A series of (R)- and (S)-isomers of new adamantane-substituted heterocycles (1,3-oxazinan-2-one, piperidine-2,4-dione, piperidine-2-one and piperidine) with potent activity against rimantadine-resistant strains of influenza A virus were synthesized through the transformation of adamantyl-substituted N-Boc-homoallylamines 8 into piperidine-2,4-diones 11 through the cyclic bromourethanes 9 and key intermediate enol esters 10. Biological assays of the prepared compounds were performed on the rimantadine-resistant S31N mutated strains of influenza A – A/California/7/2009(H1N1)pdm09 and modern pandemic strain A/IIV-Orenburg/29-L/2016(H1N1)pdm09. The most potent compounds were both enantiomers of the enol ester 10 displaying IC₅₀ = 7.7 μM with the 2016 Orenburg strain.

The review surveys the existing routes to piperidine-2,4-dione-type heterocycles including derivatives with the most vital types of biological activity. This heterocyclic platform is ideal for the construction of modern drugs and natural products.

Carbon dioxide is a cheap, easily available, and practically inexhaustible source of synthetic carbon (C₁-synthon). Among various transformations of CO₂, the synthesis of cyclic carbonates from epoxides and cyclic carbamates from aziridines can be referred to as priority areas in the development of contemporary chemical synthesis and catalysis. Cyclic carbonates found wide application in modern industry (electrolytes, solvents, reagents, polymers) and their use and production will be constantly increased. The development of effective catalytic processes that would allow the synthesis of carbonates under mild conditions (atmospheric pressure of CO₂ or lower, temperature 25°C) and low loads of durable and affordable catalysts is at the forefront of research. In the present review we analyze the existing directions of research on the catalytic systems based earth-abundant metals Al³⁺, Fe²⁺(³⁺), and Zn²⁺ for the synthesis of cyclic carbonates from epoxides and cyclic carbamates from aziridines.