Table 1.
Optimization of reaction conditions for the synthesis of dye 1.
Entry | Oxidant | Base | Yield, %a |
1 | p-chloranil | Et3N | 29 |
2 | DDQ | Et3N | 7 |
3 | Ce(NH4)2(NO3)6 | Et3N | 0 |
4 | Ce(NH4)2(NO3)6 | DBU | 8 |
5 | p-chloranil | DBU | 24b |
6 | p-chloranil | K2CO3 | 0 |
7 | p-chloranil | NaOH | 0 |
aIsolated yield, after column chromatography; byields varied from 8 to 24%.