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Issue 16, 2019
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Selective synthesis of spirooxindoles via a two-step reaction of N-phenacylpyridinium bromide, 1,3-indanedione and N-alkylisations

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Abstract

The three-component reaction of 1,3-indanedione and N-alkylisatins with two molecular N-phenacylpyridinium salts in dry acetonitrile in the presence of triethylamine resulted in unique functionalized spiro[indoline-3,4′-naphtho[1,2-b]furan] derivatives in good yields, which were successfully converted to spiro[indoline-3,2′-naphthalen]-4′-yl acetate derivatives by acylation with acetyl chloride in methylene dichloride and alkoxy-substituted spiro[benzo[h]chromene-5,3′-indolines] by acid-catalyzed etherification reaction in alcohol. The reaction mechanism involved the sequential cycloaddition of the in situ-generated pyridinium ylide to dipolarophilic enone, ring-opening of 1,3-indanedione, and selective annulation.

Graphical abstract: Selective synthesis of spirooxindoles via a two-step reaction of N-phenacylpyridinium bromide, 1,3-indanedione and N-alkylisations

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Publication details

The article was received on 22 Jan 2019, accepted on 27 Mar 2019 and first published on 28 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00166B
Citation: Org. Biomol. Chem., 2019,17, 3978-3983

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    Selective synthesis of spirooxindoles via a two-step reaction of N-phenacylpyridinium bromide, 1,3-indanedione and N-alkylisations

    J. Sun, Y. Zhang, R. Shi and C. Yan, Org. Biomol. Chem., 2019, 17, 3978
    DOI: 10.1039/C9OB00166B

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