Issue 50, 2016, Issue in Progress

DABCO-based ionic liquids: green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media

Abstract

A new and straightforward method for the synthesis of 5-arylidine barbituric and thiobarbituric acids through a reaction between barbituric acid and its thio-analogue with aldehydes using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate ([DABCO](SO3H)2(HSO4)2) as an efficient catalyst has been reported. In this project, also the preparation of pyrano[2,3-d]-pyrimidinediones via the reaction of barbituric or thiobarbituric acid, malononitrile and aldehydes in the presence of this reagent and 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium chloride ([DABCO](SO3H)2(Cl)2) has been investigated. The structure of the products was characterized using IR, 1H NMR and 13C NMR spectroscopy. The present methodologies suggests several advantages such as ease of the preparation and handling of the catalysts, high yields, simple and green procedures, low cost, short reaction times, easy work-up and preformation of the reaction in water as a green solvent.

Graphical abstract: DABCO-based ionic liquids: green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media

Supplementary files

Article information

Article type
Paper
Submitted
05 Mar 2016
Accepted
28 Apr 2016
First published
05 May 2016

RSC Adv., 2016,6, 44630-44640

DABCO-based ionic liquids: green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media

N. Seyyedi, F. Shirini and M. S. Nikoo Langarudi, RSC Adv., 2016, 6, 44630 DOI: 10.1039/C6RA05878G

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