Synthesis method of benzolactam compound
A technology of benzolactam and synthesis method, applied in the direction of organic chemistry and the like, can solve the problem of high C-N bond dissociation energy, and achieve the effects of high chemical and regioselectivity, high synthesis efficiency and mild reaction conditions
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Embodiment 1
[0024] Example 1: 8-Hydroxy-1-methyl-5,6-dihydrobenzo[b]azooctane-2,4(1H,3H)-dione
[0025]
[0026] Add hydroquinone (55 mg, 0.5 mmol) into a 10 mL reaction tube, N - A mixed solvent of methyl-4-piperidone (86 mg, 0.75 mmol), photosensitizer iron phthalocyanine (II) (11.4 mg, 2 mmol %), acetic acid (1 mL) and water (2ml). The reaction mixture was allowed to react for 36 h under an oxygen atmosphere at room temperature under a 5 W white LED light. Upon completion, the reaction mixture was washed with NaHCO 3 The aqueous solution was quenched, then ethyl acetate (10 mL) was added to dissolve the reaction system, and the reaction system was washed with water (2×10 mL) and brine (10 mL) successively. The aqueous phase was further extracted with ethyl acetate (10 mL) and washed as before. The combined organic phases were washed with anhydrous Na 2 SO 4 Dried and concentrated. Purified by silica gel column chromatography, 8-hydroxy-1-methyl-5,6-dihydrobenzo[b]azooctane-2,4...
Embodiment 2
[0028] Example 2: 8-Hydroxy-1-(3-phenylpropyl)-5,6-dihydrobenzo[b]azo-2,4(1H,3H)-dione
[0029]
[0030] Add hydroquinone (55 mg, 0.5 mmol), 1-(3-phenylpropyl)-piperidin-4-one (162.8 mg, 0.75 mmol) and photosensitizer iron phthalocyanine ( II) (11.4 mg, 2 mmol %), a mixed solvent of acetic acid (1 mL) and water (2ml). The reaction mixture was reacted for 36 hours under the irradiation of a 5 W LED white light under an oxygen atmosphere at room temperature. Upon completion, the reaction mixture was washed with NaHCO 3 The aqueous solution was quenched, then ethyl acetate (10 mL) was added to dissolve the reaction system, and the reaction system was washed with water (2×10 mL) and brine (10 mL) successively. The aqueous phase was further extracted with ethyl acetate (10 mL) and washed as before. The combined organic phases were washed with anhydrous Na 2 SO 4 Dried and concentrated. Purified by silica gel column chromatography, 8-hydroxy-1-(3-phenylpropyl)-5,6-dihydrobe...
Embodiment 3
[0032] Example 3: 8-Hydroxy-1-isopropyl-5,6-dihydrobenzo[b]azooctane-2,4(1H,3H)-dione
[0033]
[0034] Add hydroquinone (55 mg, 0.5 mmol) into a 10 mL reaction tube, N - Mixed solvent of isopropyl-4-piperidone (105.8mg, 0.75 mmol), photosensitizer iron(II) phthalocyanine (11.4 mg, 2 mmol %), acetic acid (1 mL) and water (2ml). The reaction mixture was reacted for 36 hours under the irradiation of a 5 W LED white light under an oxygen atmosphere at room temperature. Upon completion, the reaction mixture was washed with NaHCO 3 The aqueous solution was quenched, then ethyl acetate (10 mL) was added to dissolve the reaction system, and the reaction system was washed with water (2×10 mL) and brine (10 mL) successively. The aqueous phase was further extracted with ethyl acetate (10 mL) and washed as before. The combined organic phases were washed with anhydrous Na 2 SO 4 Dried and concentrated. Purified by silica gel column chromatography, 8-hydroxy-1-isopropyl-5,6-dihydr...
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