Reaction conditions and yield of products formed in SNAr reactions of 1a with nucleophiles.
| Entry | Compound | Nucleophile | Conditions | Yield [%] |
|---|---|---|---|---|
| 1 | 2a | C6H5SH | TRIS, DMF, rt, 2 h | 87 |
| 2 | 2b | 4-CH3C6H4SH | 89 | |
| 3 | 2c | 3,5-(CH3)2C6H3SH | 81 | |
| 4 | 2d | 4-CH3OC6H4SH | 95 | |
| 5 | 2e | 3-CH3OC6H4SH | 84 | |
| 6 | 2f | 3-NH2C6H4SH | 76 | |
| 7 | 2g | 4-BrC6H4SH | 86 | |
| 8 | 2h | C6H5CH2SH | 65 | |
| 9 | 2i | CH3(CH2)8CH2SH | 37 | |
| 10 | 2j | N-acetyl-l-cysteine methyl ester | 71 | |
| 11 | 2k | CH3NH2 | DMSO, 80 °C, 3 h | 71 |
| 12 | 2l | CH3(CH2)2NH2 | 74 | |
| 13 | 2m | CH3(CH2)3NH2 | 60 | |
| 14 | 2n | CH2 CHCH2NH2 | 65 | |
| 15 | 2o | C6H5CH2NH2 | 63 | |
| 16 | 2p | C6H5OH | K2CO3, DMF, 80 °C, 24 h | 68 |
| 17 | 2q | 4-CH3OC6H4OH | 48 | |
| 18 | 2r | 4-ClC6H4OH | 56 | |
| 19 | 2s | 3-NO2C6H4OH | 48 |