Intramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines

A thermally induced intramolecular annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined. The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbene...

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Bibliographic Details
Published in:Tetrahedron Vol. 59; no. 44; pp. 8775 - 8791
Main Authors: Söderberg, Björn C.G, Shriver, James A, Cooper, Seth H, Shrout, Timothy L, Scott Helton, E, Austin, Lucinda R, Odens, Herman H, Hearn, Brian R, Jones, Paula C, Kouadio, Tiara N, Ngi, Tan H, Baswell, Rachel, John Caprara, H, Meritt, Mark D, Mai, Than T
Format: Journal Article
Language:English
Published: Elsevier Ltd 27-10-2003
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Summary:A thermally induced intramolecular annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined. The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.09.028