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NOBIN biaryl compound and synthesis method thereof

A synthesis method and compound technology, which are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of few reports on the construction methods of NOBIN biaryl compounds, and achieve excellent regioselectivity and good functional groups. The effect of compatibility, good yield

Active Publication Date: 2021-06-08
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] At present, there are many documents on the synthesis methods of BINOL and BINAP biaryl compounds, but there are relatively few reports on the construction methods of NOBIN biaryl compounds.

Method used

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  • NOBIN biaryl compound and synthesis method thereof
  • NOBIN biaryl compound and synthesis method thereof
  • NOBIN biaryl compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1, the synthesis of N-(1-(2-hydroxyphenyl) naphthalene-2-yl) benzamide

[0073]

[0074] In a 25mL reaction tube, add N-hydroxy-N-(naphthalene-2-yl)benzamide (0.2mmol, 53mg), phenylboronic acid (0.3mmol, 37mg), Cu(OTf) 2 (0.3mmol, 72mg) and Pyridine (0.3 mmol, 24 μL) was added to a solution of molecular sieves (100 mg) in DCM (2 mL), the mixture was stirred at room temperature, and the reaction progress was tracked by TLC. After the reaction was completed, the reaction mixture was filtered through diatomaceous earth, and the filtrate was washed with 3M Washed with HCl, extracted with dichloromethane, the organic phase was dried and concentrated, and the crude product was subjected to column chromatography (eluent was dichloromethane:ethyl acetate=80:1) to obtain white powdery pure product N-(1-(2 -Hydroxyphenyl)naphthalen-2-yl)benzamide, the yield was 88%.

[0075] 1 H NMR (500MHz, DMSO-d 6 ): δ9.82(s,1H),9.22(s,1H),8.10-7.93(m,3H),7.71(t,J=10.7Hz,2H)...

Embodiment 2

[0077] Embodiment 2, the synthesis of N-(1-(2-hydroxyl-5-methylbenzene) naphthalene-2-yl) benzamide

[0078]

[0079] In a 25mL reaction tube, add N-hydroxy-N-(naphthalene-2-yl)benzamide (0.2mmol, 53mg), p-tolylboronic acid (0.3mmol, 41mg), Cu(OTf) 2 (0.3mmol, 72mg) and Pyridine (0.3 mmol, 24 μL) was added to a solution of molecular sieves (100 mg) in DCM (2 mL), the mixture was stirred at room temperature, and the reaction progress was tracked by TLC. After the reaction was completed, the reaction mixture was filtered through diatomaceous earth, and the filtrate was washed with 3M Washed with HCl, extracted with dichloromethane, the organic phase was dried and concentrated, and the crude product was subjected to column chromatography (eluent was dichloromethane:ethyl acetate=80:1) to obtain white powdery pure product N-(1-(2 -Hydroxy-5-methylphenyl)naphthalen-2-yl)benzamide, yield 89%.

[0080] 1 H NMR (500MHz, DMSO-d 6 ): δ9.61(s,1H),9.13(s,1H),8.07(d,J=8.8Hz,1H),8.0...

Embodiment 3

[0082] Embodiment 3, the synthesis of N-(1-(2-hydroxyl-5-methoxybenzene) naphthalene-2-yl) benzamide

[0083]

[0084] In a 25mL reaction tube, add N-hydroxy-N-(naphthalene-2-yl)benzamide (0.2mmol, 53mg), p-methoxyphenylboronic acid (0.3mmol, 46mg), Cu(OTf) 2 (0.3mmol, 72mg) and Pyridine (0.3 mmol, 24 μL) was added to a solution of molecular sieves (100 mg) in DCM (2 mL), the mixture was stirred at room temperature, and the reaction progress was tracked by TLC. After the reaction was completed, the reaction mixture was filtered through diatomaceous earth, and the filtrate was washed with 3M Washed with HCl, extracted with dichloromethane, the organic phase was dried and concentrated, and the crude product was subjected to column chromatography (eluent was dichloromethane:ethyl acetate=80:1) to obtain white powdery pure product N-(1-(2 -Hydroxy-5-methoxyphenyl)naphthalen-2-yl)benzamide, yield 66%.

[0085] 1 H NMR (500MHz, DMSO-d 6 ):δ9.33(s,1H),9.25(s,1H),8.05-7.92(m,3...

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Abstract

The invention relates to a NOBIN biaryl compound and a synthesis method thereof. The compound has a structure as shown in a formula (III). The method comprises the following steps: mixing a compound (I), a compound (II), a copper salt, alkali and a molecular sieve, adding a solvent, reacting at room temperature in an air atmosphere for 12-24 hours, and purifying after the reaction is completed, thereby obtaining the target compound (III). According to the present invention, the Chan-Lam oxyarylation reaction of aryl hydroxylamine and aryl boric acid is utilized to produce the transient N,O-diaryl intermediate, and the intermediate rapidly carries out [3,3]-rearrangement and re-aromatization so as to obtain a series of NOBIN biaryl compounds. The compound has good functional group compatibility, and various highly functionalized biaryl products are prepared with good yield and excellent regioselectivity.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to NOBIN biaryl compounds and a synthesis method thereof. Background technique [0002] Biaryl structures widely exist in biologically active natural products, drugs, agrochemicals, and organic functional materials, such as: natural product TMC-95A with anti-cancer effects, antibiotic Biphenomycin B, anti-HIV drug Gossypol, antihypertensive Drug Diovan, axial chiral ligands NOBIN, BINOL, BINAP, new proton conducting polymer Polybiaryl tetra(OH), etc., the structural formula is as follows: [0003] [0004] Therefore, in recent years, more and more research work has been done on the synthesis methods of biaryl compounds, and scientists have made great efforts to study the construction of such structures from a variety of starting materials. [0005] The more traditional way is through the transition metal catalyzed cross-coupling reaction of aryl ha...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/75
CPCC07C231/12C07C233/75
Inventor 王丽英王敏高洪银
Owner SHANDONG UNIV
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