Catalytic Heterocyclization Reactions in the Synthesis of N-substituted Dithiazacyclanes, Crown-like Macrocycles and Polyazapolycycles
Year: 2025
Type: article
Abstract: Saturated O,S,N-containing hetero(poly)cycles are of particular interest among a wide variety of heterocyclic compounds due to their pronounced biological activity and prospects for practical application. These compounds demonstrate high potential in the development of drugs with anti-inflammatory, antibacterial, antifungal and cytotoxic properties. Modern methods of catalytic synthesis open up new possibilities for single-reactor design of functionally substituted hetero(poly)cycles under mild conditions. Catalytic heterocyclization is a powerful tool for the targeted synthesis of complex organic structures with a given molecular architecture, allows the use of available starting reagents, and ensures the selectivity of reactions and a high yield of target products. This review systematizes the results of research in the field of catalytic synthesis of N-substituted dithiazacyclanes, crown-like macrocycles and polyazapolycycles. These works was initiated in 2009 by Askhat Gabdrakhmanovich Ibragimov, Doctor of Chemical Sciences, Professor. Within the framework of fundamental research conducted in the Labora tory of Heteroatomic Compounds of the Institute of Petrochemistry and Catalysis under the leadership of A.G. Ibragimov, new methods for the synthesis of heteroatom-containing compounds were developed, as well as potential areas of their application were studied. Special attention was paid to the use of salts of d- and f-elements as catalysts, which made it possible to significantly expand the range of synthesized hetero(poly)cycles. One of the key achievements was the development of a method for the catalytic heterocyclization of azabicyclanes with cycloaminomethylating reagents. This approach ensures the transformation of one heterocyclic fragment into another by including structural elements of cycloaminomethylating reagents, which makes it possible to obtain complex molecular ensembles in one preparative stage. The proposed catalytic methods are universal and can be applied to the synthesis of hetero(poly)cycles with different functional groups. This work makes a significant contribution to the development of methods for the directed synthesis of complex heterocyclic compounds and opens up new prospects for their study in practice.
Authors: E.B. Rakhimova, V.Yu. Kirsanov
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4411461614