Synthetic method of lactam compound

Abstract

The invention discloses a synthesis method of a lactam compound. The synthesis method comprises the following steps: (1) dissolving N-F benzenesulfonamide and acyl chloride in an organic solvent under the protection of gas, conducting uniform stirring, and conducting reacting to obtain a crude product; (2) recrystallizing the crude product to obtain a product A; (3) dissolving the product A obtained in the step (2), cuprous iodide and phenanthroline in a mixed organic solvent, and conducting heating for a reaction to obtain an intermediate; and (4) dissolving the intermediate, adding tetrabutylammonium fluoride, and performing stirring to obtain a target product. According to the invention, commercially available N-F benzenesulfonamide and acyl chloride are used as starting raw materials, and the materials are easy to obtain; according to the synthesis method disclosed by the invention, the commercially cheap and easily available cuprous iodide is selected as a catalyst, so the use of an expensive noble metal catalyst is avoided, and economical efficiency is effectively improved; the whole synthesis method disclosed by the invention is mild in reaction conditions; and the target compound is obtained through free radical cyclization, the use of other oxidizing agents or noble metal catalysts is avoided, and synthesis cost is low.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a synthesis method of a five-membered or six-membered ring lactam compound. Background technique [0002] In heterocyclic compounds, the lactam structure is an extremely important part and widely exists in various natural products and drug molecules. Some lactam compounds have good biological activity, and have been verified to have antibacterial, antiviral and anti-senile dementia effects. For example, HIV-1 protease inhibitors containing a γ-lactam structure have good water solubility and pharmacological activity. As an important intermediate in organic synthesis, valerolactam has also attracted the attention of chemists. It has been reported that inhibitors containing valerolactam structures exhibit good activity. Therefore, it is of great significance to find an efficient scheme to synthesize five-membered or six-membered cyclic lactam compounds. [0003] At pr...

AI Technical Summary

Problems solved by technology

However, these schemes all have certain disadvantages, such as the method of synthesizing γ-lactam by β-lactam ring expansion is limited to specific substrate types, and needs to use stronger bases (LDA, etc.), which is It brings great inconvenience and pollution; 4+1 cyclization or other cyclization methods need to use more expensive catalysts or require higher temperatures; for transition metal catalysis to obtain lactam compound solutions, most of them are obtained through Catalyzed by precious metals such as rhodium (Rh), iridium (Ir), palladium (Pd), gold (Au), etc., and generally need to be carried out at 50-70°C

Although the above schemes have achieved the preparation of a series of five-membered or six-membered ring lactam compounds, they all have certain limitations or require the use of more expensive catalysts

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