6-(TRIFLUOROMETHYL)-2H-PYRAN-2-ONES: PROMISING CF3-BEARING CONJUGATED CYCLIC DIENE AND ELECTROPHILIC BUILDING-BLOCKS

Abstract

This review describes synthetic methods for the preparation of such advanced conjugated cyclic dienes and electrophiles as 6-CF3-2-pyrones (6-(trifluoromethyl)-2H-pyran-2-ones), their versatile chemical properties and use in the syntheses of various CF3-containing cycloadducts, highly functionalized trifluoromethylated aromatic and heteroaromatic compounds. Synthesis of 6-CF3-2-pyrones bearing a substituent (substituents) at position(s) 3, 4 and 5, regio- and stereoselective preparation of trifluoromethylated cycloadducts (and their derivatives) via Diels?Alder reactions (and retro hetero?Diels?Alder reaction) from these pyrones and compounds containing in their molecules a reactive double (triple) bond, as well as reactions with nucleophiles has been presented in the review. Due to the presence of the electron-withdrawing trifluoromethyl group and the diene moiety, 6-CF3-2-pyrones are highly reactive substrates towards both dienophiles and nucleophiles. High regio- and stereoselectivity of the reactions allows the use of these excellent CF3-containing building-blocks for the preparation of various bicyclic, aromatic and heteroaromatic compounds, important starting substrates in biological or medicinal chemistry and related areas.

Keywords

Trifluoromethyl, fluoroalkyl pyronesDiels?Alder reactionTrifluoromethylated bicyclic compoundsTrifluoromethylated aromatic compoundsTrifluoromethylated heterocycles

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