Revisit to the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives in lactic acid media as a green solvent and cat
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ORIGINAL ARTICLE
Revisit to the synthesis of 1,2,3,4‑tetrasubstituted pyrrole derivatives in lactic acid media as a green solvent and catalyst Dilek Akbaslar1 · E. Sultan Giray1 · Oztekin Algul2 Received: 12 May 2020 / Accepted: 30 June 2020 © Springer Nature Switzerland AG 2020
Abstract In this study, for the first time, lactic acid was used as a bio-based green catalyst and reaction medium for the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives from one-pot three-component reaction of commercially available primary amines, 1,3-dicarbonyl compounds, and trans-β-nitrostyrene at room temperature. Thirty-three corresponding pyrroles, of which eight are novel and have been reported for the first time, were synthesized in high to excellent yields in lactic acid media and characterized by spectroscopic analysis. In all examined cases, lactic acid represented many advantages, including shorter reaction time, ease of product isolation, higher yields, no by-products, no chromatographic process, and lower volatility in the reaction. This bio-based green solvent can also be recycled and reused three times without loss of its efficiency as a catalyst and solvent. Graphic abstract
Keywords Lactic acid · Tetrasubstituted pyrroles · Green synthesis · Multicomponent reaction
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-020-10122-1) contains supplementary material, which is available to authorized users. * E. Sultan Giray [email protected] * Oztekin Algul [email protected] 1
Department of Chemistry, Art and Science Faculty, Cukurova University, Adana, Turkey
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin, Turkey
2
Pyrrole and its derivatives are one of the most relevant nitrogen-containing heterocyclic compounds that are found not only in a broad range of natural products, such as heme, cytochromes, vitamin B12, and alkaloids [1, 2], but also in agrochemicals and pharmaceuticals [3]. They are also identified as an important scaffold in biologically active compounds, such as lamellarins [4, 5], lukianols [6], and ningalin B [7, 8] (Fig. 1). These compounds are used as key synthetic intermediates of serotonin antagonists [9], tumor necrosis factor antagonists [10], cyclin-dependent
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Molecular Diversity
Fig. 1 Representatives of biologically active natural pyrrole products
kinase inhibitors [11, 12], and cytosolic phospholipase A2 inhibitors [13]. Pyrrole and its derivatives are also present in several drugs, including atorvastatin [14], tolmetin [15], ketorolac [16], licofelone [17], and sunitinib [18] (Fig. 2). Furthermore, pyrroles are known to show notable biological activities, such as antitumor [19], anti-HIV [20], antibacterial [21], antifungal [22], antimalarial [23], antioxidant [24], ionotropic [25], and antiinflammatory [26]. Due to their biological importance, significant efforts have been made to develop novel and efficient methods to produce fun
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