Table 2. Scope of different aryl aldehyde and malononitrile for the synthesis of benzylidene derivativesa.
| ||||||
|---|---|---|---|---|---|---|
| Entry | R | Timeb (min) | Product | Yieldc (%) | M.P. (°C) (observed) | M.P. (°C) (reported) |
| 1 | –C6H5 | 15 | 1a | 95 | 83–85 | 81–83 (ref. 40) |
| 2 | 4-FC6H4 | 20 | 1b | 83 | 124–126 | 130 (ref. 41) |
| 3 | 4-ClC6H4 | 20 | 1c | 89 | 158–160 | 160–162 (ref. 40) |
| 4 | Furfural | 25 | 1d | 92 | 72–75 | 70 (ref. 42) |
| 5 | 4-MeC6H4 | 20 | 1e | 95 | 134–136 | 132–134 (ref. 40) |
| 6 | 2,5-(OMe)2C6H3 | 25 | 1f | 85 | 109–111 | 110–112 (ref. 43) |
| 7 | 3-MeC6H4 | 25 | 1g | 90 | 75–77 | 74–75 (ref. 44) |
| 8 | 4-BrC6H4 | 20 | 1h | 90 | 152–154 | 153–154 (ref. 40) |
| 9 | 4-OMeC6H4 | 20 | 1i | 92 | 121–123 | 122 (ref. 41) |
| 10 | 4-NO2C6H4 | 20 | 1j | 86 | 159–161 | 158–160 (ref. 43) |
| 11 | 2,4,5-(OMe)3C6H2 | 30 | 1k | 88 | 134–136 | 136 (ref. 41) |
| 12 | 1-Naphthayl | 50 | 1l | 82 | 173–175 | 174–176 (ref. 44) |
| 13 | 4-CNC6H4 | 10 | 1m | 94 | 152–154 | 151–153 (ref. 44) |
Reaction condition: aldehyde (1 mmol), malononitrile (1 mmol), SMA (1 mol%).
Reaction progress monitored by TLC.
Isolated yield.