A Revisit to the Hantzsch Reaction: Unexpected Formation of Tetrahydro­benzo[b]pyrans beyond Polyhydroquinolines

Abstract A competitive multicomponent synthesis of tetrahydrobenzo[B]pyrans over polyhydroquinolines is achieved in the presence of ammonium acetate at ambient temperature in ethanol medium. The formation of tetrahydrobenzo[B]pyran instead of polyhydroquinoline in solution phase has been confirmed b...

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Bibliographic Details
Published in:Synlett 2011-04, Vol.2011 (6), p.791-796
Main Authors: Undale, Kedar A., Park, YoonKook, Park, Kyungmoon, Dagade, Dilip H., Pore, Dattaprasad M.
Format: Article
Language:English
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Summary:Abstract A competitive multicomponent synthesis of tetrahydrobenzo[B]pyrans over polyhydroquinolines is achieved in the presence of ammonium acetate at ambient temperature in ethanol medium. The formation of tetrahydrobenzo[B]pyran instead of polyhydroquinoline in solution phase has been confirmed by spectral and single-crystal analysis. The mechanism for the above transformation is suggested and supported by semi-empirical calculations of heat of formation for the intermediates as well as products.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259924