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Construction of Dispiro-Indenone Scaffolds via Domino Cycloaddition Reactions of ?,?-Unsaturated Aldimines with 2-Arylidene-1,3-indenediones and 2,2'-(Arylmethylene)bis(1,3-indenediones).

ABSTRACT: The catalyst-free domino reaction of ?,?-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 ?,?-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.

SUBMITTER: Yang WJ

PROVIDER: S-EPMC6705284 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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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).

Yang Wen-Juan WJ Fang Hui-Lin HL Sun Jing J Yan Chao-Guo CG

ACS omega 20190807 8

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 ...[more]

PMID: 31460485

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