H. Nmrt, 1. , J. =. 1h, 1. , 1. et al., From 14a 32 Yield 80%70 (s, 1H), 13.20 (m, 1H); 13 C NMR (DMSOd 6 , 100 MHz) d 52.1, 101(4 0 -Iodo-2 0 -methoxycarbonylphenylamino)benzoic acid (17b) From 14b. 31 Yield 59%; mp 230?232 °C; IR (KBr) 3200 1209 cm À1 -methoxycarbonylphenylamino)benzoic acid (17c). From 14c. 33 Yield 67%; mp 191?193 °C, 9 Hz), 7.46 (m, 2H), 7.74 (d, 1H, J = 9 Hz), 7.93 (d, 1H, J = 8 Hz), 8.14 (s, 1H), 10.78 (s, 1H), 13.21 (m, 1H), pp.206-208, 1254.

1. , J. =. 1h, and N. , From 17a. Yield 85%; R f = 0 1273 cm À1, MS m/z 379 (M + , 71) H NMR (CDCl 3 , 400 MHz) d 4.01 (s, 3 H), 7.29 (m, 2H), pp.189-191, 1508.

H. Nmrt, 1. , 1. , 1. , 6. et al., From 17c56 (br s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 53-Diethylaminoethyl)-9,10-dihydro-1-iodo-9-oxoac- ridine-4-carboxamide hydrochloride salt (8a) From 24a. Yield 81%; mp 269?271 °C; IR (KBr) 3500?3100, 3057, 1613, 1577, 1513 cm À149 (br s, 1H), 10.39 (br s, 1H), 12.70 (br s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 82, 175.2. Anal. Calcd for C 20 H 22 IN 3 O 2 , HCl, 3H 2 O: C, 43.38; H, 5.28; N, 7.59. Found: C, 43.74; H, 4.99; N, 7.68. 4.1.10.2. N-(2-Diethylaminoethyl)-9,10-dihydro-2-iodo-9-oxoac- ridine-4-carboxamide hydrochloride salt (8b) From 24b. Yield 71%; mp 298?300 °C; IR (KBr) 3400?320060 (s, 1H), 8.68 (s, 1H), 9.42 (br s, 1H), 10.27 (br s, 1H), 12.19 (br s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.3 (2C), 34.2, 46Diethylaminoethyl)-9,10-dihydro-5-iodo-9-oxoac- ridine-4-carboxamide hydrochloride salt (8d) from 24d. From 24d. Yield 82%; mp 251?253 °C; IR (KBr), MHz) d 4.07 H NMR (DMSO-d 6 , 400 MHz) d 1.27 (t, 6H, J 8 7 Hz), 3.23 (m, 4H), 3.32 (m, 2H), 3.76 (m, 2H), 7.32 (t, 1H, J 8 8 Hz), 7.75 (m, 2H), 7.95 (d, 1H, J 8 8.5 Hz), 7.99 (d, 1H, J = 8.5 Hz), 8.21 (d, 1H, J = 8 Hz), 9.05 (m, 1H), 10.17 (br s, 1H), 10.79 (br s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.4 (2C), 34.5, 46.6 (2C) H NMR (DMSO-d 6 , 400 MHz) d 1.27 (t, 6H, J = 7 Hz), 3.24 (m, 4H), 3.36 (m, 2H), 3.79 (m, 2H), 7.12 (t, 1H, J = 8 Hz), 7.43 (t, 1H, J = 7.5 Hz), 8.26 (d, 1H, J = 8 Hz), 8.32 (d, 1H, J = 7 Hz), 8.46 (d, 1H, J = 8 Hz), 8.55 (d, 1H, J = 7 Hz), 9.55 (br s, 1H), 10.34 (br s, 1H) 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.3 (2C), pp.41-202, 1300.

H. Nmrt, 6. , 4. , 2. , 1. et al., (br s, 1 H); 13 C NMR (CDCl 3 , 100 MHz) d 11, pp.400-401

H. Nmrt, 6. , 4. , 1. , 1. et al., 60 (s, 1H)76 (s, 1H); 13 C NMR (CDCl 3 , 100 MHz) d 11 N-(2-Diethylaminoethyl)-6-iodoacridine-4-carboxamide (30e) From 29e. The mixture was refluxed in dry dichloromethane for 4 h. Yield 52%; R f = 0, MHz) d 12C), 38.4, 47.5 (2C) 1 H NMR (CDCl 3 MHz) d 1.16 (t, 6H, J = 7 Hz), 2.79 (m, 6H), 3.77 Hz), 8.78 (s, 1H), 8.81 (s, 1 H), 8.97 (d, 1H, J = 7 Hz), 11.90 (br s, 1H); 13 C NMR (CDCl 3 , 50 MHz) d 12.0 (2C), pp.3500-3300, 0200.

H. Nmrt, 6. , 1. , and J. =. , 01 (br s, 1H); 13 C NMR (CDCl 3 , 100 MHz) d 10, MHz) d 1.26 8.5, 7 Hz), 8.06 (d, 1H, J = 9 Hz) 1H), 8.98 (d, 1H, J = 7 Hz), p.984778, 1998.

