Table 3.
One-pot synthesis of 2-unsubstituted 3H-imidazole-4-carboxylates 2p–w using benzyamine or allylamine.
| |||||
|---|---|---|---|---|---|
| Entry | DD
|
Imidazole | 2 | Yield[a] (%) | |
| 1 | |||||
| 1 | 1c[b] |
|
|
2p | 69 |
| 2 | 1c[b] |
|
|
2q | 78 |
| 3 | 1d |
|
|
2r | 87 |
| 4 | 1d |
|
|
2s | 81 |
| 5 | 1e |
|
|
2t | 59 |
| 6 | 1e |
|
|
2u | 68 |
| 7 | 1f |
|
|
2v | 57 |
| 8 | 1f |
|
|
2w | 62 |
Isolated yield (after silica gel chromatography) based on starting material, viz. DD 1d–f or the corresponding chlorohydrazone in the case of 1c.
DD 1c was prepared in situ from the parent chlorohydrazone and used without further purification.