Table 3.
Entry | Quinazolin-4(3H)-one | ArOH or RONa | Product | Yield (%) b | |
---|---|---|---|---|---|
1 | 1a | 18 | 75 | ||
2 | 1a | 19 | 52 | ||
3 | 1a | 20 | 73 | ||
4 | 1a | 21 | 51 | ||
5 | 1b | 22 | 53 c | ||
6 | 1f | 23 | 70 | ||
7 | 1g | 24 | 70 | ||
8 | 1a | CH3CH2ONa | 25 | 54 | |
9 | 1b | CH3CH2ONa | 26 | 33 c | |
10 | 1d | CH3CH2ONa | 27 | 67 | |
11 | 1g | CH3CH2ONa | 28 | 64 | |
12 | 1a | CH3CH2CH2ONa | 29 | 48 |
a Reagents and Conditions: 1 (0.5 mmol), HCCP (1.1 equiv.), DIPEA (5.0 equiv.), MeCN (5 mL), rt, activation time (1 h), then phenols (5.0 equiv.), 45 °C, 23 h; or R2ONa (5.0 equiv.), 45 °C, 3 h; b Isolated yield; c Activation time (20 h).