10.57647/j.ijc.2025.1501.06

Bicyclic 1,2,3-Triazolium Ionic Liquids as a novel ionic liquid based catalytic systems for the preparation of spirobenzo[f]pyrano[3,2-c]chromene derivatives under ultrasonic irradiation conditions

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  • Abbas Fazlinia1,
  • Fatemeh Hosna Tavakoli2,
  • Majid Ghashang*2,
  1. Department of Chemistry, Zarghan Branch, Islamic Azad University, Zarghan, Iran
  2. Department of Chemistry, Najafabad Branch, Islamic Azad University, Najafabad, Iran
Bicyclic 1,2,3-Triazolium Ionic Liquids as a novel ionic liquid based catalytic systems for the preparation of spirobenzo[f]pyrano[3,2-c]chromene derivatives under ultrasonic irradiation conditions

Received: 2024-01-30

Revised: 2024-05-11

Accepted: 2024-11-21

Published 2024-11-25

Copyright (c) 2024 Abbas Fazlinia, Fatemeh Hosna Tavakoli, Majid Ghashang (Author)

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This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

Fazlinia, A., Tavakoli, F. H., & Ghashang, M. (2024). Bicyclic 1,2,3-Triazolium Ionic Liquids as a novel ionic liquid based catalytic systems for the preparation of spirobenzo[f]pyrano[3,2-c]chromene derivatives under ultrasonic irradiation conditions. Iranian Journal of Catalysis, 15(1 (March 2025), 1-8. https://doi.org/10.57647/j.ijc.2025.1501.06
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Abstract

A novel ionic liquid, 2-butyl-4,5,6,7-tetrahydro-2H-[1,2,3]triazolo[1,5-a]pyridin-8-ium hydrogen sulfate, was synthesized and employed as an efficient catalyst in the high-yield synthesis of spiro compounds featuring the benzo[f]pyrano[3,2-c]chromene scaffold. Through a three-component reaction involving 1-hydroxy-3H-benzo[f]chromen-3-one, malononitrile, and 1-benzylindoline-2,3-dione in ethanol under reflux and ultrasonic irradiation, 10 distinct compounds were successfully obtained in excellent yields ranging from 86% to 97%. The products were characterized comprehensively by Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), and CHN analysis. Notably, the protocol offers an efficient, non-chromatographic method for separation and purification, ensuring high-yield productivity and operational simplicity, making it a highly advantageous approach for synthesizing spiro compounds.

Research Highlights

  • Bicyclic 1,2,3-Triazolium Ionic Liquids were prepared and used for the preparation of some spiro compounds.
  • Spiro compounds with the benzo[f]pyrano[3,2-c]chromene moiety were prepared by a three-component reaction.
  • The nonchromatographic separation and purification of the products with high-yield productivity are the salient features of this protocol.
  • All reactions proceed well and the products were formed in high yields.

Keywords

  • Benzo[f]pyrano[3,2-c]chromene,
  • Catalyst,
  • Ionic liquid,
  • 1-hydroxy-3H-benzo[f]chromen-3-one,
  • Spiro compounds
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