320750-27-4Relevant articles and documents
3-(2-benzoylallyl)-4-hydroxy-6-methylpyran-2-ones: Synthesis and intra- and intermolecular nucleophilic additions
Girreser, Ulrich,Heber, Dieter,Schütt, Martin
, p. 2421 - 2436 (2007/10/03)
The reaction of 4-hydroxy-6-methylpyran-2-one (6) with 1-aryl-2-(dimethylaminomethyl)prop-2-en-1-ones (2) is investigated systematically in order to assess its suitability in carbon-carbon bond forming reactions as well as to provide the conditions for subsequent ring closure. Using a base-free medium the reaction affords the title 3-(2-benzoylallyl)-4-hydroxy-6-methylpyran-2-ones (7), whereas in the presence of triethylamine the pyrano[4,3-b]pyranes (8) are formed directly. This result is not necessarily contradictory to the Baldwin rules for ring closure. The structures and the mechanism defined is supported by IR and NMR spectroscopy. The intermolecular addition of further nucleophiles to the enone double bond of 7 yields miscellaneous 3-substituted 2-pyrones (14).