Synthesis of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives

Synthesis, structure, and antitumor activity of 2,9-disubstituted perhydro 2,3a,7b,9,10a,14b-hexaazadibenzotetracenes

“…The broad range of biological activities of heterocyclic molecules with the adamantane cage 35 attracts attention of researchers and stimulates development of new efficient synthetic routes to cage compounds containing various heterocyclic moieties. Therefore, our subsequent experiments were directed towards development of a selective synthesis of 2,9-diadamantyl-substituted perhydro 2,3a,7b,9,10a,14bhexaazadibenzotetracenes.…”

Recent Advances in the Chemistry of Saturated Annulated Nitrogen-Containing Polycyclic Compounds

“…The broad spectrum of biological activity of the heterosystems with an adamantane moiety [ 78 ] attracts the attention of researchers and stimulates the development of efficient methods for the synthesis of new cage molecules. In this regard, the same authors [ 73 ] performed the one-pot cyclocondensation of adamantylamines with formaldehyde and tetraazaperhydrotetracene 124 b in the presence of granulated H-Ymmm zeolite to give previously undescribed diadamantyl-substituted hexaazaperhydrodibenzotetracenes 129 ( Scheme 36 ).…”

Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp3)–H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives

“…Notably, current available adamantane analogues are largely restricted to functionalization of the bridgehead methine moieties, including alkylation, carboxylation, hydroxylation, halogenation, and amination, due to the readily formation of stable carbocations or radicals at these carbons . Unfortunately, direct diverse modifications on the bridge methylenes of the adamantane skeleton are rare . Recently, the Wang group described a palladium-catalyzed methylene C­(sp 3 )–H arylation of the adamantyl scaffold; however, the method suffered from many drawbacks, including the following: (a) low yields; (b) intolerance of heterocyclic halides; (c) narrow scope of substrates; (d) racemic arylation products .…”