Table 1. Optimization of Reaction Conditions for the Sonochemical Synthesis of 3-Hydroxy-5,5-dimethyl-2-(2-phenylimidazo[1,2-a]pyridin-3-yl)cyclohex-2-enone 4(a)a.
| entry | source of iodine | solvent | time (h)b | yieldc |
|---|---|---|---|---|
| 1 | − | − | 2 | NR |
| 2 | − | H2O | 2 | NR |
| 3 | NaI | H2O | 1 | 28 |
| 4 | KI | H2O | 1 | 33 |
| 5 | CuI | H2O | 1 | 55 |
| 6 | ZnI2 | H2O | 1 | 47 |
| 7 | I2 (15 mol %) | − | 1.5 | 62 |
| 8 | I2 (15 mol %) | H2O | 1 | 79 |
| 9 | I2(20mol %) | H2O | 1 | 84 |
| 10 | I2 (20 mol %) | H2O | 1.5 | 84 |
| 11 | I2 (25 mol %) | H2O | 1 | 83 |
Reaction conditions: 2-aminopyridine (1 mmol) 1(a), acetophenone (1 mmol) 2(a), and dimedone (1 mmol) (3).
All the reactions were monitored by TLC.
Isolated yield.