Optimization of reaction conditionsa.
| |||
|---|---|---|---|
| S. no. | Pd(OAc)2 | PTSA (equiv.) | Yieldsb (%) |
| 1 | 10 mol% | 0.75 | 60 |
| 2 | 10 mol% | 1.0 | 56 |
| 3 | 10 mol% | 0.25 | 69 |
| 4 | 15 mol% | 0.25 | 46 |
| 5 | 7.5 mol% | 0.25 | 69 |
| 6 | 5 mol% | 0.25 | 74 |
| 7 | 3 mol% | 0.25 | 70 |
| 8 | 5 mol% | 0.25 | 64c |
| 9 | 5 mol% | 0.25 | 70d |
| 10 | 5 mol% | 0.25 | 61e |
| 11 | 5 mol% | 0.25 | 62f |
| 12 | 5 mol% | 0.25 | 84 g |
| 13 | 5 mol% | 0.25 | 65h |
| 14 | 5 mol% | 0.25 | 70i |
Reagents and conditions: a mixture of 3-phenyl-2H-benzo[b][1,4]oxazin-2-one (1a, 1 equiv.), NBS (2a, 1.2 equiv.), Pd(OAc)2 and PTSA as indicated in the parenthesis were irradiated with microwave under indicated solvent at indicated temperature for given period of time in sealed reaction vial.
Isolated yields.
Reaction mixture was irradiated at 110 °C for 15 minutes.
Reaction mixture was irradiated at 90 °C for 30 minutes.
Reaction was irradiated at 80 °C for 30 minutes.
Reaction was irradiated at 100 °C for 25 minutes.
Reaction was irradiated at 100 °C for 15 minutes.
Reaction was irradiated at 100 °C for 10 minutes.
Reaction was carried out at 100 °C under conventional heating for 1 hour.