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1-(4-Sulfonic Acid Butyl)-3-Methylimidazolium Polyoxo Metalate as a Novel Nano-Hybrid Catalyst for the One-Pot Synthesis of 4H-Pyran and Spiro Indoline Derivatives.

Authors :
Hojati, Seyedeh Fatemeh
Moeini-Eghbali, Nasrin
Mohammadi, Sara
Jamshidi, Ali
Mohammadi Zonoz, Farokhzad
Maleki, Behrooz
Source :
Polycyclic Aromatic Compounds; 2023, Vol. 43 Issue 9, p8282-8306, 25p
Publication Year :
2023

Abstract

Organic-inorganic nanohybrid ionic liquid based on polyoxometalate [H<subscript>2</subscript> [MIMBS]<subscript>4</subscript> [P<subscript>2</subscript>W<subscript>18</subscript>O<subscript>62</subscript>].11H<subscript>2</subscript>O] (MIMB-P<subscript>2</subscript>W<subscript>18</subscript>) has been synthesized and characterized by elemental analysis technique, Fourier transform infrared (FT-IR), <superscript>1</superscript>H, <superscript>13</superscript>C, and <superscript>15</superscript>P nuclear magnetic resonance (NMR), powder X-ray diffraction (XRD), thermogravimetric analysis (TGA) and scanning electron microscopy (SEM). The catalytic activity of this nanohybrid ionic liquid has been studied in multi-component reactions to generate pyran and spiro indoline derivatives. Tetrahydrobenzo[b]pyrans have been successfully synthesized by one-pot three-component condensation of aldehyde, malononitrile and dimedone (or cyclohexane-1,3-dione/3-methyl-2-pyrazoline-5-one) using MIMB-P<subscript>2</subscript>W<subscript>18</subscript> as a heterogeneous nano-catalyst. Furthermore, a set of multi-substituted spiro[indoline-3,4׳-pyrano[2,3-c]pyrazole] has been synthesized from isatin, hydrazinehydrate/phenylhydrazine, ethyl acetoacetate and malononitrile/ethyl cyanoacetate in the presence of the same catalyst via one-pot four-component method at room temperature. These procedures have several advantages such as high yields of product, easy work-up procedure, short reaction time and stability, non-toxicity, cheapness and reusability of the catalyst. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
10406638
Volume :
43
Issue :
9
Database :
Complementary Index
Journal :
Polycyclic Aromatic Compounds
Publication Type :
Academic Journal
Accession number :
173321540
Full Text :
https://doi.org/10.1080/10406638.2022.2149562