Table 2. Aza-Prins Reaction of 1 with Isatin Derivatives.
| entry | isatin | time (h) | product | yield (%) |
|---|---|---|---|---|
| 1 | R = H (5a) | 22 | 6a | 70 |
| 2 | R = 5-NO2 (5b) | 13 | 6b | 69 |
| 3 | R = 5-CF3O (5c) | 8 | 6c | 63 |
| 4 | R = 5-F (5d) | 46 | 6d | 67 |
| 5 | R = 5-Br (5e) | 16 | 6e | 74 |
| 6 | R = 5-MeO (5f) | 40 | 6f | 33 |
| 7 | R = 1-Me (5g) | 40 | 6g | 82 |
| 8a | R = 6-Cl (5h) | 22 | 6h | 50 |
| 9 | R = 7-Cl (5i) | 19 | 6i | 69 |
| 10a | R = 4-Cl (5j) | 72 | 6j | 0 |
| 11 | R = 6-CF3 (5k) | 17 | 6k | 66 |
| 12 | R = 6-CH3O (5l) | 43 | 6l | 3.4 |
4 M HCl/dioxane was used as the acid.
