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A consecutive synthesis of spiro[cyclopenta[b]pyrrole-5,2′-indene] derivatives via spirocyclization/annulation reactions

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Abstract

The reaction between ninhydrin-malononitrile adduct [2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)malononitrile] and ethyl 2-(alkylamino)-4-aryl-4-oxo-but-2-enoates (prepared from ethyl 2,4-dioxo-4-arylbutanoate and alkylamines) in the presence of Et3N in MeCN at room temperature afforded 3-alkylamino-2-aryloyl-1′,3′,4-trioxo-1′,3′-dihydrospiro[cyclopentane-1,2′-inden]-2-ene-5,5-dicarbonitriles in 78–95% yields. Five derivatives of these NH-acidic compounds are used to intercept the reactive zwitterionic intermediates generated from dimethyl acetylenedicarboxylate and Ph3P to produce dimethyl 4,4-dicyano-6-aryloyl-1-alkyl-1′,3′-dioxo-1′,2,3′,4-tetrahydro-1H-spiro[cyclopenta[b]pyrrole-5,2′-indene]-2,3-dicarboxylates. Radical scavenging activity of four derivatives was investigated by radical trapping of diphenylpicrylhydrazine and ferric reduction power experiments. The antibacterial activities of six derivatives were studied by disk diffusion test on Gram-positive and Gram-negative bacteria.

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Acknowledgements

We thank the Research Council of Science and Research Branch, Islamic Azad University for supporting this work.

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Authors and Affiliations

  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran

    Azadeh Parhami

  2. Department of Chemistry, Tarbiat Modares University, Tehran, P.O. Box 14115-175, Iran

    Issa Yavari

  3. Department of Chemistry, Qom Branch, Islamic Azad University, Qom, Iran

    Gholam Reza Najafi

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  1. Azadeh Parhami
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Correspondence to Issa Yavari.

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Parhami, A., Yavari, I. & Najafi, G.R. A consecutive synthesis of spiro[cyclopenta[b]pyrrole-5,2′-indene] derivatives via spirocyclization/annulation reactions. Mol Divers 27, 2001–2013 (2023). https://doi.org/10.1007/s11030-022-10535-0

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