Table 4. Synthesis of Isoindolo[2,1-b]isoquinolin-5(7H)-ones.
| entry | R1 | R2 | R3 | R4 | yield 10a–f (%)a | yield 11a–f (%)a | yield 12a–f (%)a | yield 13a–f (%)a |
|---|---|---|---|---|---|---|---|---|
| 1 | H | H | H | H | 72 (10a) | 60 (11a) | 63 (12a) | 91 (13a) |
| 2 | F | H | H | H | 68 (10b) | 26 (11b) | 80 (12b) | 83 (13b) |
| 3 | H | F | H | H | 59 (10c) | 16 (11c) | 58 (12c) | 74 (13c) |
| 4 | Cl | H | H | H | 51 (10d) | 23 (11d) | 62 (12d) | 96 (13d) |
| 5 | Me | H | H | H | 67 (10e) | 68 (11e) | 59 (12e) | 92 (13e) |
| 6 | OMe | H | H | H | 62 (10f) | 64 (11f) | 69 (12f) | 45 (13f)b |
| 7 | H | H | H | F | 55 (10g) | 45 (11g) | 74 (12g) | 99 (13g) |
| 8 | H | H | Me | H | 75 (10h) | 92 (11h) | 66 (12h) | 82 (13h) |
a
Yield of pure products after flash column chromatography purification.
b
Addition of the NaI/DBU system was not necessary for performing the elimination step.