H. Nmr, Compound 33 was prepared from compound 24c as described for the synthesis of methyl iodoacridan-4-carboxylates 28. The product was chromatographed (Al 2 O 3 Yield 60%; R f = 0Al 2 O 3 , CH 2 Cl 2 /EtOH, 99.5:0.5, v/v); mp 106?108 °C; IR (KBr) 3268, 2346, 1636, 1449, 1164 cm À1, 6H), 3.91 (q, 2 H, J = 6.5 Hz), 3.98 (s, 2H), pp.31-32

H. Nmrq, 4. , 2. , 2. , J. =. 1h et al., From 30c40 (s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8 N-(2-Diethylaminoethyl)-5-iodoacridine-4-carboxamide dihydrochloride salt (9d) From 30d. Yield 69%(2-Diethylaminoethyl)-6-iodoacridine-4-carboxamide dihydrochloride salt (9e). From 30e. Yield 72%; mp 201?203 °CDiethylaminoethyl)-7-iodoacridine-4-carboxamide dihydrochloride salt (9f). From 30f, MHz) d 1.47 400 MHz) d 1.27 (t, 6 H, J = 7 Hz), 3.26 (m, 4H), 3.43 (m, 2H), 4.10 (m, 2H), 7.48 (t, 1H, J = 7.5 Hz), 7.83 (t, 1H, J = 7.5 Hz), 8.27 (d, 1H, J = 8.5 Hz), 8.46 (d, 1H, J = 8 Hz), 8.60 (d, 1H, J = 7 Hz), 8.84 (d, 1H, J = 7 Hz), 9.36 (s, 1H), 10.72 (br s, 1H), 12.27 (br s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.4 (2C) 8.5 Hz), 8.77 (d, 1H, J = 7 Hz), 9.11 (s, 1H), 9.37 (s, 1H), 10.47 (br s, 1H), 11.33 (t, 1H, J = 6 Hz); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.5 (2C), 34.4 Hz), 3.25 (m, 4H), 3.41 (m, 2H), 3.92 (m, 2H), 7.79 (t, 1H, J = 7.5 Hz), 8.19 (d, 1H, J = 9 Hz), 8.36 (d, 1H, J = 9 Hz), 8.41 (d, 1H, J = 8.5 Hz), 8.74 (m, 2H), 9.28 (s, 1H), 10.57 (br s, 1H), 11.32 (br s, 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.5 (2C) 1H); 13 C NMR (DMSO-d 6 , 100 MHz) d 8.5 (2C), pp.134-136, 1560.

1. , J. =. 1h, and J. =. , From 35a. Yield 28%; mp 235?237 °C; IR (KBr) 3500 1150 cm À1 ; MS (base) (br s, 1H); 13 C NMR (DMSO-d 6 , 50 MHz) d 8, 400 MHz) d 1.29 (t, 6H, J = 7 Hz), 3.14 (s, 3H), 3.24 (m, 4H), 3.37 (m, 2H), 3.48 (s, 3H) 8.5 Hz), 8.20 (br s, 1H), 8.85 (s, 1H), 8.89 (br s, 1H), 9.80 (br s, 1H), pp.661-582, 1323.

5. Yield, =. 3h, and J. , ); mp 153?155 °C; IR (KBr) 3353, 3195 1150 cm À1 (br s, 1H), 3H), 4.21 (q, 2H, J = 7 Hz), pp.414-29153, 1337.

6. , J. =. 4h, and J. =. , -carboxamide hydrochloride salt (10d) This compound was prepared from 37 48 and 38 by similar procedure using for 10a?c. Yield 33%; mp 213?215 °C; IR (KBr) 1151 cm À1 ; MS (base), 7 Hz), 3.38 (m, 2H), 3.47 (s, 3H), 3.82 (m, 2H) 1H), 8.19 (d, 1H, J = 8 Hz), 8.28 (d, 1H, J = 8 Hz) 1H), 9.95 (br s, 1H, NH) 1H), pp.3500-3300, 1320.

H. Nmr, 39 (s, 1H); 13 C NMR (CDCl 3 , 100 MHz) d 53, 1H), 7.95 (m, 2H), 7.98 (d, 1H, J = 8 Hz)-(2-Diethylaminoethyl)iodoacridine-9-carboxamides 44a,b Compound 44a, p.20

6. and J. Nmr, From 43b. Yield 57% 99:1, v/v); mp 209?211 °C; IR (KBr) 3500-3300, 2924, 1637 cm À1, MS m/z 573 (M + , 1) (t, 2H, J? 6 Hz), 3.81 (q, 2H, J = 6 Hz), pp.7-9, 1980.

4. , J. =. 1h, and J. =. , From 24f Reaction time at reflux 4 h. The crude product was chromatographed (Al 2 O 3 and EtOAc) Yield 69%; R f = 0.20 (Al 2 O 3 and EtOAc); viscous oil 1150 cm À1 ; ESI-MS m/z 628,2 [M+H] + ; 1 H NMR (CDCl 3, MHz) d 0.88 (t, 9H, J = 7 Hz), 1.05 Hz), 7.37 (d, 1H, J = 8 Hz), 7.52 (br s, 1H), 7.75 (d, 1H, J = 8 Hz), J = 8 Hz), 12.40 (br s, 1H); 13 C NMR (CDCl 3 , 50 MHz) d 9, pp.37-40, 1508.

H. Nmr, From 30d Reaction time at reflux 32 h. The crude product was chromatographed (Al 2 O 3 , EtOAc/pentane, 5:5, v/v) to give in order of elution: stannane 46; yield 25%; R f = 0.79 (Al 2 O 3 , EtOAc/pentane, 5:5, v/v); viscous oil; IR (CCl 4 ) 2959, 2927, 1662, 1286 cm À1 ; ESI-MS m, 6H), 2.76 (m, 4H), 2.88 (m, 2H), 3.73 (m, 2H), pp.59-71, 1945.

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