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Amine Functionalized Dendronized Polymer as a Homogeneous Base Catalyst for the Synthesis of Polyhydroquinolines and 4-Arylidene-3-Methylisoxazol-5(4H)-Ones

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Abstract

Novel isosorbide initiated polyepichlorohydrin cored PPI dendronized polymer (ISO-PECH-Amine-G1) has been prepared and its structure was determined by different spectro- analytical techniques. The catalytic activity of ISO-PECH-Amine-G1 was explored for the synthesis of polyhydroquinolines and 4-arylidene-3-methylisoxazol-5(4H)-ones. From an eco-benign perspective, the notable advantages of this protocol are as follows: (i) water as reaction medium, (ii) transition metal-free, (iii) no toxic by-products, (iv) room temperature reaction, (v) simple experimental and work-up procedure, (vi) high conversion, (vii) shorter reaction time, (viii) diverse substrate scope, (ix) no need of solvent extraction and (x) facile reusability of the catalyst. In addition, computational calculations were performed using the B3LYP/6-31G level of theory to explore various density functional theory (DFT) based descriptors such as dipole moment, hardness, chemical potential, electrophilicity index, and the nucleophilicity index of the synthesized derivatives.

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Acknowledgements

H. K. gratefully acknowledges financial support in the form of a Senior Research Fellowship from the University Grants Commission (UGC), New Delhi, India, and India SAP UGC.

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  1. Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, 682022, India

    K. Hiba, S. Prathapan & K. Sreekumar

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  1. K. Hiba
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  2. S. Prathapan
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  3. K. Sreekumar
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Correspondence to K. Sreekumar.

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10562_2021_3829_MOESM1_ESM.docx

Supplementary file1 Experimental procedure for the synthesis of the catalyst ISO-PECH-Amine-G1, polyhydroquinoline scaffolds, and 4-arylidene-3-methylisoxazol-5(4H)-ones. Structure, analytical data, GC/MS, 1H NMR and 13C NMR of synthesized polyhydroquinolines and 4-arylidene-3-methylisoxazol-5(4H)-ones (DOCX 2894 kb)

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Hiba, K., Prathapan, S. & Sreekumar, K. Amine Functionalized Dendronized Polymer as a Homogeneous Base Catalyst for the Synthesis of Polyhydroquinolines and 4-Arylidene-3-Methylisoxazol-5(4H)-Ones. Catal Lett 152, 2457–2469 (2022). https://doi.org/10.1007/s10562-021-03829-9

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