Synthesis of 2,3-dihydroquinazolin-4(1H)-ones using UiO-66-NH2-MOF@COF as a catalysta.
| Entry | R | Amine (ArNH2 or NH4OAC) | Product | Time (min) | Yieldb (%) | M.p. °C | Lit. M.p. oC |
|---|---|---|---|---|---|---|---|
| 1 | H | Ph | 4a | 20 | 91 | 213–215 | 214–216 (ref. 56) |
| 2 | 4-Me | Ph | 4b | 14 | 85 | 211–213 | 213–214 (ref. 57) |
| 3 | 4-OMe | Ph | 4c | 15 | 89 | 202–204 | 205–207 (ref. 33) |
| 4 | 4-Cl | Ph | 4d | 16 | 94 | 220–223 | 222–224 (ref. 33) |
| 5 | 3-NO2 | Ph | 4e | 12 | 92 | 183–185 | 186–188 (ref. 57) |
| 6 | 4-NO2 | Ph | 4f | 10 | 98 | 192–194 | 195–197 (ref. 57) |
| 7 | 4-Me | 4-MeC6H4 | 4g | 25 | 90 | 244–246 | 243–247 (ref. 58) |
| 8 | 4-OMe | 4-ClC6H4 | 4h | 18 | 87 | 243–245 | 244–247 (ref. 59) |
| 9 | 4-F | 4-Me | 4i | 17 | 93 | 240–242 | 241–243 (ref. 59) |
| 10 | 4-Cl | 5-Cl, 2-OHC6H3 | 4j | 10 | 89 | 233–236 | 235–237 (ref. 58) |
| 11 | 2,6-Cl2 | Ph | 4k | 14 | 93 | 231–232 | 234–236 (ref. 57) |
| 12 | 4-Br | Ph | 4l | 16 | 96 | 218–220 | 221–223 (ref. 57) |
| 13 | 4-SMe | 4-BrC6H4 | 4m | 25 | 94 | 246–248 | —c |
| 14 | 3-NO2 | NH4OAC | 6a | 20 | 91 | 184–186 | 186–188 (ref. 33) |
| 15 | 2-Cl | NH4OAC | 6b | 15 | 96 | 202–204 | 203–205 (ref. 56) |
| 16 | 4-OH, 3-OMe | NH4OAC | 6c | 25 | 87 | 223–225 | 226–227 (ref. 33) |
| 17 | H | NH4OAC | 6d | 20 | 91 | 222–224 | 225–226 (ref. 57) |
| 18 | 4-OMe | NH4OAC | 6e | 17 | 93 | 187–189 | 192–193 (ref. 57) |
| 19 | 4-Me | NH4OAC | 6f | 19 | 89 | 230–232 | 233–234 (ref. 57) |
| 20 | 4-SMe | NH4OAC | 6g | 20 | 87 | 235–237 | —c |
Reaction conditions: UiO-66-NH2-MOF@COF (0.007 g), isatoic anhydride, aldehyde, aryl amine or NH4OAc (1 : 1 : 1 molar ratio) under free solvent conditions.
Isolated yield.
New products.