH2);
4a
4b
4c
6.53 (1H, t, 5-HHet); 7.20 (1H, br. t, NH);
8.24 (2H, d, 4-, 6-HHet
)
3240, 3140 (NH, OH),
3.04 (2H, t, 3J = 4, CH2); 3.29 (2H, t, 3J = 4, CH2);
6.60 (1H, d, 3J = 4, 4-HHet); 7.00 (1H, d, 3J = 4, 5-HHet);
7.80 (1H, br. t, NH); 9.90 (2H, br. s, OH)
1612, 1566, 1510
3383 (NH), 2960-2860
(CH quinoline),
2580 (br, OH),
1624, 1548
3235 (NH), 3140-2930,
1660 (C=O quinone),
1573 (C=C quinone),
1537
3.12 (2H, t, 3J = 4, CH2); 3.25 (2H, t, 3J = 4, CH2);
6.42 (1H, br. t, NH); 6.80-8.50 (6H, m, HHet);
9.50 (1H, br. s, OH); 9.70 (1H, br. s, OH)
3.06 (2H, t, 3J = 6, CH2); 3.63 (2H, t, 3J = 6, CH2);
5a
5b
5c
5.42 (1H, br. t, NH); 6.49 (1H, t, 5-HHet);
8.18 (2H, d, 4-, 6-HHet
)
3207 (NH), 3115, 3067,
3.50 (4H, two overlapping triplets, 3J = 6, 2CH2);
6.56 (1H, d, 3J = 4, 4-HHet); 6.87 (1H, d, 3J = 4, 5-HHet);
7.60 (1H, br. t, NH)
2947, 2916, 1682
and 1670 (C=O), 1596,
1572 (C=C quinone)
3275 (NH), 3100-3020,
3.17 (2H, t, 3J = 6, CH2); 4.20 (2H, t, 3J = 6, CH2);
1660 (C=O), 1620, 1560 7.50-9.00 (6H, HHet); 9.70 (1H, br. t, NH)
(C=C quinone)
_______
1
* H NMR spectrum of compound 5a was recorded in CDCl3 and the
remaining compounds in DMSO-d6.
1620