Table 2.
Preparation of benzisoxazolo[2,3-a]pyridinium tetrafluoroborates (1)a
![]() | |||
|---|---|---|---|
| Entry | Acetanilide (4) | Product (1) | % Yieldb |
| 1 | 4a |
![]() 1a |
72 |
| 2 | 4b |
![]() 1b |
77 |
| 3 | 4c |
![]() 1c |
83 |
| 4 | 4d |
![]() 1d |
79 |
| 5 | 4e |
![]() 1e |
80 |
| 6 | 4f |
![]() 1f |
71 |
| 7 | 4g |
![]() 1g |
76 |
| 8 | 4h |
![]() 1h |
74 |
Hydrolysis: 4 (1.0 mmol), HBF4 (50% aqueous solution, 1.2 mmol), water (1 mL), were refluxed until hydrolysis was complete. Diazotization/cyclization: the preceding mixture was evaporated in vacuo and dissolved in CH3CN (8 mL). tBuONO (1.2 mmol) was added. Mixture was stirred 1 hr at RT, then heated to reflux.
Isolated yields; average of at least 2 runs.








