126947-67-9Relevant academic research and scientific papers
Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines
Abel,Averin,Anokhin,Maloshitskaya,Butov,Savelyev,Orlinson,Novakov,Beletskaya
, p. 301 - 308 (2015)
Copper(I)-catalyzed N-heteroarylation of a wide series of adamantane-containing amines with 2-bromo- and 2- and 3-iodopyridines was studied. The corresponding N-pyridyl derivatives were formed in all cases, but iodopyridines were considerably more reactive. The best results were obtained with the catalytic system CuI-2-(2-methyl-1-oxopropyl)cyclohexanone-DMF which ensured up to 90% yield of the target products. The yield of N-pyridyl derivatives also depended on the steric environment of the amino group in the initial adamantane-containing amine. The yield of the heteroarylation products can be considerably increased using excess iodopyridine. The reaction of 2-(adamantan-1-yl)ethanamine with 2,6-dibromopyridine successfully afforded the corresponding diamine, and N,N′-dipyridyl derivatives were obtained in high yields from 2,2′-(adamantane-1,3-diyl)diethanamine.
Arylation of adamantanamines: VI. Palladium-catalyzed arylation of amines and diamines of the adamantane series with 3-bromopyridine
Averin,Baranova,Abel,Kovalev,Buryak,Butov,Savelyev,Orlinson,Novakov,Beletskaya
, p. 1 - 7 (2013/03/28)
Palladium-catalyzed amination of 3-bromopyridine with amines of the adamantane series in the presence of Pd(dba)2/L [L = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl or 2-dimethylamino- 2′-dicyclohexylphosphinobiphenyl] gave the desired N-(pyridin-3-yl)- substituted amines in 74-97% yields. Diamines of the adamantane series reacted with 2 equiv of 3-bromopyridine in a complicated fashion to produce mono- and triaryl-substituted derivatives as by-products, while the yields of N,N′-diarylation products were 18-56%.
