One-Pot Friedländer Quinoline Synthesis: Scope and Limitations

Abstract A highly effective one-pot Friedländer quinoline synthesis from O-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The O-nitroarylcarbaldehydes were reduced to O-aminoarylcarbaldehydes with iron in the presence of a cat...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2010-05, Vol.2010 (10), p.1678-1686
Main Authors: Li, An-Hu, Beard, David J., Coate, Heather, Honda, Ayako, Kadalbajoo, Mridula, Kleinberg, Andrew, Laufer, Radoslaw, Mulvihill, Kristen M., Nigro, Anthony, Rastogi, Pawan, Sherman, Dan, Siu, Kam W., Steinig, Arno G., Wang, Ti, Werner, Doug, Crew, Andrew P., Mulvihill, Mark J.
Format: Article
Language:English
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Summary:Abstract A highly effective one-pot Friedländer quinoline synthesis from O-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The O-nitroarylcarbaldehydes were reduced to O-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono- or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1218701