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Preparation method of 2-substituted-1,3-dithiane derivative

A technology of dithiane and derivatives, applied in the field of substituting 1, which can solve problems such as complex preparation methods, limited applications, and toxicity

Inactive Publication Date: 2015-11-25
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, the preparation method of substituted 1,3-dithiane derivatives is the synthesis of 1,3-propanedithiol and aldehydes and ketones, but the odor and toxicity of 1,3-propanedithiol limit this type of reaction Applications
At present, different reagents and methods have been developed to replace 1,3-propanedithiol reagent, but most of the preparation methods are complicated, require multi-step reaction synthesis, expensive alternatives and poor atom economy, etc.

Method used

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  • Preparation method of 2-substituted-1,3-dithiane derivative
  • Preparation method of 2-substituted-1,3-dithiane derivative
  • Preparation method of 2-substituted-1,3-dithiane derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 In a 10ml round bottom flask, add 1,3-dithiane (0.250mmol), NCS (0.300mmol), add 2ml of DCE to dissolve and react at -10°C for 0.5-1h. After TLC monitoring, benzaldehyde (0.250 mmol) and ferric chloride (0.025 mmol) were added after the reaction was complete, and the reaction was continued for 12 hours. After TLC detection, the solvent was evaporated after the reaction was complete, and the product was obtained by column chromatography.

Embodiment 3

[0020] Example 3 In a 10 ml round bottom flask, add 1,3-dithiane (0.250 mmol), NCS (0.300 mmol), add 2 ml of DCE to dissolve and react at -10°C for 0.5 to 1 h. After TLC monitoring, after the reaction was complete, p-methoxybenzaldehyde (0.250 mmol) and boron trifluoride ether (0.025 mmol) were added, and the reaction was continued for 4 h. After TLC detection, the solvent was evaporated after the reaction was complete, and the product was obtained by column chromatography.

[0021] Implementation 40 In a 10 ml round bottom flask, add 1,3-dithiane (0.250 mmol), NCS (0.300 mmol), add 2 ml of DCE to dissolve and react at -10°C for 0.5 to 1 h. After TLC monitoring, n-butyraldehyde (0.250 mmol) and ferric chloride (0.025 mmol) were added after the reaction was complete, and the reaction was continued for 8 h. After TLC detection, the solvent was evaporated after the reaction was complete, and the product was obtained by column chromatography.

Embodiment 44

[0022] Example 44 In a 10 ml round bottom flask, 1,3-dithiane (0.250 mmol) and NCS (0.300 mmol) were added, 2 ml of DCE was added to dissolve, and reacted at -10° C. for 0.5 to 1 h. After TLC monitoring, after the reaction was complete, crotonaldehyde (0.250 mmol) and ferric chloride (0.025 mmol) were added, and the reaction was continued for 8 h. After TLC detection, the solvent was evaporated after the reaction was complete, and the product was obtained by column chromatography.

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Abstract

The invention provides a preparation method of a 2-substituted-1,3-dithiane derivative. The preparation method comprises the following steps: adding 1,3-dithiane (CAS:505-23-7) and 1,2-dichloroethane (DCE) or dichloromethane (DCM) into a reaction bottle, adding N-chlorosuccinimide (NCS) under ice-bath condition, and stirring for 0.5-1 h to prepare a 2-chloro-1,3-dithiane solution; and adding an aldehyde or ketone compound and a lewis acid catalyst into the above solution, and reacting to prepare the 2-substituted-1,3-dithiane derivative. By using the 1,3-dithiane solid and different types of aldehyde and keto-carbonyl compounds as raw material and using one or more of ferric trichloride, boron trifluoride diethyl etherate, methanesulfonic acid, aluminum trichloride, ferrous chloride and nickel chloride as catalysts, preparation of the 2-substituted-1,3-dithiane derivative is realized. The catalysts used in the invention are cheap and easily available, dosage of the catalysts is low and pollution of the catalysts is little. The solid raw materials used in the invention can avoid use of fetid toxic 1,3-dimercaptopropane with strong volatility, and the purpose of protecting an experimenter's body and reducing environmental pollution is realized. In addition, the preparation method has advantages of mild reaction condition, high yield, simple operation and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method for substituted 1,3-dithiane derivatives. Background technique [0002] 1,3-Dithiane (1,3-dithiane) derivatives are important organic functional group reagents. 1,3-Dithiane can not only be used in the synthesis of aldehydes and ketones and as a protecting group for carbonyl groups in organic synthesis, but also can be used in the preparation of multifunctional carbonyl compounds to construct complex molecular skeletons and complex molecular fragments, thereby achieving many Total synthesis and preparation of target molecules, pharmaceutical molecules and natural products. Secondly, 1,3-dithiane can participate in the research of many organic reactions, such as: Linchpin reaction, Brook rearrangement reaction, ARC (Anion Relay Chemistry) reaction and carbolithiation reaction, etc. Usually, the preparation method of substituted 1,3-dithiane derivat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/08
CPCC07D339/08
Inventor 唐寿初赖俊汕杜文斌田丽霞
Owner LANZHOU UNIVERSITY
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