Yields of mixed bis-thiopyrrolizidino dispiro-oxindole 6(A-E)(a-b) derived from curcumin, isatins, proline and thioproline.
| Entrya | R1 | R2 | R3 | R4 | R5 | R6 | Product | Yieldb (%) |
|---|---|---|---|---|---|---|---|---|
| 1 | H | H | H | H | OMe | H | 6Aa | 30 |
| 2 | H | H | H | H | OMe | H | 6Ab | 35 |
| 3 | H | F | H | H | I | H | 6Ba | 32 |
| 4 | H | F | H | H | I | H | 6Bb | 37 |
| 5 | H | Cl | H | H | I | H | 6Ca | 31 |
| 6 | H | Cl | H | H | I | H | 6Cb | 35 |
| 7 | H | OMe | H | H | Me | Me | 6Da | 32 |
| 8 | H | OMe | H | H | Me | Me | 6Db | 36 |
| 9 | H | Me | H | H | Me | Me | 6Ea | 31 |
| 10 | H | Me | H | H | Me | Me | 6Eb | 36 |
Unless otherwise noted, the reaction was performed with 1.76 mmol of 3A-E(a) (±), isatins and thioproline in 50.0 mL of MeOH under reflux for 8 h.
Determined after isolation.