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26.4 Product Class 4: 1,2-Diketones and Related Compounds

DOI: 10.1055/sos-SD-026-00532

Landais, Y.; Vincent, J. M.Science of Synthesis, (200526647.

General Introduction

The synthesis and reactivity of 1,2-diketones (α-diketones) have been studied extensively and reviewed.[‌1‌,‌2‌] 1,2-Diketones 1 are dielectrophilic compounds whose reactivity at one carbonyl moiety is enhanced by the presence of the second carbonyl group. Thus 1,2-diketones readily react with nucleophiles such as amines, alcohols, thiols, and carbanions.[‌1‌,‌3‌] Reaction at both carbonyl groups has also been used to prepare heterocycles. Cyclocondensation of 1,2-dicarbonyl compounds with aromatic o-diamines gives quinoxalines, which have useful pharmacological activities. Extension of this condensation to bis-1,2-dicarbonyl compounds and bis-o-diamines also leads to an important class of polymers, i.e. the polyquinoxalines.[‌1‌] 1,2-Diketones have been used in a [3+2]-annulation strategy in which they react efficiently with dianion equivalents such as bis(silyl enol ethers) or 3-halo-2-(silylmethyl)propenes to produce the corresponding cyclopentane skeletons such those found in 2 and 3 (Scheme 1).[‌4‌,‌5‌]

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