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Polysubstituted benzo hetero aromatic ring and method for one step synthesizing polysubstituted benzo hetero aromatic ring

A synthesis method and a multi-substituted technology are applied in the field of synthesis of multi-substituted benzoheteroaromatic rings, can solve problems such as cumbersome transformation steps, and achieve the effects of simple synthesis method, good water resistance and air stability, and easy synthesis.

Inactive Publication Date: 2006-07-26
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] From the perspective of traditional methods, the introduction of substituent groups on the benzene ring or naphthalene ring usually requires multi-step conversion, and the conversion steps required to introduce more and different groups will be more cumbersome

Method used

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  • Polysubstituted benzo hetero aromatic ring and method for one step synthesizing polysubstituted benzo hetero aromatic ring
  • Polysubstituted benzo hetero aromatic ring and method for one step synthesizing polysubstituted benzo hetero aromatic ring
  • Polysubstituted benzo hetero aromatic ring and method for one step synthesizing polysubstituted benzo hetero aromatic ring

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Compound 1: Put 2-furyl boronic acid (50.4 mg, 0.45 mmol) and tetrakis-(triphenylphosphine) palladium (17.3 mg, 0.015 mmol) into a dry Schlenk reaction tube, fill with argon, add tetrahydrofuran (2.0 mL). After 10 minutes a stirred solution of the substrate (54.6 mg, 0.3 mmol) in THF (1.0 mL) was injected. The temperature of the reaction mixture was refluxed in an oil bath until the reaction of the raw materials was completed. After cooling to room temperature, the solvent was distilled off and separated by column chromatography (petroleum ether: ethyl acetate) to obtain a colorless liquid. Yield: 67%; 1 H NMR (300MHz, CDCl 3 ): δ7.60(d, J=2.4Hz, 1H), 7.17(s, 1H), 6.76(d, J=2.4Hz, 1H), 5.23(s, 2H), 5.18(s, 2H), 2.37 (s, 3H); 13 C NMR (75MHz, CDCl 3): δ154.9, 145.0, 135.1, 131.6, 127.1, 123.4, 104.9, 101.4, 73.7, 72.5, 15.7; MS (EI, 70eV): m / z (%): 174 (M + , 35), 159(41), 145(100), 131(23), 115(28); IR(CHCl 3 , cm -1 ): 2852(s), 1382(s), 1297(s), 1141(s), 1038(...

Embodiment 2

[0041] Compound 2: put 2-furyl boronic acid (50.4mg, 0.45mmol) and tetrakis-(triphenylphosphine) palladium (17.3mg, 0.015mmol) into the dry Schlenk reaction tube, fill with argon, add tetrahydrofuran (2.0 mL). After 10 minutes a stirred solution of the substrate (77.4 mg, 0.3 mmol) in THF (1.0 mL) was injected. The temperature of the reaction mixture was refluxed in an oil bath until the reaction of the raw materials was completed. After cooling to room temperature, the solvent was distilled off and separated by column chromatography (petroleum ether: ethyl acetate) to obtain a colorless liquid. Yield: 75%; 1 H NMR (300MHz, CDCl 3 ): δ7.58(d, J=2.1Hz, 1H), 7.29-7.13(m, 6H), 6.69(dd, J=1.2, 2.1Hz, 1H), 5.18(s, 2H), 5.04(s, 2H), 4.11(s, 2H); 13 C NMR (75MHz.CDCl 3 ): δ155.2, 145.1, 139.2, 136.4, 132.9, 128.6, 128.4, 127.1, 126.3, 126.2, 105.1102.2, 73.5, 72.3, 36.8; m + , 82), 221(38), 172(100), 159(34), 131(35), 115(47), 78(40), 51(41); IR(CHCl 3 , cm -1 ): 2849(m), 1...

Embodiment 3

[0043] Compound 3: put 2-furyl boronic acid (50.4mg, 0.45mmol) and tetrakis-(triphenylphosphine) palladium (17.3mg, 0.015mmol) into the dry Schlenk reaction tube, fill with argon, add tetrahydrofuran (2.0 mL). After 10 minutes a stirred solution of the substrate (85.8 mg, 0.3 mmol) in THF (1.0 mL) was injected. The temperature of the reaction mixture was refluxed in an oil bath until the reaction of the raw materials was completed. After cooling to room temperature, the solvent was distilled off and separated by column chromatography (petroleum ether: ethyl acetate) to obtain a colorless liquid. Yield: 63%; 1 H NMR (300MHz, CDCl 3 ): δ7.60(d, J=2.1Hz, 1H), 7.57-7.54(m, 2H), 7.50-7.45(m, 2H), 7.40-7.36(m, 1H), 6.91(d, J=2.1 Hz, 1H), 5.26(s, 2H), 5.20(s, 2H), 3.15(h, J=6.9Hz, 1H), 1.40(d, J=6.9Hz, 6H); 13 C NMR (75MHz, CDCl 3 ): δ152.9, 144.7, 134.8, 134.6, 133.4, 131.6, 129.0, 128.5, 127.7, 125.5, 117.7, 106.0, 72.9, 72.6, 31.8, 22.0; MS (EI, 70eV): m / z (%): 278(M + , 1...

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Abstract

The present invention relates to a kind of polysubstituted benzo hetero aromatic ring and its one-step controllable synthesis process. By means of the said process, it is easy to constitute coumarone, benzothiophene, indole, etc. with the same or dislike substitution radicals in different positions. The process is simple, practical and effective in constituting polysubstituted benzo hetero aromatic ring. The product of the present invention is one kind of important medicine intermediate and analog and has important application value for medicine screening in pharmaceutical industry.

Description

technical field [0001] The invention relates to a multi-substituted benzoheteroaromatic ring and an effective method for synthesizing a multi-substituted benzoheteroaromatic ring. By using the method, various identical or different substituent groups on multiple positions can be synthesized through a simple one-step reaction. Naphthalene ring and benzoheteroaryl ring. Background technique [0002] From the perspective of traditional methods, the introduction of substituent groups on the benzene ring or naphthalene ring usually requires multi-step transformation, and the transformation steps required to introduce more and different groups will be more cumbersome. For example, the application of positioning groups (such as the sulfonic acid group can control the reaction at the meta-position, the amino group and the alkoxy group can control the reaction at the ortho-position and the para-position, etc.) needs to introduce and remove the positioning group. So more often, the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77C07D333/50C07D493/04C07D491/048C07D495/04
Inventor 张兆国王峰童晓峰
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI