Palladium-catalyzed amination in the synthesis of macrocyclic compounds containing 1,3-disubstituted adamantane fragments

Palladium-catalyzed amination of 1,3-dibromobenzene, 2,6-dibromopyridine, 3,3′-dibromobiphenyl, 2,7-dibromonaphthalene, and 1,8-dichloroanthracene with an equimolar amount of 2,2′-(adamantane-1,3-diyl)diethanamine resulted in the formation of macrocyclic compounds containing one or several adamantan...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2009-10, Vol.45 (10), p.1555-1566
Main Authors: Ranyuk, E. R, Averin, A. D, Buryak, A. K, Savel'ev, E. N, Orlinson, B. S, Novakov, I. A, Beletskaya, I. P
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Palladium-catalyzed amination of 1,3-dibromobenzene, 2,6-dibromopyridine, 3,3′-dibromobiphenyl, 2,7-dibromonaphthalene, and 1,8-dichloroanthracene with an equimolar amount of 2,2′-(adamantane-1,3-diyl)diethanamine resulted in the formation of macrocyclic compounds containing one or several adamantane and one or several aromatic fragments. The reactions of 2,2′-(adamantane-1,3-diyl)diethanamine with excess 1,3-dibromobenzene, 2,6-dibromopyridine, 1,8-dichloroanthracene, and 1,8-dichloroanthraquinone gave the corresponding N,N′-diaryl derivatives. Polyaza macrocycles incorporating adamantane, aromatic, and 4,7,10-trioxatridecane-1,13-diamine fragments, were obtained by palladium-catalyzed amination of the N,N′-diaryl derivatives with 4,7,10-trioxatridecane-1,13-diamine.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428009100236