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. 2018 Apr 3;8(23):12635–12640. doi: 10.1039/c8ra01236a

Substrate scope of 1 and synthesis of target molecules 3a.

graphic file with name c8ra01236a-u2.jpg
Entry 1 (R/R1) 2 (R2) 3 Yieldb (%)
1 1a (4-FC6H5/CH3) 2a (4-ClC6H5) 3a 66
2 1a (4-FC6H5/CH3) 2b (C6H5) 3b 58
3 1b (3-FC6H5/CH3) 2b (C6H5) 3c 62
4 1c (3-ClC6H5/CH3) 2a (4-ClC6H5) 3d 63
5 1c (3-ClC6H5/CH3) 2b (C6H5) 3e 68
6 1d (4-BrC6H5/CH3) 2a (4-ClC6H5) 3f 65
7 1d (4-BrC6H5/CH3) 2b (C6H5) 3g 62
8 1e (3-BrC6H5/CH3) 2b (C6H5) 3h 60
9 1f (C6H5/CH3) 2a (4-ClC6H5) 3i 65
10 1f (C6H5/CH3) 2b (C6H5) 3j 63
11 1f (C6H5/CH3) 2c (4-OCH3C6H5) 3k 64
12 1g (3-CH3C6H5/CH3) 2b (C6H5) 3l 62
13 1h (n-butyl/CH3) 2a (4-ClC6H5) 3m 70
14 1i (4-ClC6H5/H) 2a (4-ClC6H5) 3n 71
15 1j (3-ClC6H5/H) 2a (4-ClC6H5) 3o 72
16 1k (3-BrC6H5/H) 2c (4-OCH3C6H5) 3p 68
17 1l (4-CH3C6H5/H) 2a (4-ClC6H5) 3q 60
18 1a (4-FC6H5/CH3) 2d (n-propyl) 3r 62
a

The reaction was performed with 1 (1.0 mmol), 2 (0.6 mmol), and p-TSA (0.3 mmol) in EtOH (15 mL) at reflux for 3 hours.

b

Isolated yields based on enaminones 1.