Synthesis method of pyrrole [1, 2-a] quinoline derivative
A synthesis method and derivative technology, applied in the field of synthesis of pyrrolo[1,2-a]quinoline derivatives, can solve the problems of limited universality of reactants, cumbersome synthesis steps, rare compounds, etc. The treatment process is simple, the synthesis process is simple, and the effect of shortening the reaction process
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Embodiment 1
[0041] Weigh 1.0mmol, 229mg of 2-propionyl-3-anilino-4-methylcyclobutenone 1a, 1mmol, 0.08mL of 3-bromopropyne, 2.0mmol, 80mg of sodium hydroxide in a 25mL round bottom In the flask, add 10mL acetonitrile subsequently, stir 8 hours at 80 ℃, TLC monitors reaction progress, until reactant disappears; After reaction finishes, reaction solution is poured in the saturated sodium chloride solution of 20mL, extracts three times with dichloromethane (3× 20mL), liquid separation, combined organic phase; organic phase with anhydrous Na 2 SO 4After drying, the solvent was evaporated under reduced pressure. Finally, petroleum ether and acetone were used as developing solvents, and column chromatography separated to obtain 254 mg of the target compound 2a as a white solid with a yield of 95%.
[0042] The specific reaction formula is:
[0043]
[0044] White solid (95% yield); 1 H NMR (400MHz, CDCI 3 )δ: 1.50(t, J=8.0Hz, 3H), 3.31(q, J=6.5Hz, 2H), 2.58(s, 3H), 2.62(s, 3H), 6.57(s, 1...
Embodiment 2
[0046] Weigh 1.0mmol, 231mg of 2-methoxycarboxy-3-anilino-4-methylcyclobutenone 1b, 1mmol, 0.08mL of 3-bromopropyne, 2mmol, 0.224mg of potassium tert-butoxide in In a 25mL round bottom flask, add 10mL N,N-dimethylformamide, stir at 70°C for 7 hours, monitor the reaction progress by TLC until the reactant disappears; after the reaction, pour the reaction solution into 30mL saturated sodium chloride solution , extracted three times with dichloromethane (3×20mL), separated the layers, back-extracted the organic phase twice with distilled water (20×2mL), combined the organic phases; used anhydrous MgSO 4 After drying, the solvent was evaporated under reduced pressure and separated by column chromatography to obtain 261 mg of the target compound 2b as a white solid with a yield of 97%.
[0047] The specific reaction formula is:
[0048]
[0049] White solid (97% yield); 1 H NMR (400MHz, CDCI 3 )δ: 2.68(s, 3H), 2.74(s, 3H), 4.06(s, 3H), 7.08(s, 1H), 7.21(d, J=7.5Hz, 1H), 6.97(...
Embodiment 3
[0051] Weigh 1.0mmol, 215mg of 2-acetyl-3-anilino-4-methylcyclobutenone 1c, 1mmol, 0.08mL of 3-chloropropyne, 2.0mmol, 48mg of sodium hydride in a 25mL round bottom In the flask, add 10mL tetrahydrofuran subsequently, stir at 60 ℃ for 8 hours, TLC monitors the reaction process, until the reactant disappears; After the reaction, the reaction solution is poured into 25mL of saturated sodium chloride solution, extracted three times with dichloromethane (3× 20mL), liquid separation, combined organic phase; organic phase with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure. Finally, petroleum ether and acetone were used as developing solvents, and column chromatography separated to obtain 238 mg of the target compound 2c as a white solid with a yield of 94%.
[0052] The specific reaction formula is:
[0053]
[0054] White solid (94% yield); 1 H NMR (400MHz, CDCI 3 )δ: 2.43(s, 3H), 2.47(s, 3H), 2.56(s, 3H), 7.11(d, J=7.5Hz, 1H), 7.15(s, 1...
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