Table 3. Synthesis of 4H-pyran and -chromene derivatives 6a–i, 7a–f and 8a–f catalyzed by Arg@ZY-Fe3O4 under the optimized reaction conditionsa.
| |||||||
|---|---|---|---|---|---|---|---|
| Entry | R1 | R2 | Product | Time (min) | Yielda (%) | M.p. (°C) (lit.) | AEfb (%)/E-factor |
| 1 | Resorcinol | H | 6a | 5 | 97 | 238–239 (230–231)52 | 93.6/0.07 |
| 2 | Resorcinol | 4-Cl | 6b | 7 | 93 | 155–156 (160–162)52 | 93.6/0.07 |
| 3 | Resorcinol | 2,4-Cl | 6c | 9 | 91 | 252–254 (257–259)46 | 93.6/0.08 |
| 4 | Resorcinol | 2-NO2 | 6d | 7 | 92 | 176–178 (160–162)46 | 93.6/0.07 |
| 5 | Resorcinol | 3-NO2 | 6e | 8 | 95 | 174–176 (170–172)55 | 93.6/0.07 |
| 6 | Resorcinol | 4-NO2 | 6f | 5 | 99 | 165–167 (168–170)46 | 93.6/0.07 |
| 7 | Resorcinol | 4-CH3 | 6g | 12 | 91 | 188–190 (182–183)52 | 93.6/0.08 |
| 8 | Resorcinol | 4-OCH3 | 6h | 14 | 90 | 190–192 (111–113)52 | 93.6/0.08 |
| 9 | Resorcinol | 3,4-OCH3 | 6i | 12 | 88 | 152–154 (148–150)61 | 93.6/0.08 |
| 10 | Dimedone | H | 7a | 7 | 95 | 227–229 (230–231)55 | 94.2/0.06 |
| 11 | Dimedone | 2-Cl | 7b | 9 | 93 | 192–194 (195–197)55 | 94.2/0.07 |
| 12 | Dimedone | 2,4-Cl | 7c | 10 | 95 | 192–194 (190–191)55 | 94.2/0.06 |
| 13 | Dimedone | 2-NO2 | 7d | 7 | 96 | 241–243 (230–232)54 | 94.2/0.06 |
| 14 | Dimedone | 4-NO2 | 7e | 5 | 99 | 190–191 (178–180)54 | 94.2/0.06 |
| 15 | Dimedone | 4-OCH3 | 7f | 12 | 91 | 188–190 (201–203)55 | 94.2/0.07 |
| 16 | 2-Naphthol | H | 8a | 12 | 90 | 287–289 (281–283)61 | 94.3/0.07 |
| 17 | 2-Naphthol | 2-Cl | 8b | 11 | 92 | 266–268 (270–271)55 | 94.3/0.07 |
| 18 | 2-Naphthol | 3-NO2 | 8c | 10 | 92 | 238–240 (238–240)55 | 94.3/0.07 |
| 19 | 2-Naphthol | 4-NO2 | 8d | 9 | 97 | 186–188 (184–185)55 | 94.3/0.06 |
| 20 | 2-Naphthol | 4-OCH3 | 8e | 14 | 89 | 171–173 (188–189)55 | 94.3/0.07 |
| 21 | 2-Naphthol | 3,4-OCH3 | 8f | 11 | 90 | 187–189 (195–196)62 | 94.3/0.07 |
Pure product isolated.
Atom economy of efficiency.