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Nickel‐Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides
Author(s) -
Stolley Ryan M.,
Maczka Michael T.,
Louie Janis
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100428
Subject(s) - chemistry , cycloaddition , catalysis , yield (engineering) , regioselectivity , nickel , aminopyridines , intermolecular force , bicyclic molecule , medicinal chemistry , 2 aminopyridine , functional group , combinatorial chemistry , organic chemistry , molecule , materials science , polymer , metallurgy
A variety of bicyclic N , N ‐disubstituted 2‐aminopyridines have been prepared from diynes and cyanamides by nickel‐catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2‐aminopyridines in good to excellent yields. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides with diverse functional group tolerance were used. The intermolecular version employing 3‐hexyne and N ‐cyanopyrrolidine also afforded the desired N , N ‐disubstituted 2‐aminopyridine in good yield.