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Sodium Dodecyl Sulphate Catalyzed One-Pot Three-Component Synthesis of Structurally Diverse 2-Amino-3-cyano Substituted Tetrahydrobenzo[b]pyrans and Spiropyrans in Water at Room Temperature

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Abstract

A facile and convenient method has been developed for the one-pot three-component synthesis of 2-amino-3-cyano substituted tetrahydrobenzo[b]pyran derivatives from the reactions of aromatic aldehydes, malononitrile and dimedone or 1,3-cyclohexanedione in the presence of a catalytic amount of sodium dodecyl sulphate as an efficient surfactant type catalyst in water at room temperature. Synthesis of 2-amino-3-cyano substituted spiropyrans was also achieved under the same reaction conditions starting from ninhydrin/isatins, malononitrile and dimedone or 1,3-cyclohexanedione. All the reactions were completed within 2.5 h and the desired products afforded in good to excellent yields. Gram scale production of the desired compound was also achieved. Use of water as green solvent, commercially available low cost surfactant type catalyst, high atom economy, excellent yields, energy efficiency, no column chromatographic purifications, reusability of the solvent media, multiple carbon–carbon and carbon-heteroatom bond formations are some of the major advantages of this newly developed protocol.

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Acknowledgements

Dr. B. Banerjee is thankful to the Akal University, Talwandi Sabo, Punjab, India and the Kalgidhar Trust, Baru Sahib, Himachal Pradesh, India for the support. Authors are grateful to AMRC, IIT Mandi, Himachal Pradesh, India for the spectral measurements such as FT-IR, 1H and 13C NMR, HRMS and single X-ray crystal data.

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Authors and Affiliations

  1. Department of Chemistry, Akal University, Talwandi Sabo, Bathinda, Punjab, 151302, India

    Bubun Banerjee, Anu Priya, Manmeet Kaur, Aditi Sharma & Arvind Singh

  2. Visiting Researcher, Eternal University, Baru Sahib, Himachal Pradesh, 173101, India

    Bubun Banerjee

  3. Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, Jammu, 180 006, India

    Vivek Kumar Gupta

  4. Department of Pharmaceutical Sciences and Natural Products School of Health Sciences, Central University of Punjab, Bathinda, Punjab, 151401, India

    Vikas Jaitak

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In the memory of our heavenly colleague, Dr. Arvinder Singh, Associate Professor, Department of Botany, Akal University, Talwandi Sabo, Bathinda.

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Banerjee, B., Priya, A., Kaur, M. et al. Sodium Dodecyl Sulphate Catalyzed One-Pot Three-Component Synthesis of Structurally Diverse 2-Amino-3-cyano Substituted Tetrahydrobenzo[b]pyrans and Spiropyrans in Water at Room Temperature. Catal Lett 153, 3547–3560 (2023). https://doi.org/10.1007/s10562-022-04256-0

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