Synthesis of pyranopyrazoles, benzopyrans, amino-2-chromenes and dihydropyrano[c]chromenes using ionic liquid with dual Brønsted acidic and Lewis basic sites
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Davood Habibi
,
Atefeh Shamsian
Abstract
An efficient ionic liquid with both Brønsted acidic and Lewis basic sites, namely 1,4-dimethyl-1- (4-sulphobutyl)piperazinium hydrogen sulphate (IL1), was synthesised and characterised. IL1 is a “green”, homogeneous and reusable catalyst for: i) the synthesis of pyranopyrazoles (Va-Vj) and benzopyrans (VIa-VIj and VIIa-VIIf) at ambient temperature under solvent-free conditions and ii) the synthesis of amino-2-chromenes (VIIIa-VIIIi and IXa-IXi) and dihyropyrano[c]chromenes (Xa- Xi) at 80◦C under solvent-free conditions. The reactions were rapid with excellent product yields. In addition, the double Brønsted acid, 1,4-dimethyl-1,4-bis(4-sulphobutyl)piperazinium hydrogen sulphate (IL2), was prepared to evaluate the cooperation efficiency of their Brønsted acidic and Lewis basic sites as compared with the double Brønsted acidic sites in IL1
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© 2015 Institute of Chemistry, Slovak Academy of Sciences
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