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. 2018 Jun 20;8(40):22498–22505. doi: 10.1039/c8ra03605e

Synthesis of substituted dihydrothiophenes 2a–2na.

graphic file with name c8ra03605e-u2.jpg
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)
a

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.

b

Isolated yields.