1,3-DEHYDROADAMANTANE AND ITS DERIVATIVES: A VERSATILE SYNTHETIC PLATFORM FOR PREPARATION OF FUNCTIONAL COMPOUNDS WITH A CAGE STRUCTURE. A REVIEW

Abstract

A promising strategy for the synthesis of a functional compounds with framework structure is using of 1,3‑dehydroadamantane (tetracyclo[3.3.1.1.3,7.0.1,3]decane, 1,3-DHA, bridging [3.3.1]propellane) and its derivatives, which are able to restoration of adamantane structure in their reactions. The review provides information on the methods for the synthesis of 1,3-DHA, spectral characteristics, probable intermediates generated from propellanes, and the advantages of using – low-stage syntheses of hardly available adamantine derivatives, atomic precision, and “green chemistry”. The reactions of 1,3-DHA with a wide range of organic compounds are considered, a comparative assessment of its reactivity with respect to CH-, NH-, OH- and SH-acids, as well as arenes, hydantoins, and heterocyclic compounds is carried out. New chemo- and regioselective methods for the one-step introduction of a 1-adamantyl group into the molecules of various substrates are classified. Particular attention is paid to the reactions of 1,3-DHA with various C–H acids, which make it possible to easily form C–CAd bonds to obtain hard-to-reach adamantane derivatives. The influence of pKa of the substrate on the selectivity of the reactions was shown. Low-step methods for the synthesis of new adamantane derivatives, which have shown high activity as hsEH epoxide hydrolase inhibitors and antitumor agents, are described.