Synfacts 2006(7): 0660-0660  
DOI: 10.1055/s-2006-941844
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Pyridine and Quinoline Derivatives via Ru-Catalyzed Cyclization of Azadienynes

Contributor(s): Snieckus, Wei Gan
M. Movassaghi*, M. D. Hill
Massachusetts Institute of Technology, Cambridge, USA
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Publikationsverlauf

Publikationsdatum:
22. Juni 2006 (online)

Significance

A mild and efficient two-step procedure for the synthesis of pyridine and quinoline derivatives from readily available N-vinyl or N-aryl amides is presented. The use of 2-chloropyridine as the base was found to be crucial for the conversion of starting amides (including sensitive N-vinyl amides) to the corresponding C-silyl alkynyl imines. The combination of SPhos and CpRu(PPh3)2Cl was found to be the optimal catalytic system for the desilylative cycloisomerization to give the pyridine and quinoline derivatives in good to excellent yields.