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

Kedar A. Undale; YoonKook Park; Kyungmoon Park; Dilip H. Dagade; Dattaprasad M. Pore

doi:10.1055/s-0030-1259924

LETTER

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

Kedar A. Undale^a, YoonKook Park^b, Kyungmoon Park^b, Dilip H. Dagade^a, 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;

Abstract

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

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