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Synthetic method of polybrominated benzo[1,3]oxazine derivatives

A synthesis method and technology of bromobenzene, applied in the direction of organic chemistry and the like, can solve the problems of harsh reaction conditions, large pollution of organic solvents, etc., and achieve the effects of simple and mild reaction conditions, cheap raw materials, and easy availability of raw materials

Active Publication Date: 2020-06-30
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the method for synthesizing benzoxazine compounds through o-alkenylaniline compounds has some common characteristics: 1) react in the organic phase; 2) based on the reaction starting reagent, only a single functionalized product
In addition, there are disadvantages such as harsh reaction conditions, the need for various additives, activating reagents, noble metal catalysis, and the use of highly polluting organic solvents.

Method used

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  • Synthetic method of polybrominated benzo[1,3]oxazine derivatives
  • Synthetic method of polybrominated benzo[1,3]oxazine derivatives
  • Synthetic method of polybrominated benzo[1,3]oxazine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of 6-bromo-4-(bromomethyl)-4-methyl-2-phenyl-4H-benzo[d][1,3]oxazine

[0032] Weigh 0.3mmol N-(2-(prop-1-en-2-yl) phenyl) benzamide (compound corresponding to numbering (1), 0.0710g), 1.5mmol N-bromosuccinimide ( The compound corresponding to number (II), 0.2670g) was placed in a 10mL test tube reaction tube, 3mL of water was added as a solvent, the test tube mouth was closed with a rubber stopper, and the reaction was stirred at 80°C for 2 hours; Ester extraction, anhydrous sodium sulfate drying and column chromatography separation (column chromatography separation conditions: the stationary phase is 300-400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) was 1:100), and 0.1067 g of the reaction product was obtained.

[0033] The above-mentioned reaction product is characterized, and the result is:

[0034] 1 H NMR (400MHz, CDCl 3)δ=8.14(d,J=6.3Hz,2H),7.47-7.32(m,3H),7.27(s,2H),7...

Embodiment 2

[0037] Synthesis of 6-bromo-4-(bromomethyl)-4-methyl-2-(p-tolyl)-4H-benzo[d][1,3]oxazine

[0038] Weigh 0.3mmol 4-methyl-N-(2-(prop-1-en-2-yl)phenyl)benzamide (compound corresponding to number (2), 0.0753g), 1.5mmolN-bromobutyl Diimide (the compound corresponding to numbering (II), 0.2670g) was placed in a 10mL test tube reaction tube, and 3 mL of water was added as a solvent, and the test tube mouth was closed with a rubber stopper, and stirred and reacted at 80° C. for 2 hours; after the reaction, the reaction The solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and separated by column chromatography (column chromatography separation conditions: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was ethyl acetate (A) and petroleum ether (B). , mobile phase change program (A:B) is 1:100), to obtain 0.0859g reaction product.

[0039] The above-mentioned reaction product is characterized, and the result is:

[0040] 1...

Embodiment 3

[0043] Synthesis of 6-bromo-4-(bromomethyl)-4-methyl-2-(o-tolyl)-4H-benzo[d][1,3]oxazine

[0044] Weigh 0.3mmol 2-methyl-N-(2-(prop-1-en-2-yl)phenyl)benzamide (compound corresponding to number (3), 0.0753g), 1.5mmolN-bromobutyl Diimide (the compound corresponding to numbering (II), 0.2670g) was placed in a 10mL test tube reaction tube, and 3 mL of water was added as a solvent, and the test tube mouth was closed with a rubber stopper, and stirred and reacted at 80° C. for 2 hours; after the reaction, the reaction The solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and separated by column chromatography (column chromatography separation conditions: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was ethyl acetate (A) and petroleum ether (B). , mobile phase change program (A:B) is 1:100), and 0.0798g of reaction product was obtained.

[0045] The above-mentioned reaction product is characterized, and the result is:

...

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Abstract

The invention relates to a synthesis method for a polybrominated benzene [1.3] oxazine derivative, comprising the following steps of: carrying out reaction of compounds shown in formula (I) and N-bromo-succinimide (NBS) in a solvent at 25-100 DEG C to obtain the polybrominated benzene [1.3] oxazine derivative shown in formula (II) after the reaction is completed. The compounds shown in the formula(I) and the formula (II) are as shown in the description, wherein R is chosen from phenyl, substituted phenyl, C1-C5 alkyl (preferably isopropyl) or thiophene. The synthesis method has the advantagesof being mild in reaction conditions, environment-friendly, simple in operation and capable to obtain polybrominated benzene oxazine compounds which cannot be obtained by conventional methods throughone pot multi-step reaction.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing polybrominated benzo[1,3]oxazine derivatives. Background technique [0002] Benzoxazine compounds widely exist in some natural products, have certain biological activities and drug effects, and have been used as anxiolytic and anticonvulsant drugs, fungicides and progesterone receptor agonists, etc. (J.Med. Chem., 1990,33,464; J.Med.Chem., 1998,41,1060; Bioorg.Med.Chem.Lett., 2002,12,787.), also can participate in reaction as important synthon and intermediate simultaneously (Pharm . Biomed. Anal., 2014, 100, 11; J. Med. Chem., 2002, 45, 4379.). This makes the synthesis of such compounds have received extensive attention in the fields of medicinal chemistry and organic synthetic chemistry. [0003] At present, the reaction of o-alkenylaniline compounds for the synthesis of benzazine heterocyclic compounds has been widely studied, and the reaction of io...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/16C07D413/04
CPCC07D265/16C07D413/04
Inventor 徐小平纪顺俊张旭
Owner SUZHOU UNIV
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