One-pot three-component reaction for facile and efficient green synthesis of chromene pyrimidine-2,4-dione derivatives a
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ORIGINAL PAPER
One‑pot three‑component reaction for facile and efficient green synthesis of chromene pyrimidine‑2,4‑dione derivatives and evaluation of their anti‑bacterial activity Habib Ollah Foroughi1 · Mansoureh Kargar1 · Zahra Erjaee2 · Elham Zarenezhad3 Received: 4 August 2020 / Accepted: 14 September 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract A facile and highly efficient one-pot three-component synthesis of chromene pyrimidine-2,4-dione derivatives from available substrates catalyzed by heteropoly acid (H3PW12O40) is described. In this protocol, the reaction of diverse aldehydes, 4-hydroxycoumarin, and 4-amino-1,3-dimethyluracil in the mixture of EtOH / H2O (1:2) at room temperature in the presence of heteropoly acid (H3PW12O40) as a highly efficient catalyst affords the corresponding chromene pyrimidine-2,4-dione in good to excellent yields. Operational simplicity, low cost, eco-friendly with the environment, easy workup and purification, short reaction time, high yield of products, green media of the reaction and mild conditions are the advantages of this method. The in vitro antibacterial activities of title compounds were obtained against Escherichia coli (ATTC 35218) and Staphylococcus aureus (ATCC 6538) as Gram-negative and Gram-positive bacteria, respectively, and their activities were compared to gentamycin and penicillin as reference drugs. Graphic abstract
Keywords Multicomponent reaction · Heterocycles · Catalysts · Aldehydes
Introduction
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02692-5) contains supplementary material, which is available to authorized users. * Habib Ollah Foroughi [email protected] 1
Department of Science, Fasa Branch, Islamic Azad University, P. O. Box: No. 364, Fasa, Fars 7461713591, Iran
2
Department of Food Science and Technology, Fasa Branch, Islamic Azad University, P. O. Box: No. 364, Fasa, Fars 7461713591, Iran
3
Noncommunicable Diseases Research Center, School of Medicine, Fasa University of Medical Sciences, Fasa, Iran
Phosphotungstic acid is a heteropoly acid (HPA) with the chemical formula H 3PW12O40 is a well-known catalyst and has attracted much attention because of its redox and acidic properties [1]. HPAs have received considerable attention as an inexpensive, eco-friendly catalyst with pseudo liquid behavior, good thermal stability, which is easy to prepare and recyclable. It is widely used as an acid catalyst for different reactions in homogenous liquid media [2]. Design and synthesis of facile and efficient chemical reactions that build up maximum structural diversity and complexity with a minimum number of synthetic steps to provide chemical compounds with interesting properties is a key challenge of modern drug development [3]. Multicomponent
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reactions (MCRs) are regarded as powerful synthetic tools for drug discovery [4]. MCRs are a synthetic methodology in which three or more different starting mater
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