Synthesis method of cyclobutanol nitro-substituted naphthol compound

A synthesis method and compound technology, applied in the preparation of nitro compounds, organic chemistry, etc., can solve the problems of a large number of by-products, low product yield, expensive reagents, etc., and achieve simple operation, high atom economy, and wide application range. Effect

Inactive Publication Date: 2019-02-22

HENAN NORMAL UNIV

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AI-Extracted Technical Summary

Problems solved by technology

Although this method is relatively reliable, there are still problems such as expensive reagents and low product yields.

On the other hand, naphthol compounds are mainly realized by methods such as the oxida...

Abstract

The invention discloses a synthesis method of a cyclobutanol nitro-substituted naphthol compound and belongs to the technical field of organic synthesis. The synthesis method of the cyclobutanol nitro-substituted naphthol compound is characterized by comprising the following steps of: dissolving orthoalkynyl substituted phenyl allenyl ketone compound and tert-butyl nitrite in a solvent, and heating in an air atmosphere for a temperature rise reaction to form the cyclobutanol nitro-substituted naphthol compound. The method has the advantages of easiness and simplicity in operation, mild conditions, wide substrate application scope and the like and is suitable for industrial production.

Application Domain

Nitro compound preparation

Technology Topic

Air atmosphereSolvent +5

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Examples

Experimental program(18)

Example Embodiment

[0013] Example 1

[0014]

[0015] 1a (0.5mmol, 122mg), 2 (1.5mmol, 178μL) and acetonitrile (3mL) were sequentially added into a reaction tube, and the reaction was stirred at 50°C for 3h under an air atmosphere. Then the solvent was spin-dried and separated by silica gel column (petroleum ether/ethyl acetate=10/1) to obtain orange solid product 3a (77 mg, 50%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ:3.03(m,1H),3.80(d,J=14.8Hz,1H),3.86(d,J=14.4Hz,1H),7.28-7.34(m,3H),7.42-7.45(m,2H ),7.54-7.58(m,1H),7.61-7.68(m,2H),8.54(d,J=8.4Hz,1H),12.13(s,1H). 13 C NMR (100MHz, CDCl 3 )δ: 51.5, 81.1, 122.9, 125.2, 125.3, 125.9, 126.4, 126.7, 127.8, 128.6, 132.0, 132.2, 134.0, 136.2, 142.3, 156.9. HRMS calcd for C 18 h 13 NO 4 :306.0772[M-H] - ,found: 306.0775.

Example Embodiment

[0016] Example 2

[0017] 1a (0.5mmol, 122mg), 2 (1.5mmol, 178μL) and toluene (3mL) were sequentially added into the reaction tube, and the reaction was stirred at 50°C for 3h under air atmosphere. Then the solvent was spin-dried and separated by silica gel column (petroleum ether/ethyl acetate=10/1) to obtain the orange solid product 3a (49 mg, 32%).

Example Embodiment

[0018] Example 3

[0019] 1a (0.5mmol, 122mg), 2 (1.5mmol, 178μL) and 1,4-dioxane (3mL) were sequentially added into the reaction tube, and the reaction was stirred at 50°C for 3h under air atmosphere. Then the solvent was spin-dried and separated by silica gel column (petroleum ether/ethyl acetate=10/1) to obtain the orange solid product 3a (62 mg, 40%).

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