Thioamide compound and compounding method thereof

Abstract

The invention discloses a compounding method for a thioamide compound shown as formula (II). The compounding method comprises the following steps: by taking aldehyde and formyl aliphatic amine as reacting raw materials and taking Na2S.9H2O as a sulfuration reagent, reacting in a water phase under an effect of an oxidizing agent, thereby acquiring the thioamide compound. The compounding method provided by the invention has the advantages that the raw materials are low in cost and are easily acquired, the solvents are green and environment-friendly, the reaction operation is simple, the condition is mild, the substrate is wide in universality, the yield is higher, the functional group tolerance is excellent, the thioamide modification for natural aldehyde and biological active molecule is successively realized, and a method for efficiently constructing the thioamide compound is supplied to the medicinal chemical and biologic orthogonal chemical research.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and specifically relates to thioamide compounds and their synthesis methods. Background technique [0002] Thioamide compounds are a very important class of compounds, which are widely used as various drugs and biologically active molecules, as shown in formulas (i) to (iii). Therefore, it is particularly important to construct thioamide compounds starting from some compounds with simple structures and commercially available in large quantities. [0003] [0004] Drug molecules containing thioamide structure [0005] The traditional method of synthesizing thioamides is mainly through amides and Lawson's reagent or phosphorus pentasulfide. In this type of method, the Lawson's reagent used is unstable, relatively expensive, low in atom economy, and has a large odor, and has various degrees of damage to the environment and the human body. The required amid...

AI Technical Summary

Problems solved by technology

In this type of method, the Lawson's reagent used is unstable, relatively expensive, low in atom economy, and has a large odor, and has various degrees of damage to the environment and the human body. The required amide must be passed through carboxylic acid (or acid chloride) in advance ) and amine condensation preparation, low step economy

In recent years, a method for preparing thioamides using the Willgerodt-Kindler reaction has been developed. This method uses sulfur as a sulfur source, and aryl aldehydes, aryl / alkyl ketones, aryl acetylenes, benzylamines, and aryl acetic acids etc. as raw materials to synthesize thioamide compounds. Compared with the traditional method, this method improves the atom utilization rate and step economy, but the universality of the substrate is not wide, and the reaction conditions of some substrates are harsh, and the reaction temperature can reach up to 320 ° C , many raw materials are not easy to obtain, and the use of organic solvents also limits its practicality

Many of the above deficiencies restrict the in-depth application of such methods in the field of process research and medicinal chemistry research.

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