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N-(Het)arylation of adamantane-containing amines with halonaphthalenes and haloquinolines catalyzed by either CuI or copper nanoparticles with an average size of 25 nm in the presence of 2-isobutyrylcyclohexanone, rac-BINOL, and l-proline as a ligand and Cs2CO3 as a base in DMSO at 110 °C was studied. The reactions proceed smoothly with 2-iodonaphthalene and 6-iodoquinoline, the possibility of successful reactions with 6- and 3-bromoquinolines was also shown. In the case of 1-bromonaphthalene, 5- and 8-bromoquinolines, only Pd-catalyzed amination can provide the high yields of the products. An alternative possibility of C(sp2)—N bond formation was studied employing the Chan—Lam reaction with of 2-naphthaleneboronic acid and pinacolates of 6- and 3-quinolineboronic acids. [ABSTRACT FROM AUTHOR]

The regularities of the reduction of unsaturated nitriles containing the 2-adamantyl fragment with lithium aluminum hydride and nickel—aluminum alloy were studied. In both cases, the double bond and nitrile group were simultaneously reduced. The presence of bulky substituents in the substrate in the α-position to the adamantyl fragment and hydroxy groups significantly retards the process, and the 80–90% yield of the corresponding products is achieved only when the temperature is raised to 65 °C. In the case of using a nickel—aluminum alloy, its 4—6-fold excess is required. The calculation of the potential pharmacological activity of the synthesized compounds shows that they can have antiviral, analgesic, and antidiabetic activity. [ABSTRACT FROM AUTHOR]

1,5-Dimethylbispidinone (1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one) reacts with natural ketones, including optically active ones, to give new aminal-type compounds combining diazaadamantane and aliphatic fragments. [ABSTRACT FROM AUTHOR]

A reaction of methyl 2-(4-allyl-2-methoxyphenoxy)acetate with adamantan-2-amine and (adamantan-1-yl)methylamine in butanol leads, together with the target amides, to the formation of butyl ester of the corresponding acid, which is resistant to aminolysis. [ABSTRACT FROM AUTHOR]

Amination of 3,6-dichloropyridazine, chloropyrazine, 2,3and 2,6-dichloropyrazines, 2-chloroquinoxaline, 1-chloroand 1,3-dichloroisoquinolines with various adamantane-containing amines characterized by different steric hindrances at the amino group was studied. The yields of the amination products depended on the structure of starting compounds. In the reactions of all the dichloroheteroarenes, selective substitution of only one chlorine atom took place, with the best yields being observed for 2,6-dichloropyrazine. In the reaction of 1,3-dichloroisoquinoline, the chlorine atom at position 1 was selectively substituted in up to 90% yield. [ABSTRACT FROM AUTHOR]

A copper(I) complex-catalyzed N, N'-diarylation of diamines based on 1,3-disubstituted adamantane, using aryl iodides bearing electron-donating and electron-withdrawing substituents, was studied. In the case of 2,2'-(adamantane-1,3-diyl)ethanediamine, the optimal catalyst system is CuI-2-(isobutyryl)cyclohexanone-CsCO-DMF. The highest yield of diarylation product was reached in the case of 4-methoxyiodobenzene (79%). In the case of more spatially hindered adamantane-1,3-diyldimethanamine, 1,1'-binaphthalene-2,2'-diol (BINOL) should be used, with the highest yield of the target product (84%) being reached in the reaction with iodobenzene. [ABSTRACT FROM AUTHOR]

Catalyst-free reactions of 2-fluoropyridine with amines and diamines bearing the adamantyl moiety at either the N atom or in the side chain were studied. Amines, which do not contain secondary alkyl substituents at the amino group, react with an excess of 2-fluoropyridine to give N-(pyridin-2-yl) derivatives in the yields from moderate to good. 2-Fluoro-5-halopyridines were found to be more reactive than 2-fluoropyridine. [ABSTRACT FROM AUTHOR]

Aminolysis of 8-chlorotheophylline with primary amines of adamantane family leads to new 8-[(adamant-1-yl)alkylamino]theophylline derivatives. Biological studies showed that one of the compounds obtained inhibited activity of recombinant HIV-1 reverse transcriptase in the concentration of 50 μmol L. [ABSTRACT FROM AUTHOR]