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Preparation method of dibenzo [c, e] aza-5, 7 (6H)-dione compound

A compound, diphenyl technology, applied in pharmaceutical and chemical intermediates and related chemical fields, can solve the problems of low cumulative yield, cumbersome steps, complicated operation, etc., and achieve the effect of high yield, simple operation and broad market prospect

Active Publication Date: 2017-05-24
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method has cumbersome steps, harsh conditions, complicated operation, and low cumulative yield, which is inconsistent with the concept of "atom economy" pursued by people.

Method used

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  • Preparation method of dibenzo [c, e] aza-5, 7 (6H)-dione compound
  • Preparation method of dibenzo [c, e] aza-5, 7 (6H)-dione compound
  • Preparation method of dibenzo [c, e] aza-5, 7 (6H)-dione compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 5H-dibenzo[c,e]azepine-5,7(6H)-dione (3a)

[0033]

[0034] Benzamide (121.1mg, 1mmol), tetrakis(triphenylphosphine) palladium (57.8mg 0.05mmol), potassium hypochlorite (181mg, 2mmol) were successively added to the Schlenk reaction flask, vacuum and nitrogen were replaced 3 times, and then In a nitrogen atmosphere, add 2 mL of trifluoroacetic acid, react at 120°C for 24 hours, after the reaction, remove the solvent under reduced pressure, and separate by column chromatography (eluent is petroleum ether: ethyl acetate = 5:1, V:V), 200.7 mg of a white solid product was obtained with a yield of 90%. Mp 184–186°C. 1 H NMR (400MHz, DMSO-d6) δ: 11.71(s, 1H), 7.93(dd, J=7.8, 1.2Hz, 2H), 7.83(d, J=7.8Hz, 2H), 7.80–7.74(m, 2H),7.65–7.58(m,2H); 13 C NMR (100MHz, DMSO-d6) δ: 168.6, 135.4, 133.4, 133.3, 131.0, 130.5, 129.4; HRMS-APCI (m / z): [M-H] - Calculated for C 14 h 8 NO 2 ,222.0561; found, 222.0570.

Embodiment 2

[0035] Example 2: Synthesis of 10-dimethyl-5H-dibenzo[c,e]azepine-5,7(6H)-dione (3b)

[0036]

[0037] Add p-toluamide (135.1mg, 1mmol), palladium acetate (33.7mg, 0.15mmol), sodium hypochlorite (223.2mg, 3mmol) into the Schlenk reaction flask in turn, vacuum and nitrogen replacement for 3 times, in a nitrogen atmosphere 2 mL of trifluoroacetic acid was added to the mixture, and reacted at 90°C for 24 hours. After the reaction, the solvent was removed under reduced pressure and separated by column chromatography (eluent: petroleum ether: ethyl acetate = 5:1, V:V) to obtain light Yellow solid product 225.9 mg, yield 90%. Mp 222–224°C. 1 H NMR (400MHz, DMSO-d6) δ: 11.51(s, 1H), 7.82(d, J=8.0Hz, 2H), 7.65(s, 2H), 7.40(dd, J=8.0, 0.8Hz, 2H) ,2.45(s,6H); 13 C NMR (100MHz, DMSO-d6): 168.4, 143.6, 135.5, 131.2, 130.8, 130.6, 130.0, 21.5; IR (KBr) (cm -1 ):3453.7, 1697.2, 1658.7, 1602.3, 1353.1, 1297.4, 1269.2, 1152.7, 657.0; HRMS-APCI (m / z): [M-H] - Calculated for C 16 h 12...

Embodiment 3

[0038] Example 3: Synthesis of 9,10-tetramethyl-5H-dibenzo[c,e]azepine-5,7(6H)-dione (3c)

[0039]

[0040]3,4-Dimethylbenzamide (149.1mg, 1mmol), palladium trifluoroacetate (33.2mg, 0.1mmol), and ammonium persulfate (228.2mg, 1mmol) were successively added to the Schlenk reaction flask, vacuum, nitrogen After 3 replacements, add 2 mL of trifluoroacetic acid in a nitrogen atmosphere and react at 130°C for 24 hours. After the reaction, remove the solvent under reduced pressure and separate by column chromatography (eluent: petroleum ether: ethyl acetate = 5:1 , V:V) to obtain 178.6 mg of the main product as a white solid, with a yield of 64%. Mp 233–235°C. 1 H NMR (400MHz, DMSO-d6) δ: 11.44(s,1H), 7.70(s,2H), 7.62(s,2H), 2.37(s,6H), 2.32(s,6H); 13 CNMR (100MHz, DMSO-d6): 167.9, 142.0, 137.1, 132.6, 131.3, 130.5, 129.9, 19.4, 18.8; IR (KBr) (cm -1 ):3182.2, 3070.6, 1655.4, 1606.5, 1287.5 427.4; HRMS-APCI (m / z): [M-H] - Calculated for C 18 h 16 NO 2 , 278.1187; found, 2...

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Abstract

The invention belongs to the field of medical and chemical intermediates and related chemical technology, and relates to a preparation method of a dibenzo [c, e] aza-5, 7 (6H)-dione compound. The dibenzo [c, e] aza-5, 7 (6H)-dioneis an important bioactive molecule, has a skeleton structure frequently appearing in a pharmaceutical molecule, has better effects on reducing blood fat, treating obesity, resisting epinephrine and the like, can be significantly applied in the fields such as organic synthesis and pharmaceutical chemistry, and has a wide market prospect. According to the preparation method of the dibenzo [c, e] aza-5, 7 (6H)-dione compound provided by the invention, benzamide is adopted as a raw material, and a series of dibenzo [c, e] aza-5, 7 (6H)-dikone and a derivative thereof are synthesized under the action of a palladium catalyst. The method has the advantages of short synthetic route, simplicity in operation, higher yield and the like. The preparation method of the dibenzo [c, e] aza-5, 7 (6H)-dione compound provided by the invention has a larger use value and social and economic benefits.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a preparation method of a dibenzo[c,e]azepine-5,7(6H)-dione compound. Background technique [0002] Dibenzo[c,e]azepine-5,7(6H)-dione and its derivatives are an important class of molecules with biological activity. Obesity, anti-adrenaline, etc. have good effects, and have important applications in the fields of organic synthesis and medicinal chemistry. [0003] Regarding the synthesis of dibenzo[c,e]azepine-5,7(6H)-dione compounds, the following methods are usually adopted: [0004] [0005] Using anthranilic acid as raw material, dibenzo[c,e]azepine-5,7(6H)-dione was finally synthesized in five steps (JKAU:Med.Sci.2007,14,3–17.) . However, the method has cumbersome steps, harsh conditions, complicated operation, and low cumulative yield, which is inconsistent with the concept of "atom economy" pursued by people. ...

Claims

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Application Information

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IPC IPC(8): C07D223/18C07D223/14
CPCC07D223/14C07D223/18
Inventor 包明于晓强康贝德
Owner DALIAN UNIV OF TECH
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