Heating with adamantyl bromide

To a mixture of adamantyl bromide (0.5 mmol) and trifluoroacetate salt of lepidine (2.5 mmol) in benzene (6 ml) were added (trimethylsilyl)silane (1.0 mmol) and AIBN (1.0 mmol). The mixture was heated at 80 °C for 14 h under an argon atmosphere. After the reaction, the reaction mixture was washed with sat. aq. NaHC03. The organic layer was dried over Na2S04. After removal of the solvent, the residue was chromatographed on silica gel to give 2-(l-adamantyl)-4-methylquinoline in 90% (125 mg) yield [33]. 

Heating 5-methylpyrazol-3-one 11 with 1-adamantyl bromide 27 at 150 °C afforded 2-adamantylpyrazol-3-one 28, whereas at 200 °C 4-adamantylpyrazol-3-one 29 was obtained (99BSB735) (Scheme 9). 

Adamantyl bromide heated 20 min. at 100° with excess coned, ethereal methyl-magnesium bromide in an aerosol pressure bottle -> 1-methyladamantane. Y ... 

In [37], synthesis of the first representatives of the corresponding adamantylsubstituted bicyclic systems - 2-(l-adamantyl)imidazo[2,l-a]pyridine (29) and 2-(l-adamantyl)imidazo[2,l-b]thiazole (30), by the reaction of bromomethyl 1-adamantyl ketone with 2-aminopyridine and 2-aminothiazole correspondingly was presented. It was found that on heating the mixture in absolute alcohol, the reaction proceeds through the intermediate formation of hydrobromides 2-amino-3-(l- adamantoyl-methyl)pyridinium and 2-amino-3-(l-adamantoylmethyl)thiazoliiun, bromides, which were converted into compounds 29 and 30 by heating in a sodium hydroearbonate solution [37],... 

---