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Microwave-assisted conditions have been shown to be very efficient for the synthesis of a variety of compounds containing 2 H-pyran-2-one skeleton that plays important roles in nature and in synthetic chemistry. Furthermore, such compounds (especially those incorporating a 3- acylamino group) were shown to be efficient partners for the Diels-Alder reactions with a variety of dienophiles including acetylene derivatives, maleic anhydride, substituted maleimides, vinyl-moiety-containing dienophiles, as well as ( Z)-1-methoxybut-1-en-3-yne. Reactions were carried out under conventional thermal conditions, microwave irradiation and under high pressure (13-15 kbar) and resulted in a plethora of different product types: anilines, bi- and terphenyls, indoles, isoindoles, 2-oxabicyclo (2.2.2 )oct-5-enes and bicyclo (2.2.2 )octenes. Many of the transformations showed remarkable regio- and stereoselectivity, depending primarily on the substitution patterns of the reactants and reaction conditions applied.

Regio- and stereoselective syntheses and cycloadditions of substituted 2H-pyran-2-ones and their fused derivatives