Synfacts 2011(1): 0029-0029  
DOI: 10.1055/s-0030-1259206
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Multicomponent Synthesis of Azaphenanthreneamides

Contributor(s): Victor Snieckus, Johnathan Board
L.-Y. Zeng, C. Cai*
Nanjing University of Science and Technology, P. R. of China
Further Information

Publication History

Publication Date:
21 December 2010 (online)


Reported is the iodine-mediated multicomponent synthesis of azaphenanthrene­amides from naphthylamines, aromatic aldehydes, primary amines, and diketene. Four new bonds are formed and a heterocyclic ring is annulated in a one-pot reaction to afford impressive yields of products. This new reaction has all the usual benefits of multicomponent reactions, most notably high atom economy. It also uses inexpensive and readily available starting materials. Refreshingly, the authors state that the mechanism is unclear (due to the reaction giving aromatic products in the absence of oxygen), although a reasonable one could be postulated.