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Method for preparing N-sulfonyl substituted tetrahydro-beta-carboline derivative

A technology for sulfonyl and derivatives, which is applied in the field of N-sulfonyl-substituted tetrahydro-β-carboline derivatives and their preparation, and achieves the effects of high yield and few reaction steps

Inactive Publication Date: 2013-05-08
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the functionalization of tetrahydro-β-carboline derivatives to synthesize polysubstituted tetrahydrocarboline derivatives still faces challenges.

Method used

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  • Method for preparing N-sulfonyl substituted tetrahydro-beta-carboline derivative
  • Method for preparing N-sulfonyl substituted tetrahydro-beta-carboline derivative
  • Method for preparing N-sulfonyl substituted tetrahydro-beta-carboline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add N-methylindole-2-methanol (0.6 mmol), 2-phenyl-1-p-toluenesulfonyl aziridine (0.5 mmol), scandium trifluorosulfonate (0.01 mmol) and ClCH2CH2Cl (3 mL), then heated to 83 °C and stirred for 2 hours (TLC monitoring). After the reaction, distilled water (10 mL) was added to terminate the reaction, extracted with ethyl acetate (30 mL × 3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was mixed with petroleum ether: ethyl acetate = 4:1 The solvent was the developing solvent, and the product (154 mg, yield: 74%) was isolated by column chromatography.

[0019] Its structural formula is:

[0020]

Embodiment 2

[0022] Add N-methylindole-2-methanol (0.6 mmol), 2-p-fluorophenyl-1-p-toluenesulfonyl aziridine (0.5 mmol), scandium trifluorosulfonate (0.01 mmol) to the reaction flask in sequence ), ClCH2CH2Cl (3 mL), then heated to 83 °C and stirred for 2 hours (monitored by TLC). After the reaction, distilled water (10 mL) was added to terminate the reaction, extracted with ethyl acetate (30 mL × 3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was mixed with petroleum ether: ethyl acetate = 4:1 The solvent was a developing solvent, and the product (167 mg, yield: 77%) was isolated by column chromatography.

[0023] Its structural formula is:

[0024]

Embodiment 3

[0026] Add N-methylindole-2-methanol (0.6 mmol), 2-p-chlorophenyl-1-p-toluenesulfonyl aziridine (0.5 mmol), scandium trifluorosulfonate (0.01 mmol) to the reaction flask in turn ), ClCH2CH2Cl (3 mL), then heated to 83 °C and stirred for 2 hours (monitored by TLC). After the reaction, distilled water (10 mL) was added to terminate the reaction, extracted with ethyl acetate (30 mL × 3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was mixed with petroleum ether: ethyl acetate = 4:1 The solvent was a developing solvent, and the product (169 mg, yield: 75%) was isolated by column chromatography.

[0027] Its structural formula is:

[0028]

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PUM

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Abstract

The invention discloses a method for preparing an N-sulfonyl substituted tetrahydro-beta-carboline derivative. The N-sulfonyl substituted tetrahydro-beta-carboline derivative is synthesized by using trifluorosulfoacid salt to catalyze the reaction of substituted indol-2-methanol and substituted sulfonyl ethylene imine. Compared with the prior art, the method has the advantages of a few reaction steps and high yield.

Description

technical field [0001] The present invention relates to substituted tetrahydrocarboline derivatives, specifically a class of N-sulfonyl substituted tetrahydro-β-carboline derivatives and a preparation method thereof. Background technique [0002] Tetrahydrocarboline derivatives widely exist in natural products, are a class of important physiologically active substances, and are widely used in medicine. The Pictet-Spengler condensation reaction of tryptophan with aliphatic or aromatic aldehydes is an important method for the synthesis of tetrahydrocarboline derivatives (A. Pictet, T. Spengler, Ber. Dtsch. Chem. Ges. 1911, 44, 2030; I. T Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404). However, the functionalization of tetrahydro-β-carboline derivatives to synthesize polysubstituted tetrahydrocarboline derivatives still faces challenges. The use of palladium-catalyzed intramolecular cyclization of allyl-substituted tryptamines can ef...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 王绍武王少印周双六柴卓
Owner ANHUI NORMAL UNIV
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