Table 3. Substrate Scope for Several Chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-one Derivatives 8a-qa.
| entry | substituent (R) | product | time (h) | yieldb (%) | melting
point (°C) |
|
|---|---|---|---|---|---|---|
| determined | reported47,48 | |||||
| 1 | C6H5 | 8a | 2.5 | 93 | 206–208 | 211–212 |
| 2 | 2-ClC6H4 | 8b | 6 | 78 | 238–240 | 242–244 |
| 3 | 3-ClC6H4 | 8c | 4.5 | 84 | 179–181 | 177–178 |
| 4 | 4-ClC6H4 | 8d | 3.5 | 92 | 236–238 | 255–257 |
| 5 | 3-OHC6H4 | 8e | 5.5 | 71 | 147–149 | new |
| 6 | 4-OHC6H4 | 8f | 3.5 | 94 | 156–158 | 157–158 |
| 7 | 4-CH3C6H4 | 8g | 4 | 92 | 225–227 | 229–230 |
| 8 | 3-FC6H4 | 8h | 5 | 75 | 201–203 | new |
| 9 | 4-FC6H4 | 8i | 2.5 | 94 | 218–220 | 224–225 |
| 10 | 4-OCH3C6H4 | 8j | 4 | 89 | 223–225 | 206–207 |
| 11 | 3-BrC6H4 | 8k | 7 | 80 | 205–207 | new |
| 12 | 4-BrC6H4 | 8l | 2 | 91 | 235–237 | 240–242 |
| 13 | 2-furyl | 8m | 6 | 87 | 171–173 | 175–176 |
| 14 | 4-CNC6H4 | 8n | 4 | 93 | 218–220 | 228–229 |
| 15 | 3,4-(OCH3)2 C6H3 | 8o | 4 | 85 | 208–210 | 215–216 |
| 16 | 3,4-(OH)2C6H3 | 8p | 8 | 92 | 177–179 | 180–181 |
| 17 | 4-N(CH3)2C6H4 | 8q | 10 | 84 | 181–183 | 182–183 |
| 18 | acetaldehyde | 18 | n.r. | |||
| 19 | propionaldehyde | 18 | n.r. | |||
| 20 | butyraldehyde | 18 | n.r. | |||
One-pot reaction performed using 5 (1 equiv), 6 (1 equiv), and 7 (1 equiv) at room temperature in aq. EtOH (1:1). 5 mol % catalyst.
Yield of the isolated product. n.r.—no reaction
