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An easy protocol for the domino synthesis of diversely functionalized spirocarbocycles and their biological evaluation

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Abstract.

A base-catalysed domino reaction for the synthesis of spirocarbocycles in excellent yields using chalcones and vinyl malononitriles is reported. This consists of a series of steps including Knoevenagel condensation followed by intermolecular vinylogous Michael addition and intramolecular cyclization. The synthesized compounds were evaluated for their antimicrobial activity and the compounds exhibited moderate to excellent activities.

Synopsis: A base catalyzed domino reaction for the synthesis of spirocarbocycles in excellent yields using chalcones and vinyl malononitriles is reported. This consists of a series of steps including Knoevenagel condensation followed by intermolecular vinylogous Michael addition and intramolecular cyclization. The synthesized compounds were evaluated for their antimicrobial activity and the compounds exhibited moderate to excellent activities.

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Scheme 1
Scheme 2.
Fig. 1

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Acknowledgments

SEK thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India for the research fellowship. We also thank Department of Chemistry, Indian Institute of Technology, Madras for X-ray single crystal analysis.

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Authors and Affiliations

  1. Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai, 600 020, India

    SELVARANGAM E KIRUTHIKA & PARAMASIVAN T PERUMAL

  2. Division of Microbiology, Entomology Research Institute, Loyola College, Chennai, 600 034, India

    C BALACHANDRAN & S IGNACIMUTHU

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  1. SELVARANGAM E KIRUTHIKA
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  2. PARAMASIVAN T PERUMAL
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  3. C BALACHANDRAN
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Correspondence to PARAMASIVAN T PERUMAL.

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KIRUTHIKA, S.E., PERUMAL, P.T., BALACHANDRAN, C. et al. An easy protocol for the domino synthesis of diversely functionalized spirocarbocycles and their biological evaluation. J Chem Sci 126, 177–185 (2014). https://doi.org/10.1007/s12039-013-0560-1

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