ChemInform Abstract: Approaches to the Synthesis of Anthracyclinones and Heteroanthracyclinones: Synthesis of Benzoyl‐1,4‐benzoquinones, Their Diels‐Alder Reactions and (1,5)‐Rearrangement of Adducts

Abstract

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Recent advances in 1,4-benzoquinone chemistry

“…Tsutui et al 218 performed theoretical calculations on silyl-substituted 1,4-benzoquinones (190)(191)(192)(193)(194)(195)(196)(197), to investigate the structure and properties. Geometry optimizations and vibrational frequency calculations were performed at B3LYP/6-31G* level while the SPE calculation is carried out at MP2/6-311+G(2d,p) level.…”

“…Multi-step synthesis of heteroacyl-and aroyl-1,4-benzoquinones by Pardasani and co-workers. [197][198][199][200] varieties of substituted quinones. Applying this multi-step strategy, we could successfully synthesize differently substituted benzoyl-1,4-benzo-quinones, [196][197][198] furanoyl/ thienoyl-1,4-benzoquinones 199 and thiophenacetoyl-1,4-benzoquinones.…”

“…Similar Diels-Alder reactions of numerous 1,4-benzoquinones have been subsequently reported by our group. 198,326,327 Chen et al 328 achieved a typical cycloaddition reaction of zirconacyclopentadiene (224) to various quinones leading to a 6-membered adduct (Scheme 67). Kang et al 320 This is an efficient method for higher quinones by a zirconium/CuCl mediated cycloaddition reactions of two alkynes and quinone in a one-pot procedure.…”