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Spiro[chromane-oxindole] derivatives, synthesis method and application thereof

A technology of indole derivatives and benzopyran spirooxindole derivatives, applied in the field of benzopyranspirooxindole derivatives and their chemical synthesis, can solve the unfavorable industrialization of benzopyranspirooxindole derivatives Synthesis, harsh reaction conditions, long time-consuming and other problems, to achieve the effect of low cost, few reaction steps, and short route

Inactive Publication Date: 2018-04-24
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes methods for making certain types of molecules that can be useful in medicine or other fields like chemistry. These molecular structures are made through specific reactions between different starting material components called reactants. By doing this process at once, these new molecule products will become more efficient than previous ones due to their shorter routes, reliability, quick response time, lower costs, reduced wastage, higher efficiency, etc., resulting from multiple stages involved during each stage.

Problems solved by technology

This patented technical problem addressed by this patent relates to finding ways to efficiently produce certain types of compounds that contain one type of molecule called pyrrolespironolene (BZP).

Method used

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  • Spiro[chromane-oxindole] derivatives, synthesis method and application thereof
  • Spiro[chromane-oxindole] derivatives, synthesis method and application thereof
  • Spiro[chromane-oxindole] derivatives, synthesis method and application thereof

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Effect test

Embodiment 1

[0075]

[0076] 2-(3-(Dibenzylamino)phenol base)-1-acetophenone (0.30mmol), rhodium acetate (0.003mmol), The mixture of molecular sieves (300 mg) was dissolved in 1.5 mL of DCE (1,2-dichloroethane) solvent to prepare a mixed solution A, which was stirred at 25° C. for 10 minutes. Then 1-benzyl-3-diazoindol-2-one (0.33 mmol) was dissolved in 1.0 mL DCE (1,2-dichloroethane) solvent to prepare solution B. Solution B was added to mixed solution A with a syringe pump within 1 hour at 25°C. The reaction mixture was purified by flash column chromatography to obtain a pure product whose structure is shown in formula (a) as (3S,3'S)-1'-benzyl-7-(dibenzylamino)-3-hydroxyl-3- Phenylspiro[chroman-4,3'-indole]-2'-one. Yield 90%, dr value equal to 95:5. of the product 1 H NMR schematic as figure 2 As shown, its 13 C NMR schematic as image 3 shown.

[0077] 1 H NMR (400MHz, CDCl 3 )δ7.35–7.28(m,5H),7.28–7.20(m,6H),7.21–6.99(m,10H),6.63(d,J=7.2Hz,2H),6.47–6.38(m,3H) ,6.23(d,J...

Embodiment 2

[0079]

[0080] 2-(3-(Dibenzylamino)phenol base)-1-(4-methylphenyl)ethanone (0.30mmol), rhodium acetate (0.003mmol), The mixture of molecular sieves (300 mg) was dissolved in 1.5 mL of DCE (1,2-dichloroethane) solvent to prepare a mixed solution A, which was stirred at 25° C. for 10 minutes. Then 1-benzyl-3-diazoindol-2-one (0.33 mmol) was dissolved in 1.0 mL DCE (1,2-dichloroethane) solvent to prepare solution B. Solution B was added to mixed solution A with a syringe pump within 1 hour at 25°C. The reaction mixture was purified by flash column chromatography to obtain a pure product whose structure is shown in formula (b) as (3S,3'S)-1'-benzyl-7-(dibenzylamino)-3-hydroxyl-3- (4-methylphenyl)spiro[chroman-4,3'-indole]-2'-one. The yield was 82%, and the dr value was greater than 95:5. of the product 1 H NMR schematic as Figure 4 As shown, its 13 C NMR schematic as Figure 5 shown.

[0081] 1 H NMR (400MHz, CDCl 3 )δ7.36–6.97(m,16H),6.92–6.78(m,4H),6.65(d,J=7.3Hz...

Embodiment 3

[0083]

[0084] 2-(3-(Dibenzylamino)phenol base)-1-(4-methoxyphenyl)ethanone (0.30mmol), rhodium acetate (0.003mmol), The mixture of molecular sieves (300 mg) was dissolved in 1.5 mL of DCE (1,2-dichloroethane) solvent to prepare a mixed solution A, which was stirred at 25° C. for 10 minutes. Then 1-benzyl-3-diazoindol-2-one (0.33 mmol) was dissolved in 1.0 mL DCE (1,2-dichloroethane) solvent to prepare solution B. Solution B was added to mixed solution A with a syringe pump within 1 hour at 25°C. The reaction mixture was purified by flash column chromatography to obtain a pure product whose structure is shown in formula (c) as (3S,3'S)-1'-benzyl-7-(dibenzylamino)-3-hydroxyl-3- (4-methoxyphenyl)spiro[chroman-4,3'-indole]-2'-one. The yield was 93%, and the dr value was greater than 95:5. of the product 1 H NMR schematic as Image 6 As shown, its 13 C NMR schematic as Figure 7 shown.

[0085] 1 H NMR (400MHz, CDCl 3 )δ7.39–7.00(m,16H),6.92(d,J=8.8Hz,2H),6.66–6.50(m,...

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Abstract

The invention discloses spiro[chromane-oxindole] derivatives and a synthesis method thereof. According to the method, 3-diazooxindole and a 2-phenoxy-substituted ketone are used as raw materials, 4A molecular sieve is taken used as a water-absorbing agent, rhodium acetate is used as a catalyst, and in an organic solvent, a one-step reaction is carried out to obtain the spiro[chromane-oxindole] derivative. The synthesis method of the present invention has the advantages of high atom economy, high selectivity and high yield, the reaction conditions are mild and the operation is simple and safe.The spiro[chromane-oxindole] derivatives having two quaternary carbon centers are an important chemical and pharmaceutical intermediate, are widely used in the field of pharmaceutical and chemical engineering, and have great application prospects.

Description

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Claims

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Application Information

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Owner EAST CHINA NORMAL UNIV
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