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Benzo-beta-lactam and preparation method thereof

A lactam and benzo technology, applied in the chemical field, can solve the problems of low yield, many side reactions, and many by-products, and achieve the effects of high yield, easy operation, and short reaction cycle

Inactive Publication Date: 2020-11-17
LANZHOU JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method include: 1) benzimide has weak nucleophilicity, and simple halogenated hydrocarbons cannot react with it, requiring special alkylating reagents; 2) there are many side reactions and low yield; 3) Not suitable for N-aryl or N-acylbenzo β-lactam compounds
The disadvantages of this method include: 1) It is only applicable to N-acylbenzo β-lactams, and it is not suitable for N-alkyl and N-aryl benzo β-lactams; 2) By-products generated after the decomposition of the condensing agent More, poor atom economy; 3) The condensing agent is expensive
In addition, pyrolysis or photolysis of isatin, phthalimide, and isatoic anhydride can also prepare benzoβ-lactams, but due to the limitation of raw materials, it is only limited to the synthesis of benzoβ-lactams without substituents on nitrogen atoms. Lactams [Hanna Rostkowska, Leszek Lapinski, Maciej J. Nowak, J. Phys. Chem. A, 2020, 124, 4106-4114]

Method used

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  • Benzo-beta-lactam and preparation method thereof
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  • Benzo-beta-lactam and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation reaction formula of N-hydrobenzo β-lactam is as follows:

[0043]

[0044] Dissolve 27.2mg (0.2mmol) of anthranilamide (1a) in 2.0mL of acetonitrile (analytical grade), and stir in a 10mL reaction kettle at room temperature (20°C-25°C). Then 23uL (0.4mmol, 2equiv) glacial acetic acid was added, and 36uL (0.3mmol, 1.5equiv) tert-butyl nitrite was added two minutes later. Stirring was continued for 0.5 h and the reaction was complete. After the reaction was completed, 10.0 mL of water and 10.0 mL of ethyl acetate were added for extraction, and the organic phase was washed with saturated sodium carbonate solution and saturated brine respectively, then dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product, which was finally washed with Ethyl acetate:petroleum ether=1:2 washing solution was purified by column chromatography to obtain the pure product N-hydrobenzoβ-lactam (2a). Th...

Embodiment 2

[0046] The preparation reaction formula of N-hydrobenzo β-lactam is as follows:

[0047]

[0048]1.39 g (10.0 mmol) of anthranilamide (1a) was dissolved in 20.0 mL of acetonitrile (analytical grade), and stirred in a 100 mL reaction kettle at room temperature (20°C-25°C). Then 1.15mL (20.0mmol, 2equiv) of glacial acetic acid was added, and 1.80mL (15.0mmol, 1.5equiv) of tert-butyl nitrite was added two minutes later. Stirring was continued for 1.5 h and the reaction was complete. After the reaction was completed, 100.0 mL of water and 100.0 mL of ethyl acetate were added for extraction. The organic phase was washed with saturated sodium carbonate solution and saturated brine respectively, then dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product. Ethyl acetate:petroleum ether=1:2 washing solution was purified by column chromatography to obtain the pure product N-hydrobenzoβ-lactam (2a). This comp...

Embodiment 3

[0050] The preparation reaction formula of N-hydrobenzo β-lactam is as follows:

[0051]

[0052] 27.2 mg (0.2 mmol) of anthranilamide (1a) was dissolved in 2.0 mL of distilled water, and stirred in a 10 mL reaction kettle at room temperature (20°C-25°C). Then 23uL (0.4mmol, 2equiv) of glacial acetic acid was added, and 20.7mg (0.3mmol, 1.5equiv) of sodium nitrite was added two minutes later. Stirring was continued for 0.5 h and the reaction was complete. After the reaction, add 10.0mL water and 10.0mL ethyl acetate for extraction, wash the organic phase with saturated sodium carbonate solution and saturated brine respectively, then dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain the crude product. Ethyl acetate:petroleum ether=1:2 washing solution was purified by column chromatography to obtain the pure product benzo β-lactam (2a). The compound is a known compound, and the yield is 98%.

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PUM

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Abstract

The invention provides benzo-beta-lactam and a preparation method thereof. The benzo-beta-lactam is mainly structurally characterized by having a skeleton of benzo-beta-lactam. The benzo-beta-lactam can be synthesized by diazotization by taking simple o-aminobenzamide and derivatives thereof as initial raw materials, the reaction conditions are mild, the yield is relatively high, and the reactionspeed is high; a beta-lactam skeleton generally exists in drug molecules, and the benzo-beta-lactam compound has anti-cancer, antibacterial and antifungal activity and the like.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a benzo β-lactam and a preparation method thereof. Background technique [0002] Benzo β-lactam compounds have anticancer, antibacterial, antifungal and other pharmacological activities, and have great application potential in the field of medicine. However, this kind of compound has a four-membered ring lactam skeleton with relatively high tension, which is easy to decompose, so its synthesis is relatively difficult. There are two main synthesis methods of benzoβ-lactam compounds reported in the literature at present. The first type is to use benzimide as a raw material, which is alkylated, and then rearranged into a benzo-β-lactam under the action of a base [R.A.Olofson, Robert K.Vander Meer, Stamoulis Stournas, J. Am. Chem. Soc., 1971, 93, 1543-1544; R.A. Olofson, Robert K. Vander Meer, Dennis H. Hoskin, Marguerite Y. Bernheim, Stamoulis Stournas, David S. Morrison, J. O...

Claims

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Application Information

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IPC IPC(8): C07D205/12A61P35/00A61P31/04A61P31/10
CPCA61P31/04A61P31/10A61P35/00C07D205/12
Inventor 徐长明黄金程
Owner LANZHOU JIAOTONG UNIV
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