A kind of preparation method of 3-indolated cyclohexenone compound

A technology of cyclohexenone and compound is applied in the field of preparation of indoleated cyclohexenone derivatives, and achieves the effects of simple reaction steps, mild reaction conditions and improved total yield

Active Publication Date: 2022-05-31
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the transition metal-catalyzed direct coupling reaction between cyclohexenone and heterocyclic C-H / C-H bonds to construct 3-heterocyclylcyclohex-2-enone derivatives is still unresolved

Method used

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  • A kind of preparation method of 3-indolated cyclohexenone compound
  • A kind of preparation method of 3-indolated cyclohexenone compound
  • A kind of preparation method of 3-indolated cyclohexenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of 3-(1H-indol-3-yl)cyclohex-2-enone

[0042] (1) Indole (0.0293g, 0.25mmol), cyclohexenone (0.097mL, 1mmol), palladium trifluoroacetate (0.0083g, 0.025mmol), 2,5-dimethyl-8-trifluoromethane yl-3,4-dihydro-2H-pyrano[2,3-b]quinoline (0.0141 g, 0.05 mmol), tert-butanol peroxide (0.075 mL, 0.375 mmol), dimethyl sulfoxide (0.8 mL), tetrahydrofuran (0.4 mL), stirred evenly in a dry and clean airtight reaction tube, heated to 50° C., and reacted for 24 hours.

[0043](2) After the reaction was completed, the reaction tube was cooled to room temperature, 50 mL of ethyl acetate was added to dilute the reaction solution and transferred to a 100 mL separatory funnel, 10 mL of saturated brine was added, shaken, and allowed to stand, and the organic phase and the aqueous phase were separated, The aqueous phase was then extracted twice with 30 mL of ethyl acetate, the resulting organic phases were combined and dried over anhydrous sodium sulfate, the solvent wa...

Embodiment 2

[0044] Example 2: Synthesis of 3-(1-methyl-indol-3-yl)cyclohex-2-enone

[0045] (1) 1-methylindole (0.031 mL, 0.25 mmol), cyclohexenone (0.097 mL, 1 mmol), palladium trifluoroacetate (0.0083 g, 0.025 mmol), 2,5-dimethyl-8 - trifluoromethyl-3,4-dihydro-2H-pyrano[2,3-b]quinoline (0.0141 g, 0.05 mmol), tert-butanol peroxide (0.075 mL, 0.375 mmol), dimethyl Sulfoxide (0.8 mL) and tetrahydrofuran (0.4 mL) were stirred uniformly in a dry and clean closed reaction tube, and then heated to 50° C. and reacted for 24 hours.

[0046] (2) After the reaction was completed, the reaction tube was cooled to room temperature, 50 mL of ethyl acetate was added to dilute the reaction solution and transferred to a 100 mL separatory funnel, 10 mL of saturated brine was added, shaken, and allowed to stand, and the organic phase and the aqueous phase were separated, The aqueous phase was then extracted twice with 30 mL of ethyl acetate, the resulting organic phases were combined and dried over anhyd...

Embodiment 3

[0047] Example 3: Synthesis of 3-(7-Methoxy-1H-indol-3-yl)cyclohex-2-enone

[0048] (1) 7-methoxyindole (0.033 mL, 0.25 mmol), cyclohexenone (0.097 mL, 1 mmol), palladium trifluoroacetate (0.0083 g, 0.025 mmol), 2,5-dimethyl -8-Trifluoromethyl-3,4-dihydro-2H-pyrano[2,3-b]quinoline (0.0141 g, 0.05 mmol), tert-butanol peroxide (0.075 mL, 0.375 mmol), bis Methyl sulfoxide (0.8 mL) and tetrahydrofuran (0.4 mL) were stirred uniformly in a dry and clean closed reaction tube, and then heated to 50° C. to react for 24 hours.

[0049] (2) After the reaction was completed, the reaction tube was cooled to room temperature, 50 mL of ethyl acetate was added to dilute the reaction solution and transferred to a 100 mL separatory funnel, 10 mL of saturated brine was added, shaken, and allowed to stand, and the organic phase and the aqueous phase were separated, The aqueous phase was then extracted twice with 30 mL of ethyl acetate, the resulting organic phases were combined and dried over an...

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Abstract

The invention belongs to the technical field of preparation methods of indolated cyclohexenone derivatives, and specifically relates to a preparation method of 3-position indolated cyclohexenone compounds. The steps are as follows: molar ratio 1:4:0.1:0.2 :1.5 Indole or substituted indole, cyclohexenone, palladium trifluoroacetate, 2,5-dimethyl-8-trifluoromethyl-3,4-dihydro-2H-pyrano[2 ,3‑b] Add quinoline and tert-butanol peroxide into the reactor, add solvent to dissolve and mix well, react at 50°C for 24 to 41 hours; after the reaction is completed, cool to room temperature, dilute the reactant and wash with saturated aqueous sodium chloride solution , separating the organic phase from the aqueous phase, extracting the aqueous layer with ethyl acetate, combining the organic phases, filtering, and spinning off the solvent; separating and purifying the residue after spinning off the solvent, spinning off the solvent, and pumping dry to obtain the target product. The preparation method has the advantages of cheap and easy-to-obtain raw materials, simple reaction steps, high atom utilization rate and the like.

Description

technical field [0001] The invention belongs to the technical field of preparation methods of indoleated cyclohexenone derivatives, in particular to a preparation method of a 3-position indoleated cyclohexenone compound. Background technique [0002] Compounds containing indole skeleton structures are widely used in the synthesis of natural products and drug molecules [see: (a) J.Nat.Prod.2005,68,711-715; (b)Chem.Rev.2010,110,4489-4497 .], its introduction into the C3-position of cyclohexenone by a palladium-catalyzed C-H bond activation strategy is of great significance for new drug development, and the 3-substituted cyclohexenone can be used as an important intermediate to transform into conventional synthetic methods Difficult to prepare (due to strong ortho, para-positioning effects of hydroxyl groups) resorcin [see: (a) Green Chem., 2016, 18, 6462-6467; (b) Angew. Chem. Int. Ed. 2013, 52 , 3672-3675.]. However, the synthesis of 3-substituted cyclohex-2-enone compounds...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 文振康武晓雪葛晓敏刘宇芳
Owner SHANXI UNIV
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