Synfacts 2007(11): 1134-1134  
DOI: 10.1055/s-2007-991288
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Quinolines by Catalyzed Cyclodehydration of Aminoaryl-2-yn-1-ols

Contributor(s): Victor Snieckus, Toni Rantanen
B. Gabriele*, R. Mancuso, G. Salerno, G. Ruffolo, P. Plastina
Università della Calabria, Arcavacata di Rende, Italy
Further Information

Publication History

Publication Date:
24 October 2007 (online)

Significance

A general synthesis of substituted quinolines through a copper- or palladium-catalyzed 6-endo-dig annulation-dehydration of amino­aryl-2-yn-1-ols, easily prepared using readily available acetylenic Grignard reagents, is reported. The reaction may be carried out in one pot, which is of significance since the aminoaryl-2-yn-1-ols are unstable towards purification. Unfortunately, the reaction of TMS alkynes (R4 = TMS) led to a loss of the TMS group. Otherwise, the availability of TMS-substituted quinoline products may open new routes for further desilylative substitution chemistry. The scope of the reaction with respect to substitution on both reaction partners was inadequately tested.