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New simple method for synthesizing 4H-benzopyran ring heterocyclic compound

A technology for heterocyclic compounds and benzopyran rings, applied in the field of simple synthesis of 4H-benzopyran ring heterocyclic compounds

Inactive Publication Date: 2013-04-17
王飞军 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To the best of our knowledge, a one-step synthesis method to construct the 4H-benzopyran ring nucleus has not been reported

Method used

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  • New simple method for synthesizing 4H-benzopyran ring heterocyclic compound
  • New simple method for synthesizing 4H-benzopyran ring heterocyclic compound
  • New simple method for synthesizing 4H-benzopyran ring heterocyclic compound

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Experimental program
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Effect test

Embodiment 1

[0018] In the presence of 5 mmol of trimethylsilyl chloride, 1 mmol of salicylaldehyde and 1 mmol of ethyl acetoacetate were reacted at room temperature in 2 milliliters of N, N-dimethylformamide, reacted for 12 hours, and reduced Press spin dry solvent, then column chromatography obtains 2-methyl-4H-benzopyran-3-formic acid ethyl ester Ia (in the formula I, R 1 = H, R 2 = Me,R 3 =CO 2 Et), the yield is 85%.

[0019] 1 H NMR (400MHz, CDCl 3 , TMS) δ1.33(t, J=7.2Hz, 3H), 2.38(s, 3H), 3.60(s, 2H), 4.23(dd, J=7.6, 14.4Hz, 2H), 6.90(dd, J =1.2, 8.4Hz, 1H), 7.02(dt, J=1.2, 7.2Hz, 1H), 7.09-7.16(m, 2H); 13 C NMR (100MHz, CDCl 3 , TMS) δ14.4, 19.2, 24.8, 60.1, 100.9, 116.0, 120.5, 124.0, 127.5, 128.7, 150.1, 160.6, 167.6.

Embodiment 2

[0020] Embodiment 2, its specific synthetic steps refer to embodiment 1.

[0021] 6-bromo-2-methyl-4H-benzopyran-3-carboxylic acid ethyl ester Ib (in formula I, R 1 =6-Br, R 2 = Me,R 3 =CO 2 Et), the yield is 76%.

[0022] 1 H NMR (400MHz, CDCl 3 , TMS) δ1.32(t, J=7.2Hz, 3H), 2.37(s, 3H), 3.57(s, 2H), 4.22(dd, J=6.8, 14.0Hz, 2H), 6.78(d, J =9.2Hz, 1H), 7.23-7.24(m, 2H); 13 C NMR (100MHz, CDCl 3 , TMS) δ14.3, 19.1, 24.6, 60.3, 100.7, 116.2, 117.7, 122.7, 130.4, 131.4, 149.3, 160.3, 167.3.

Embodiment 3

[0023] Embodiment 3, its specific synthetic steps refer to embodiment 1.

[0024] 6-iodo-2-methyl-4H-benzopyran-3-carboxylic acid ethyl ester Ic (in formula I, R 1 =6-I, R 2 = Me,R 3 =CO 2 Et), the yield is 76%.

[0025] yellow liquid; 1 H NMR (400MHz, CDCl 3 , TMS) δ1.32(t, J=7.2Hz, 3H), 2.36(s, 3H), 3.56(s, 2H), 4.23(dd, J=7.2, 14.4Hz, 2H), 6.66(d, J =9.2Hz, 1H), 7.42(s, 2H); 13 C NMR (100MHz, CDCl 3 , TMS) δ14.3, 19.2, 24.4, 60.3, 68.7, 100.9, 118.2, 123.3, 136.4, 137.4, 150.1, 160.3, 167.3.

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Abstract

The invention relates to a new simple method for synthesizing a 4H-benzopyran ring heterocyclic compound. The 4H-benzopyran ring heterocyclic compound is prepared by the following steps of: taking salicylic aldehyde or a salicylic aldehyde derivative as a raw material; by utilizing the nucleophilicity of a phenolic hydroxyl group and the electrophilicity of an aldehyde group in the raw material, performing intermolecular cyclization reaction with a beta-dicarbonyl type compound or a carbonyl type compound with an electron withdrawing group in the beta-position in the presence of Lewis acid; and further constructing the heterocyclic compound with a 4H-benzopyran ring mother nucleus through one step. The method has the advantages of simple reaction, high yield, capability of realizing fast synthesis of a large number of various substituted 4H-benzopyran ring heterocyclic compound libraries, and capability of accelerating the discovery of lead compounds of medicaments. In the formula 1, R1, R2, R3, R4, R5 and R6 are respectively and independently selected from one of hydrogen, C1-C6 alkyl, C5-C10 aromatic ring or C5-10 aromatic ring-substituted C1-C6 alkyl, and at least two are different.

Description

technical field [0001] The invention relates to a new method for conveniently synthesizing 4H-benzopyran ring heterocyclic compounds. Background technique [0002] The derivatives of the 4H-benzopyran ring core have rich biological activities, and have a variety of physiological and pharmacological activities, such as anti-dysplasia, can reduce brain and peripheral vascular resistance, lower blood pressure, improve cerebral circulation and coronary circulation , promote the collateral circulation of ischemic myocardium, treat allergic tracheitis, antibacterial, anticancer, lower blood sugar and treat diabetes, etc. Over the years, people have done a lot of research work in this field. The synthesis of benzopyran derivatives and their pharmacological research are very active. People have synthesized many high-efficiency and low-toxic medicinal compounds through various methods. . [0003] However, the traditional synthesis method of benzopyran ring nucleus is mainly obtaine...

Claims

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Application Information

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IPC IPC(8): C07D311/58C07D311/82
Inventor 王飞军屈明亮陈锋李升可施敏
Owner 王飞军
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