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Expeditious reaction of ninhydrin with active methylene compounds on montmorillonite K10 clay

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Abstract

Ninhydrin reacted expeditiously with thirteen active methylene compounds on montmorillonite K10 clay at room temperature to furnish, in 5 min, a Knoevenagel condensate in one case, aldols in six cases, aldol-derived cyclic hemiketals in three cases, and interesting products in the remaining three cases. Almost identical results were obtained, but faster, when the reactions were carried out in water on steam-bath. The structures of two novel products were also confirmed by single-crystal X-ray diffraction analysis.

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Acknowledgments

We sincerely thank Professor S. Raha, Director, Bose Institute, for laboratory facilities, the C.S.I.R., Govt. of India for providing a fellowship (A.M.), Mr B. Majumder, NMR facilities, and Mr P. Dey, Microanalytical Laboratory, both of the Bose Institute, for recording the spectra.

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Authors and Affiliations

  1. Department of Chemistry, Bose Institute, 93/1, A. P. C. Road, Kolkata, 700009, India

    Manas Chakrabarty & Ajanta Mukherji

  2. School of Pharmaceutical Sciences, Kitasato University, Minato-ku, Tokyo, 108, Japan

    Shiho Arima & Yoshihiro Harigaya

  3. Laboratoire des Multi-matériaux et Interfaces, Groupe de Cristallographie et Ingénierie Moléculaire, UMB 5615 CNRS–Université Claude Bernard, Lyon 1, France

    Guillaume Pilet

Authors
  1. Manas Chakrabarty
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  2. Ajanta Mukherji
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  3. Shiho Arima
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  4. Yoshihiro Harigaya
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  5. Guillaume Pilet
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Correspondence to Manas Chakrabarty.

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Chakrabarty, M., Mukherji, A., Arima, S. et al. Expeditious reaction of ninhydrin with active methylene compounds on montmorillonite K10 clay. Monatsh Chem 140, 189–197 (2009). https://doi.org/10.1007/s00706-008-0066-6

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  • DOI: https://doi.org/10.1007/s00706-008-0066-6

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