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. 2021 Dec 1;11(61):38712–38716. doi: 10.1039/d1ra08469k

Synthesis of α-cyano tetrahydroisoquinolines with a quaternary center via Strecker reactiona.

graphic file with name d1ra08469k-u2.jpg
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)
a

Reaction conditions: 1 (0.5 mmol), TMSCN (1.0 mol), KF (1.0 mol), Na2CO3 (0.25 mmol), 3 mL of ClCH2CH2Cl, 48 h.

b

Isolated yield.