Synthetic method of quinazolinone compounds
A quinazolinone and a synthesis method technology, applied in the field of organic synthesis, can solve the problems of affecting medicinal properties, harmful transition metal environment, and high cost of a catalytic system, and achieve the effects of mild reaction conditions, cheap raw materials, and high selectivity and yield.
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Synthetic example 1
[0025] Synthesis of 2-methylquinazolin-4(3H)-one
[0026] Add 0.5 mmol anthranilamide to the reaction vessel, vacuumize, backfill with oxygen, then add 50 mol% acetic acid, 1 ml 1,4-dioxane, 1.0 mmol triethylamine, seal; heat to 120 o C for 10 hours. After the reaction solution was cooled to room temperature, it was washed with water or a saturated saline solution, then extracted with an organic solvent, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 90%. No catalyst residue was detected by NMR. 1 H NMR (400 MHz, CDCl 3 , TMS): δ 12.23 (s, 1H, NH), 8,28 (d, J = 8.0Hz, 1H, ArH), 7.79 (t, J = 7.6Hz, 1H, ArH), 7.68 (d, J = 8.0Hz, 1H, ArH), 7.48 (t, J = 7.6Hz, 1H, ArH), 2.62 (s, 3H, CH 3 ); 13 C NMR (100 MHz, CDCl 3 , TMS): δ 164.5, 153.4,. 149.4, 134.9, 127.0, 126.4, 126.2, 120.2, 22.1.
Synthetic example 2
[0028] Synthesis of 2-ethylquinazolin-4(3H)-one
[0029] Add 0.5 mmol anthranilamide and 20 mol% benzenesulfonic acid to the reaction vessel, vacuumize, backfill with oxygen, then add 1 ml N,N-dimethylformamide, 0.5 mmol tri-n-propylamine, seal; heat to 110 o C for 12 hours. After the reaction solution was cooled to room temperature, it was washed with water or a saturated saline solution, then extracted with an organic solvent, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 78%. No catalyst residue was detected by NMR. 1 H NMR (400 MHz, CDCl 3 , TMS): δ 11.96 (s, 1H, NH), 8,32 (q, J = 4.0Hz, 1H, ArH), 7.78-7.81 (m, 1H, ArH), 7.71 (q, J = 6.8Hz, 1H, ArH), 7.46-7.50 (m, 1H, ArH), 2.87 (q, J = 7.2Hz, 2H, CH 2 ,), 1.46 (t, J = 7.2Hz, 3H, CH 3 , ); 13 C NMR (100 MHz, CDCl 3 , TMS): δ 164.4, 157.7, 149.5, 134.8, 127.2, 126.4, 126.3, 120.5, 29.2, 11.6....
Synthetic example 3
[0031] Synthesis of 2-Propylquinazolin-4(3H)-one
[0032] Add 0.5 mmol anthranilamide and 40 mol% benzoic acid into the reaction vessel, vacuumize, backfill with oxygen, then add 1 ml dimethyl sulfoxide, 0.7 mmol tri-n-butylamine, seal; heat to 125 o C for 15 hours. After the reaction solution was cooled to room temperature, it was washed with water or a saturated saline solution, then extracted with an organic solvent, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 75%. No catalyst residue was detected by NMR. 1 H NMR (400 MHz, CDCl 3 , TMS): δ 12.18 (s, 1H, NH), 8,28-8.30 (m, 1H, ArH), 7.75-7.79 (m, 1H, ArH), 7.71 (d, J = 8.0Hz, 1H, ArH ), 7.47 (t, J = 7.6Hz, 1H, ArH), 2.79 (t, J = 7.2Hz, 2H, CH 2 ); 1.89-1.98 ( m, 2H,CH 2 ), 1.08 (t, J = 7.2Hz, 3H, CH 3 ). 13 C NMR (100 MHz, CDCl 3 , TMS): δ164.5, 156.9, 149.5, 134.8, 127.2, 126.3, 126.2, 120....
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