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Synfacts 2008(9): 0915-0915
DOI: 10.1055/s-2008-1078609
DOI: 10.1055/s-2008-1078609
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Mild Complementary Cycloisomerization Reactions to N-Fused Heterocycles
I. V. Seregin, A. W. Schammel, V. Gevorgyan*
University of Illinois at Chicago, USA
Further Information
Publication History
Publication Date:
22 August 2008 (online)
Significance
Reported are two mild and complementary cycloisomerization (A) and cascade 1,2-migration-cycloisomerization (B) processes, resulting in the formation of fused 1,3- and 1,2-substituted N-heterocycles. After a thorough screening of metal catalysts, the former was found to be efficiently catalyzed by AgBF4 and the latter by AuBr3. The yields range from modest to excellent and the substrate scope was well studied. Starting materials are easily synthesized from the corresponding heterocyclic aldehydes and propargylic Grignard reagents. Of two mechanistic pathways considered, support for one of these was obtained by deuterium-labeling and kinetic-isotope-effect studies.