Cyclization vs. Elimination Reactions of 5-Aryl-5-hydroxy 1,3-Diones: One-Pot Synthesis of 2-Aryl-2,3-dihydro-4H-pyran-4-ones

[摘要]：2-Aryl-2,3-dihydro-4H-pyran-4-ones were prepared in one step by cyclocondensation of 1,3-diketone dianions with aldehydes. The use of HCl (10%) for the aqueous workup proved to be very important to avoid elimination reactions of the 5-aryl-5-hydroxy 1,3-diones formed as intermediates. The TiCl4-mediated cyclization of a 2-aryl-2,3-dihydro-4H-pyran-4-one with 1,3-silyloxybuta-1,3-diene resulted in cleavage of the pyranone moiety and formation of a highly functionalized benzene derivative.

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