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Construction of Dispiro-Indenone Scaffolds via Domino Cycloaddition Reactions of α,β-Unsaturated Aldimines with 2‑Arylidene-1,3-indenediones and 2,2′-(Arylmethylene)bis(1,3-indenediones)

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journal contribution
posted on 07.08.2019, 12:40 authored by Wen-Juan Yang, Hui-Lin Fang, Jing Sun, Chao-Guo Yan
The catalyst-free domino reaction of α,β-unsaturated N-alkyl or N-arylaldimines with two molecules of 2-arylidene-1,3-indanediones in dry acetonitrile resulted in polysubstituted spiro­[indene-2,3′-indeno­[2′,1′:5,6]­pyrano­[2,3-b]­pyridines] in moderate to good yields and with high diastereoselectivity. The reaction mechanism included sequential aza/oxa-Diels–Alder reactions via both endo-transition states. On the other hand, the catalyst-free domino reaction of α,β-unsaturated N-arylaldimines with 2,2′-(arylmethylene)­bis­(1,3-indenediones) afforded the mixed diastereoisomeric dispiro­[indene-2,1′-cyclohexane-3′,2″-indene] derivatives in satisfactory yields. The reaction mechanism of this formal [3 + 3] cycloaddition was believed to proceed with sequential nucleophilic 1,4-/1,2-additions.