Spirooxindoles obtained with pre-synthesized acyl chloridea.
| Compound # | R1 | R2 | R3 | a/b | Yield,% |
|---|---|---|---|---|---|
| 22a,b | H | 4F | 4-Cl | 1/2 | 64 |
| 23a,b | H | 4-Cl | 4-Cl | 1/2 | 53 |
| 24a,b | H | 4-Br | 4-Cl | 1/2 | 49 |
| 25a,b | H | 4-OH | 4-Cl | 1/2 | 62 |
| 26a,b | H | 4-OEt | 4-Cl | 1/5 | 57 |
| 27a,b | H | 3-Cl, 4-F | 4-Cl | 2/5 | 55 |
| 28b | H | 2-F | 4-Cl | — | 44 |
Reaction conditions: Schiff base (1.0 eq.), 4-chlorophenylacetyl chloride (1.5 eq.), Et3N (3.0 eq.), DMF, reflux for 6–9 h.