Preparation method of polysubstituted thiapyran diindyl derivative

A technology of indole derivatives and multi-substitution is applied in the field of preparation of multi-substituted thiopyranoindole derivatives, which can solve the problems of difficulty in synthesizing multi-substituted thiopyranoindole derivatives, expensive catalytic metals, and many synthesis steps. , to achieve the effect of easy purification of the product, simple synthesis method and high yield

Inactive Publication Date: 2016-06-15
QINGDAO UNIV OF SCI & TECH
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  • Claims
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Problems solved by technology

[0009] Utilize above-mentioned method to prepare thiopyranoindole derivatives in laboratory, have obvious shortcoming: 1) synthetic steps are many, and catalytic metal is expensive
2) The reaction is carried out under strong acid or strong alkaline conditions, which has great environmental pollution; 3) It is difficult to synthesize polysubstituted thiopyranoindole derivatives, especially the highly selective synthesis of benzene ring polysubstituted thiopyranoindole derivatives thing

Method used

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  • Preparation method of polysubstituted thiapyran diindyl derivative
  • Preparation method of polysubstituted thiapyran diindyl derivative
  • Preparation method of polysubstituted thiapyran diindyl derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: 11-phenylbenzothiopyranoindole (R in structural formula I 9 = phenyl)

[0035] Add o-alkynyl isothiocyanate (0.5mmol, 117mg), diaryl hyperiodonium salt (0.75mmol, 313mg) and copper salt (0.05mmol), potassium carbonate (70mg, 0.5mmol) to a 10mL Shrek tube , after replacing the nitrogen gas three times, 2.5 mL of dichloroethane was added and reacted at 50° C. for 4 h. After the reaction system was cooled, 5 mL of saturated NaHCO was added 3 The solution quenched the reaction, and then extracted three times with 30 mL ethyl acetate, combined the organic phases, washed with saturated NaCl and washed with anhydrous MgSO 4 Dry for 30 minutes, filter, and concentrate the filtrate with a rotary evaporator to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) to obtain 100 mg of the red solid product 11-phenylthiopyranoindole with a purity greater than 99%, and the isolated yield was 64%.

[0036] Structural ...

Embodiment 2

[0041] Embodiment 2: 3-methyl-11-phenylbenzothiopyranoindole (R in structural formula I 6 = methyl, R 9 = phenyl)

[0042] Add o-alkynyl isothiocyanate (0.5mmol, 124mg), diaryl hyperiodonium salt (0.75mmol, 313mg) and copper salt (0.05mmol), potassium carbonate (70mg, 0.5mmol) to a 10mL Shrek tube , after replacing the nitrogen gas three times, 2.5 mL of dichloroethane was added and reacted at 50° C. for 4 h. After the reaction system was cooled, 5 mL of saturated NaHCO was added 3 The solution quenched the reaction, and then extracted three times with 30 mL ethyl acetate, combined the organic phases, washed with saturated NaCl and washed with anhydrous MgSO 4 Dry for 30 minutes, filter, and concentrate the filtrate with a rotary evaporator to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) to obtain 99 mg of 3-methyl-11-phenylbenzothiopyranoindole as a red solid product with a purity of more than 99%, and the isol...

Embodiment 3

[0048] Embodiment 3: 2-methyl-11-phenylbenzothiopyranoindole (R in structural formula I 7 = methyl, R 9 = phenyl)

[0049] Add o-alkynyl isothiocyanate (0.5mmol, 124mg), diaryl hyperiodonium salt (0.75mmol, 313mg) and copper salt (0.05mmol), potassium carbonate (70mg, 0.5mmol) to a 10mL Shrek tube , after replacing the nitrogen gas three times, 2.5 mL of dichloroethane was added and reacted at 50° C. for 4 h. After the reaction system was cooled, 5 mL of saturated NaHCO was added 3 The solution quenched the reaction, and then extracted three times with 30 mL ethyl acetate, combined the organic phases, washed with saturated NaCl and washed with anhydrous MgSO 4 Dry for 30 minutes, filter, and concentrate the filtrate with a rotary evaporator to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) to obtain 100 mg of a red solid product 2-methyl-11-phenylbenzothiopyranoindole with a purity of more than 99%, and the isolat...

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Abstract

The invention discloses a preparation method of a polysubstituted thiapyran diindyl derivative, which belongs to the technical field of pharmaceutical synthesis and photoelectric material synthesis. The method comprises the steps of adding diaryl hypervalent iodonium salts, o-alkynyl isothiocyanate, potassium carbonate and copper salt into a reactor, pumping and injecting nitrogen for three times, adding a solvent, and heating until a reaction is over; adding water or a salt solution for a quenching reaction after cooling a system, performing extraction by using ethyl acetate separately for three times, combining organic phases, adding magnesium sulfate for drying, filtering, concentrating filtrate by a rotary evaporator to obtain a crude product, and performing column chromatography isolation by using an eluent to obtain a product. The preparation method of the polysubstituted thiapyran diindyl derivative, provided by the invention, is scientific and reasonable, and higher in yield, and the product is easy to purify.

Description

technical field [0001] The invention belongs to the technical fields of drug synthesis and photoelectric material synthesis, and in particular relates to a preparation method of multi-substituted thiopyranoindole derivatives. Background technique [0002] Indole derivatives are a common class of heterocyclic compounds widely present in natural products with biological and pharmacological activities, such as quinine, strychnine and other natural products. Many thiopyranoindole derivatives have biological and pharmacological activities such as bactericidal, antihypertensive, antidepressant, antiallergic, and antitumor. [0003] With the continuous development of organic synthetic chemistry, the synthetic application of indole fused heterocyclic derivatives has gone beyond the field of medicine, and gradually extended to metal organic chemistry, asymmetric organic synthetic chemistry, material chemistry and many other fields. In recent years, many indole fused heterocyclic der...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 文丽荣沈强玉郭维斯李明
Owner QINGDAO UNIV OF SCI & TECH
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