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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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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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  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Davood Habibi, Atefeh Shamsian & Davood Nematollahi

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  1. Davood Habibi
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  2. Atefeh Shamsian
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  3. Davood Nematollahi
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Correspondence to Davood Habibi.

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Habibi, D., Shamsian, A. & Nematollahi, D. Synthesis of pyranopyrazoles, benzopyrans, amino-2-chromenes and dihydropyrano[c]chromenes using ionic liquid with dual Brønsted acidic and Lewis basic sites. Chem. Pap. 69, 586–595 (2015). https://doi.org/10.1515/chempap-2015-0066

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