Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions

Atefeh Saadat  -  Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran, Islamic Republic of
*Abdolkarim Zare  -  Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran, Islamic Republic of
Fatemeh Jamadi  -  Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran, Islamic Republic of
Maasoomeh Abdolalipour-Saretoli  -  Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran, Islamic Republic of
Received: 21 Jun 2017; Revised: 6 Oct 2017; Accepted: 9 Oct 2017; Published: 1 Aug 2018; Available online: 11 Jun 2018.
Open Access Copyright (c) 2018 Bulletin of Chemical Reaction Engineering & Catalysis
License URL: http://creativecommons.org/licenses/by-sa/4.0

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Abstract

In this work, a novel Brønsted acidic ionic liquid namely triethylaminium-N-sulfonic acid trifluoroacetate {[TEASA][TFA]} has been synthesized by the reaction of NEt3 with ClSO3H, and then with CF3CO2H. The ionic liquid has been characterized by studying its spectroscopic data (1H and 13C NMR, FT-IR, and mass spectra). Afterward, it has been utilized as a highly effective and general catalyst to promote the following organic reactions in solvent-free conditions: (i) the production of 1-thioamidoalkyl-2-naphthols from arylaldehydes, 2-naphthol and thioacetamide, and (ii) the preparation of 14-aryl-14H-dibenzo[a,j]xanthenes from arylaldehydes and 2-naphthol. It is noteworthy that [TEASA][TFA] has catalyzed the reactions under milder conditions relative to most of the reported methods. Moreover, it afforded the both products in higher yields with respect to most of the previous works. Copyright © 2018 BCREC Group. All rights reserved

Received: 21st June 2017; Revised: 6th October 2017; Accepted: 9th October 2017; Available online:  11st June 2018; Published regularly: 1st August 2018

How to Cite: Saadat, A., Zare, A., Jamadi, F., Abdolalipour-Saretoli, M. (2018). Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions. Bulletin of Chemical Reaction Engineering & Catalysis, 13 (2): 204-212 (doi:10.9767/bcrec.13.2.1280.204-212)

 

Keywords: Triethylaminium-N-sulfonic acid trifluoroacetate {[TEASA][TFA]}; Brønsted acidic ionic liquid; 1-Thioamidoalkyl-2-naphthol; 14-Aryl-14H-dibenzo[a,j]xanthene
Funding: Research Council of Payame Noor University

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