反应详情

To a solution of 5-amino-3-(4-quinolylmethylen) -2-oxindole (431 mg, 1.5 mmol) in DMF (100 ml) containing triethylamine (202 mg, 2 mmol) was added 1-t-butoxycarbonyl-3,3-dimethylthiourea (409 mg, 2 mmol) and HgCl2 (543 mg, 2 mmol). The mixture was stirred at room temperature for 1 h and then filtered on a pad of celite. The residue was washed with ethyl acetate, the organic layer washed several times with water, dried and evaporated to dryness. The residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1. The above obtained BOC-derivative was taken up in trifluoroacetic acid (10 ml) and then stirred for 1 h at room temperature. Ethyl acetate was added, the organic layer washed with 1N sodium hydroxide and brine, dried and evaporated. The residue was chromatographed on a LoBar RP18 column with water as eluant to give pure title compound after freeze-drying. Yield 50% (268 mg).

1. filtrationfiltered on a pad of celite
2. washThe residue was washed with ethyl acetate
3. washthe organic layer washed several times with water
4. customdried
5. customevaporated to dryness
6. customThe residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1
7. customThe above obtained BOC-derivative
8. stirringstirred for 1 h at room temperature
9. washthe organic layer washed with 1N sodium hydroxide and brine
10. customdried
11. customevaporated
12. customThe residue was chromatographed on a LoBar RP18 column with water as eluant