The synthetic method of middle ring lactam compound

Abstract

The invention relates to a synthetic method of a medium-ring lactam compound. The synthetic method comprises the following step that an amide compound with the structure shown in the formula (I) is electrolyzed to obtain the medium-ring lactam compound with the structure shown in the formula (II). The lactam compound can be directly electrolyzed through an electrochemical method, so that the medium-ring lactam compound can be obtained. Application of a transition metal catalyst and a stoichiometric oxidizing agent is avoided, generation of chemical waste is avoided, and the atom economy is facilitated. The method is simple to operate, the product purity is high, purification is easy, the efficiency and yield are high, and the production cost is low; besides, reaction conditions are mild, inert gas protection is not needed, a reaction system is greener, environmentally friendly, safe, economical, capable of saving energy and protecting the environment, and more beneficial to industrial production.

Description

[0001] field of invention [0002] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing mesocyclic lactam compounds. Background technique [0003] Mesocyclic lactam compounds (7-11 membered rings) widely exist in natural products and biologically active molecules, especially in antibacterial and antitumor active molecules. However, there are still great challenges in the rapid and efficient synthesis of ring lactam skeletons. Therefore, it is urgent to develop new ring expansion reactions to meet the needs of drug development. [0004] Xin-Yuan Liu et al. (Wang, N.; Gu, Q.-S.; Li, Z.-L.; Li, Z.; Guo, Y.-L.; Guo, Z.; Liu, X. -Y.Angew.Chem.2018,130,14421-14425.) reported a method for photocatalytic synthesis of cyclic lactam compounds, but this method requires the use of transition metal photocatalyst ruthenium and 1.5 times the equivalent of chemical oxidants Hypervalent iodine, and the reaction needs to be ...

AI Technical Summary

Problems solved by technology

However, there are still great challenges in the rapid and efficient synthesis of the ring lactam skeleton. Therefore, it is urgent to develop new ring expansion reactions to meet the needs of drug development.

[0004] Xin-Yuan Liu et al. (Wang, N.; Gu, Q.-S.; Li, Z.-L.; Li, Z.; Guo, Y.-L.; Guo, Z.; Liu, X. -Y.Angew.Chem.2018,130,14421-14425.) reported a method for photocatalytic synthesis of cyclic lactam compounds, but this method requires the use of transition metal photocatalyst ruthenium and 1.5 times the equivalent of chemical oxidants Hypervalent iodine, at the same time, the reaction needs to be carried out under blue light irradiation conditions in an inert atmosphere

This reaction uses a metal catalyst, which leads to the easy introduction of trace amounts of heavy metals in the drug synthesis, which greatly increases the difficulty of drug purification and brings greater trouble to the subsequent purification process; at the same time, the reaction uses an equivalent amount of hypervalent iodine as an oxidant. The waste is serious, and at the same time, it is harmful to the environment, and the experimental operation is relatively dangerous

[0005] At present, there are no domestic and foreign literature reports on the synthesis of mesocyclic lactam compounds by electrochemical methods.

Images