Synthesis method of N-substituted hydantoin compound

A technology of hydantoin and synthesis method, which is applied in the field of synthesis of N-substituted hydantoin compounds, can solve the problems of unfriendly environment, and achieve the effect of lowering blood sugar and inhibiting uremic toxins

Active Publication Date: 2020-11-03
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, it is inevitable to use catalysts and solvents in the synthesis of N-substituted hydantoin compounds, and it is extremely environmentally unfriendly to toxic additives

Method used

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  • Synthesis method of N-substituted hydantoin compound
  • Synthesis method of N-substituted hydantoin compound
  • Synthesis method of N-substituted hydantoin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Add 0.6 mmol benzoyl azide compound, 0.5 mmol phenylglycine ethyl ester, and 0.75 mmol potassium carbonate to a 25 ml screw-top test tube successively, stir and react at 100°C for 8 hours, and cool to room temperature after the reaction , the crude product can be obtained, and the crude product is purified by column chromatography to obtain the product 3aa with a yield of 92% and a purity of 99%.

[0065] The synthetic route is:

[0066]

[0067] The resulting product 3aa is a yellow solid, and its hydrogen spectrum and carbon spectrum are as follows figure 1 and figure 2 As shown, the structural characterization data are as follows:

[0068] 1 H NMR (500MHz, CDCl 3 )δ7.63(d, J=7.9Hz, 2H), 7.52-7.49(m, 2H), 7.46-7.40(m, 5H), 7.20(t, J=7.4Hz, 1H), 7.20(t, J= 7.4Hz, 1H), 4.48(s, 2H); 13 C NMR (126MHz, CDCl 3 ) δ 187.0, 161.9, 158.7, 156.3, 146.5 132.2, 131.8, 130.7, 129.4, 125.2, 120.8, 49.8.

Embodiment 2

[0070] Add 0.6 mmol of 4-tert-butylbenzoyl azide, 0.5 mmol of ethyl phenylglycine, and 0.75 mmol of potassium carbonate to a 25 ml screw-top test tube in turn, stir and react at 100°C for 8 hours, and the reaction ends After cooling to room temperature, the crude product was obtained, which was purified by column chromatography to obtain the product 3ab with a yield of 75% and a purity of 99%.

[0071] The synthetic route is:

[0072]

[0073] The resulting product 3ab is a light yellow solid, and its hydrogen spectrum and carbon spectrum are as follows image 3 and Figure 4 As shown, the structural characterization data are as follows:

[0074] 1 H NMR (500MHz, CDCl 3 )δ7.62(d, J=7.9Hz, 2H), 7.52(d, J=8.6Hz, 2H), 7.42(t, J=8.0Hz, 2H), 7.37(d, J=8.6Hz, 2H) ,7.19(t,J=7.4Hz,1H),4.45(s,2H),1.35(s,9H); 13 CNMR (126MHz, CDCl 3 ) δ 167.6, 153.4, 151.7, 137.5, 129.4, 128.5, 126.3, 125.9, 124.7, 118.6, 49.8, 34.8, 31.3.

Embodiment 3

[0076] Add 0.6 mmol of 4-methoxybenzoyl azide, 0.5 mmol of ethyl phenylglycine, and 0.75 mmol of potassium carbonate to a 25 ml screw-top test tube in turn, stir and react at 100°C for 8 hours, and the reaction ends After cooling to room temperature, the crude product can be obtained, and the crude product is purified by column chromatography to obtain the product 3ac with a yield of 80% and a purity of 99%.

[0077] The synthetic route is:

[0078]

[0079] The resulting product 3ac is a light yellow solid, and its hydrogen spectrum and carbon spectrum are as follows Figure 5 and Figure 6 As shown, the structural characterization data are as follows:

[0080] 1 H NMR (500MHz, CDCl 3 )δ7.66-7.58(m, 2H), 7.41(t, J=8.0Hz, 2H), 7.34(d, J=9.6Hz, 2H), 7.19(t, J=7.4Hz, 1H), 7.00( d, J=2.7Hz, 2H), 4.43(s, 2H), 3.98(s, 3H); 13 CNMR (126MHz, CDCl 3 ) δ 167.7, 159.5, 153.5, 137.5, 129.4, 127.7, 124.8, 123.9, 118.6, 114.6, 55.6, 49.8.

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Abstract

The invention discloses a synthesis method of an N-substituted hydantoin compound, which comprises the following steps: by using an acyl azide compound as shown in formula I and a glycine ethyl estercompound as shown in formula II as raw materials, carrying out heating reaction in the presence of an additive to obtain the N-substituted hydantoin compound as shown in formula III, wherein the reaction equation is shown as the specification; in the equation, R1 and R2 are independently selected from alkyl, substituted alkyl, aryl, substituted aryl or aromatic heteroradical, the R2 is selected from alkyl or aryl, and R3 is selected from a hydrogen atom and a hydrocarbyl group. The synthesis method can efficiently synthesize the functionalized N-substituted hydantoin compound, has the advantages of few synthesis steps, mild conditions, safe operation, nontoxic, cheap and easily available raw materials, good compatibility with functional groups and high atom economy, can obtain the N-substituted hydantoin compound with a novel structure and a nitrogen-containing heterocyclic skeleton, and has the yield of 92% and the purity of 99% , and the industrial synthesis is easy.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of N-substituted hydantoin compounds. Background technique [0002] Hydantoin compounds belong to a class of compounds of imidazole derivatives. Since the substituting groups of hydantoin are different and the substitution sites are many, and the substituting groups have biological activity, the interaction between groups role, leading to hydantoin compounds have a variety of pharmacological effects. The pharmacological effects of hydantoin compounds are mainly manifested in antibacterial, anti-inflammatory, lowering blood sugar, sodium ion channel blockers, and inhibiting the production of uremic toxins. In the field of medicine, hydantoin is one of the important intermediates for the synthesis of various amino acids, and some of its derivatives also have extremely wide uses, such as 5,5-diphenylhydantoin and other derivatives can be use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/74C07D409/04C07D405/04
CPCC07D233/74C07D409/04C07D405/04
Inventor 朱忠智梁京文林晗泽郭大俊邝妙慈陈修文朱伟东
Owner WUYI UNIV
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