Synthesis of substituted dihydrothiophenes 2a–2na.
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Entry | Compd | Ar | R | Yield (%)b |
1 | 2a | p-CH3OC6H4 | Me | 68 |
2 | 2b | m-NO2C6H4 | Me | 55 |
3 | 2c | p-CH3C6H4 | CH2OH | 63 |
4 | 2d | p-CH3OC6H4 | Sec-Bu | 68 |
5 | 2e | p-CH3C6H4 | Sec-Bu | 64 |
6 | 2f | C6H5 | Bn | 48 |
7 | 2g | p-CH3OC6H4 | Bn | 62 (53 : 47) |
8 | 2h | m-CH3OC6H4 | Bn | 60 (51 : 49) |
9 | 2i | o-CH3OC6H4 | Bn | 56 (51 : 49) |
10 | 2j | p-CH3C6H4 | Bn | 55 (52 : 48) |
11 | 2k | p-ClC6H4 | Bn | 53 (53 : 47) |
12 | 2l | p-BrC6H4 | Bn | 55 (53 : 47) |
13 | 2m | p-CH3OC6H4 | CH2CH2Ph | 67 (54 : 46) |
14 | 2n | p-CH3OC6H4 | CH2C6H5OH-p | 57 (55 : 45) |
Reaction conditions: ArCHO (2.0 mmol), CH2(CN)2 (2.0 mmol), α-amino acid ethyl esters (2.0 mmol), 1,3-thiazolidinedione (2.0 mmol), Et3N (3.0 mmol), 40–50 °C, 6 h.
Isolated yields.