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A Revisit to the Hantzsch Reaction: Unexpected Formation of Tetrahydrobenzo[b]pyrans beyond Polyhydroquinolines
- Issue Date
- 1-Apr-2011
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- multicomponent synthesis; tetrahydrobenzo[b]pyrans; ammonium acetate; semi-emperical calculations
- Citation
- SYNLETT, no.6, pp.791 - 796
- Journal Title
- SYNLETT
- Number
- 6
- Start Page
- 791
- End Page
- 796
- ISSN
- 0936-5214
- 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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Related Researcher
- Park, YoonKook
- Science & Technology (Biological and Chemical Engineering)