Table 1. Chemical, Physical, and Analytical Data of Derivatives 9a−h and 10a−i.
| compd | R6 | R7 | R8 | mp (°C) | recryst solventa | yield (%) | analysis |
|---|---|---|---|---|---|---|---|
| 9ab | H | H | H | 242−244 | a | 56 | C, H, N (C11H9NO2) |
| 9b | F | H | H | >300 | b | 29 | C, H, N, F (C11H8FNO2) |
| 9c | H | F | H | 270−271 | c | 41 | C, H, N, F (C11H8FNO2) |
| 9d | H | H | F | 268−270 | b | 40 | C, H, N, F (C11H8FNO2) |
| 9eb | Cl | H | H | >300 | b | 29 | C, H, N, Cl (C11H8ClNO2) |
| 9fb | H | Cl | H | >300 | b | 96 | C, H, N, Cl (C11H8ClNO2) |
| 9gb | H | H | Cl | >300 | b | 55 | C, H, N, Cl (C11H8ClNO2) |
| 9h | Cl | Cl | H | 114−115 | d | 19 | C, H, N, Cl (C11H7Cl2NO2) |
| 10a | H | H | H | 213−214 | d | 65 | C, H, N, F (C18H14FNO2) |
| 10b | F | H | H | 234−235 | e | 94 | C, H, N, F (C18H13F2NO2) |
| 10c | H | F | H | 186−187 | e | 100 | C, H, N, F (C18H13F2NO2) |
| 10d | H | H | F | 193−194 | f | 78 | C, H, N, F (C18H13F2NO2) |
| 10e | Cl | H | H | 214−216 | e | 92 | C, H, N, Cl, F (C18H13ClFNO2) |
| 10f | H | Cl | H | 185−187 | e | 73 | C, H, N, Cl, F (C18H13ClFNO2) |
| 10g | H | H | Cl | 215−217 | g | 92 | C, H, N, Cl, F (C18H13ClFNO2) |
| 10h | Cl | Cl | H | 235−237 | d | 49 | C, H, N, Cl, F (C18H12Cl2FNO2) |
| 10i | H | 1-pyrrolidinyl | H | 175−177 | e | 56 | C, H, N, F (C22H21FN2O2) |
Recrystallization solvents: (a) aceton, (b) ethanol, (c) isopropanol, (d) toluene, (e) toluene/cyclohexane, (f) benzene/cyclohexane, (g) benzene.
Reference (17).