Entry | Acetophenone, 9, R1 | Conditions | Condensation Product | Yield, % | Annulation Product | Yield, % |
1 | 4’-Bromo | 3 M NaOH |
10 | 60 |
20 | 95 |
2 | 3’-Bromo | AcOH, H2SO4 |
11 | 90 |
21 | 97 |
3 | 4’-Chloro | AcOH, H2SO4 |
12 | 64 |
22 | 90 |
4 | 2’-Chloro | AcOH, H2SO4 |
13 | 80 |
23 | 85 |
5 | 3’-Chloro | AcOH, H2SO4 |
14 | 88 |
24 | 95 |
6 | 4’-Nitro | AcOH, H2SO4 |
15 | 57 |
25 | 73 |
7 | 2’-Nitro | AcOH, H2SO4 |
16 | 75 |
26 | 70 |
8 | 3’-Nitro | AcOH, H2SO4 |
17 | 82 |
27 | 60 |