Table 2.
Nucleophilic substitution of 6-fluoroquinoxalines with amines and nitrogen-containing aromatic heterocycles.
| Entry | Compound | R1 | NR2R3 | Yield (%)a |
|---|---|---|---|---|
| 1 | 3 | H | Pyrrolidine | 93 |
| 2 | 4 | H | Piperidine | 85 |
| 3 | 5 | H | 4-Methoxybenzylamine | 45 |
| 4 | 6 | H | Imidazole | 92b |
| 5 | 7 | H | Pyrazole | 88b |
| 6 | 8 | Methyl | Pyrrolidine | 88c |
| 7 | 9 | Methyl | Piperidine | 50c |
| 8 | 10 | Methyl | Imidazole | 88 |
| 9 | 11 | Methyl | Pyrazole | 88 |
| 10 | 12 | 2-Furyl | Pyrrolidine | 93 |
| 11 | 13 | 2-Furyl | Piperidine | 90 |
| 12 | 14 | 2-Furyl | Homopiperidine | 73 |
| 13 | 15 | 2-Furyl | 4-Methoxybenzylamine | 80 |
| 14 | 16 | 2-Furyl | Pyrrole | 94 |
| 15 | 17 | 2-Furyl | Imidazole | 97 |
| 16 | 18 | 2-Furyl | Pyrazole | 97 |
| 17 | 19 | 4-Methylphenyl | Pyrrolidine | 90c |
| 18 | 20 | 4-Methylphenyl | Homopiperidine | 50c |
| 19 | 21 | 4-Methylphenyl | Pyrrole | 96 |
| 20 | 22 | 4-Methylphenyl | Pyrazole | 96 |
a Isolated yields of pure compounds.
b Microwave irradiation, 200 oC, 5 min
c Microwave irradiation, 200 oC, 60 min