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Synthesis method of polysubstituted 1,3-dihydronaphtho[2,3-c]furan derivative

A technology of furan derivatives and synthesis methods, which is applied in the field of synthesis of multi-substituted 1,3-dihydronaphtho[2,3-c]furan derivatives, can solve the problem of limited applicability of substrates, harsh reaction conditions, Problems such as poor atom economy, to meet the needs of large-scale applications and development, short response time, and good results

Active Publication Date: 2020-06-19
HAINAN MEDICAL COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw materials used in this method are complex, the reaction conditions are harsh, and two metals and additives are required; and the atom economy of the reaction is poor, and the substrate applicability of the reaction is also limited.

Method used

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  • Synthesis method of polysubstituted 1,3-dihydronaphtho[2,3-c]furan derivative
  • Synthesis method of polysubstituted 1,3-dihydronaphtho[2,3-c]furan derivative
  • Synthesis method of polysubstituted 1,3-dihydronaphtho[2,3-c]furan derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of polysubstituted 1,3-dihydronaphtho[2,3-c]furan compound 1 with the following structural formula:

[0038]

[0039] In the reaction tube, add 2-methyl-4-phenylbut-3-yn-2-ol (0.5mmol), AgSbF 6 (5mol%) and 1,2-dichloroethane (1ml), the mixture was stirred and reacted at 80°C for 1h, the reaction was stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, which was separated and purified by column chromatography to obtain Yellow solid product with a yield of 88%, the structural characterization data are as follows:

[0040] 1 H NMR (400MHz, CDCl 3 )δ7.86(d,J=8.2Hz,1H),7.59(s,1H),7.50~7.40(m,4H),7.30(m,4H),1.65(s,6H),1.35(s,6H ); its hydrogen spectrum is shown in the attached figure 1 .

[0041] 13 C NMR (101MHz, CDCl 3 )δ146.3, 142.5, 137.4, 133.5, 133.4, 133.4, 131.2, 127.9, 127.7, 127.7, 126.5, 125.6, 125.4, 119.0, 84.9, 82.3, 31.4, 30.8; figure 2 .

[0042] HRMS (ESI-TOF) (m / z): C 22 h ...

Embodiment 2

[0044] Preparation of polysubstituted 1,3-dihydronaphtho[2,3-c]furan compound 2 with the following structural formula:

[0045]

[0046] In the reaction tube, add 1-(phenylethynyl)cyclobutanol (0.5mmol), AgSbF 6 (5mol%) and 1,2-dichloroethane (1ml), the mixture was stirred and reacted at 80°C for 1h, the reaction was stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, which was separated and purified by column chromatography to obtain Yellow solid product, the yield is 92%, and the structural characterization data are as follows:

[0047] 1 H NMR (400MHz, CDCl 3 )δ7.89(d,J=10.0Hz,2H),7.50(d,J=4.9Hz,3H),7.44(m,3H),7.33(m,2H),2.71(dd,J=21.0,10.2 Hz, 2H), 2.54(dd, J=15.5, 9.6Hz, 2H), 2.41(t, J=8.3Hz, 4H), 2.13~2.02(m, 2H), 1.61(m, 1H), 0.65(m ,1H); its hydrogen spectrum is shown in the attached image 3 .

[0048] 13 C NMR (101MHz, CDCl 3)δ145.4, 140.8, 137.4, 133.6, 133.5, 133.1, 131.0, 128.0, 127.8, 127.6, 1...

Embodiment 3

[0051] Preparation of polysubstituted 1,3-dihydronaphtho[2,3-c]furan compound 3 with the following structural formula:

[0052]

[0053] In the reaction tube, add 1-(phenylethynyl) cyclopentanol (0.5 mmol), AgSbF 6 (5mol%) and 1,2-dichloroethane (1ml), the mixture was stirred and reacted at 80°C for 1h, the reaction was stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, which was separated and purified by column chromatography to obtain Yellow solid product, the yield is 86%, and the structural characterization data are as follows:

[0054] 1 H NMR (400MHz, CDCl 3 )δ7.82(d,J=8.1Hz,1H),7.57(s,1H),7.46~7.36(m,4H),7.28(m,2H),7.23(m,2H),2.16~2.01(m ,4H), 1.99~1.78(m,8H), 1.69~1.55(m,2H), 1.07(m,2H); Figure 5 .

[0055] 13 C NMR (101MHz, CDCl 3 )δ146.7, 141.7, 137.6, 133.7, 133.4, 133.0, 131.2, 128.0, 127.7, 127.5, 126.3, 125.4, 125.2, 118.3, 94.4, 92.1, 43.4, 42.2, 25.3, 25.2; Image 6 .

[0056] HRMS (ESI-T...

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Abstract

The invention discloses a synthesis method of a polysubstituted 1,3-dihydronaphtho[2,3-c]furan derivative. The synthesis method comprises the following steps: in the presence of a metal salt and an organic solvent, carrying out an intermolecular self-coupling cyclization reaction on a 3-aryl-2-propyn-1-ol compound, and after the reaction is finished, carrying out post-treatment to obtain the polysubstituted 1,3-dihydronaphtho[2,3-c]furan derivative. According to the invention, reaction conditions are mild and simple, only a catalytic amount of the metal salt needs to be added, and other additives and ligands do not need to be added; the reaction process does not need anhydrous and anaerobic conditions, operation is simple and convenient, reaction time is short, reaction yield is high, andthe adaptability of a reaction substrate is good; and meanwhile, only water is produced as a by-product in the preparation method, so the preparation method has higher atom economy. In addition, an amplification experiment of the preparation method disclosed by the invention can be well realized, so the preparation method can meet requirements for large-scale application and development in the fields of biological medicines and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of multi-substituted 1,3-dihydronaphtho[2,3-c]furan derivatives. Background technique [0002] The 1,3-dihydronaphtho[2,3-c]furan skeleton structure is an important structural unit of many active drug molecules and natural products, and has shown excellent pharmacological activities in antiviral, anti-inflammatory and anti-cancer aspects. It has broad application prospects. Therefore, the development of efficient and simple strategies to synthesize such framework compounds has potential application value in real life. [0003] The synthesis of 1,3-dihydronaphtho[2,3-c]furans by transition metal-catalyzed cyclization reactions has been reported for a long time. For example, the Balamurugan research group reported the use of gold as a catalyst to achieve intramolecular electrophilic substitution / cyclization reactions to construct such skeleton compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C07D307/94C07D493/20
CPCC07D307/92C07D307/94C07D493/20
Inventor 陈训徐丹白丽丽孔杜林
Owner HAINAN MEDICAL COLLEGE
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