Synthesis of α-cyano tetrahydroisoquinolines with a quaternary center via Strecker reactiona.
Entry | R1/R2 | R3/X | R | Yieldb (%) |
---|---|---|---|---|
1 | H/H | CH3/I | C6H5 | 93 (2a) |
2 | H/H | CH3/I | 2-CH3C6H4 | 85 (2b) |
3 | H/H | CH3/I | 3-CH3C6H4 | 99 (2c) |
4 | H/H | CH3/I | 4-CH3C6H4 | 94 (2d) |
5 | H/H | CH3/I | 4-FC6H4 | 88 (2e) |
6 | H/H | CH3/I | 4-ClC6H4 | 94 (2f) |
7 | H/H | CH3/I | 4-CH3OC6H4 | 92 (2g) |
8 | H/CH3 | CH3/I | C6H5 | 95 (2h) |
9 | CH3/CH3 | CH3/I | C6H5 | 93 (2i) |
10 | H/CH3O | CH3/I | C6H5 | 86 (2j) |
11 | H/H | CH3/I | CH3 | 87 (2k) |
12 | H/H | Et/I | C6H5 | 85 (2l) |
13 | H/H | CH3(CH2)9/I | C6H5 | 80 (2m) |
14 | H/H | Bn/Br | C6H5 | 85 (2n) |
Reaction conditions: 1 (0.5 mmol), TMSCN (1.0 mol), KF (1.0 mol), Na2CO3 (0.25 mmol), 3 mL of ClCH2CH2Cl, 48 h.
Isolated yield.