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Design of novel 2-amino-pyrans via a green and facile one-pot multicomponent protocol using RuO2/Al2O3 as reusable catalyst

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Abstract

A facile, eco-friendly, and efficient approach for the multicomponent synthesis of 2-amino-pyran analogues (4a–j) is described that involves the reaction of substituted aldehydes, methyl cyanoacetate, and 1,3-cyclohexadione in a one-pot method using ruthenia-doped alumina (RuO2/Al2O3) as heterogeneous catalyst in a green solvent system. A simple wet-impregnation approach was used to prepare the catalyst material and was well-characterized using several analytical techniques like PXRD, TEM, SEM, SEM–EDX, and BET analysis. The key benefits of the current protocol are operational simplicity, economy, green reaction conditions, easy workup, short reaction time (10 min), higher product yields (94–98%), and no need for column chromatographic purification. The additional key advantage of this method is the recyclability and reusability of catalyst material up to eight runs through simple filtration without any significant loss of its catalytic activity.

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Acknowledgements

The authors are very thankful to the Andhra University, and GITAM Deemed to be University, Visakhapatnam, India, for instrumentation, research, and financial support.

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This work received no fund from any source.

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Authors and Affiliations

  1. Department of Chemistry, GITAM Institute of Sciences, GITAM University, Visakhapatnam, Andhra Pradesh, 530045, India

    Buri Apparao, Alice R. Robert, Pamerla Muralidhar & Suresh Maddila

  2. College of Pharmaceutical Sciences, Andhra University, Visakhapatnam, Andhra Pradesh, 530003, India

    Muthyala Murali Krishna Kumar

  3. Department of Physics, School of Sciences, Woxsen University, Hyderabad, Telangana, 502345, India

    Rama Krishna Madaka

  4. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills , Durban, 4000, South Africa

    Suresh Maddila & Sreekantha B. Jonnalagadda

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  1. Buri Apparao
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  2. Alice R. Robert
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  3. Muthyala Murali Krishna Kumar
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  4. Rama Krishna Madaka
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Contributions

BA performed experimental studies and conceptualization; ARR performed writing—original draft and conceptualization; MMKK provided facilities for the spectral characterization; RM provided facilities for the catalyst characterization; PM performed validation, data curation, and formal analysis; SM: performed conceptualization, project administration, writing—original draft, supervision and funding acquisition; SBJ performed review and editing.

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Correspondence to Suresh Maddila.

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Apparao, B., Robert, A.R., Kumar, M.M.K. et al. Design of novel 2-amino-pyrans via a green and facile one-pot multicomponent protocol using RuO2/Al2O3 as reusable catalyst. Res Chem Intermed 49, 1043–1058 (2023). https://doi.org/10.1007/s11164-022-04949-6

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