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. 2024 Nov 6;29(22):5255. doi: 10.3390/molecules29225255

Table 1.

Screening of the thiol-involved cascade reaction a.

graphic file with name molecules-29-05255-i001.jpg
Entry Base (eq.) Solvent Temp. (°C) Time (min) 3a (%) b
1 K2CO3 (0.6) neat 25 60 30
2 K2CO3 (0.6) H2O 25 60 49
3 K2CO3 (0.6) EtOH 25 60 31
4 K2CO3 (0.6) EtOH/H2O 25 60 78
5 K2CO3 (0.6) EtOH/H2O 50 60 96
6 K2CO3 (0.6) EtOH/H2O 50 20 95
7 NaOH (1.2) EtOH/H2O 50 20 94
8 Na2CO3 (0.6) EtOH/H2O 50 20 94
9 NaHCO3 (1.2) EtOH/H2O 50 20 92
10 Et3N (1.2) EtOH/H2O 50 20 94
11 DBU (1.2) EtOH/H2O 50 20 94
12 K2CO3 (0.6) Acetone 50 20 91
13 K2CO3 (0.5) EtOH/H2O 50 20 92
14 K2CO3 (0.75) EtOH/H2O 50 20 95
15 c K2CO3 (0.6) EtOH/H2O 50 5 99
16 c K2CO3 (0.6) EtOH/H2O 80 5 95
17 d K2CO3 (0.6) EtOH/H2O 50 5 98

a Reaction conditions: 1a (0.2 mmol), 2a (0.2 mmol), the loading of base based on 1a. EtOH (1 mL), H2O (1 mL); b isolated yields; c MW, 20 W; d using 3-iodopropyl isothiocyanate, MW, 20 W.