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Synlett 2011(6): 791-796  
DOI: 10.1055/s-0030-1259924
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Kedar A. Undalea, YoonKook Parkb, Kyungmoon Parkb, Dilip H. Dagadea, Dattaprasad M. Pore*a,b
a Department of Chemistry, Shivaji University, Kolhapur- 416004, India
b Department of Biological and Chemical Engineering, Hongik University, Jochiwon, Chungnam-339-701, Korea
Fax: +91(231)2692333; e-Mail: p_dattaprasad@rediffmail.com;
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Publication History

Received 15 December 2010
Publication Date:
16 March 2011 (online)

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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.

Key words

multicomponent synthesis - tetrahydrobenzo[b]pyrans - ammonium acetate - semi-emperical calculations

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