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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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.
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container_issue 6
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container_title Synlett
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creator Undale, Kedar A.
Park, YoonKook
Park, Kyungmoon
Dagade, Dilip H.
Pore, Dattaprasad M.
description 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.
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title A Revisit to the Hantzsch Reaction: Unexpected Formation of Tetrahydro­benzo[b]pyrans beyond Polyhydroquinolines
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