PEG-600-Mediated Efficient and Environmentally Sustainable Synthesis of N -[4-(1 H -Benzazole-2-yl)phenyl]phthalimides
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EG-600-Mediated Efficient and Environmentally Sustainable Synthesis of N-[4-(1H-Benzazole-2-yl)phenyl]phthalimides P. Karunakara,b and C. N. S. S. P. Kumarb,* a b
GVK Biosciences Private Limited, IDA Nacharam, Hyderabad, Telangana, 500076 India
Division of Chemistry, Department of Sciences and Humanities, Vignan’s Foundation for Science, Technology & Research (VFSTR) University, Vadlamudi, Andhra Pradesh, 522213 India *e-mail: [email protected] Received July 8, 2019; revised February 10, 2020; accepted February 12, 2020
Abstract—An economically and environmentally sustainable protocol has been proposed for the synthesis of N-[4-(1H-benzazole-2-yl)phenyl]phthalimides via stepwise and tandem reactions of phthalic anhydride, 4-aminobenzaldehyde, and o-phenylenediamine, N-methyl-o-phenylenediamine, 2-aminobenzenethiol, or 2-aminophenol in PEG-600 for 2–3 h in the presence of boric acid as catalyst. Binding of the synthesized molecules to the tubulin protein (PDB ID: 5CA1) was simulated using AutoDock. All molecules showed good binding energies as compared to Nocodazole. This simple methodology could be useful for environmentally sustainable chemistry with the advantages including shorter reaction time, nontoxic and nonhazardous catalyst, and mild conditions. Keywords: PEG-600, phthalic anhydride, boric acid, environmentally sustainable synthesis
DOI: 10.1134/S1070428020070246 INTRODUCTION The development of efficient, economical, and environmentally sustainable synthesis is of great importance for modern organic synthesis [1]. In many synthetic organic processes organic solvents represent the highest pollution problem. Therefore, replacement of hazardous solvents by relatively green solvents or elimination of solvents from chemical processes has been one of the key areas of green chemistry [2]. Based on the green chemistry principles, a green solvent should meet numerous criteria such as low toxicity, non-volatility, non-mutagenicity, non-flammability, and widespread availability among others [3]. In the past decade, water [4], glycerol [5], polyethylene glycol [6], and ionic liquids [7] have been shown as the most important options for current solvent innovation. Nowadays, PEG-600 has attracted much interest in the context of environmentally sustainable synthesis. Indeed, PEG-600 was considered an attractive green solvent for various organic reactions [8]. The choice of PEG-600 was provoked by several factors like its nonvolatility, thermal stability, and commercial availability [9]. Additionally, PEG-600 is a reasonably priced, fully non-halogenated, and easily degradable solvent that possesses low toxicity [10]. PEG-600 has been used as
a complexing solvent with unique properties of cationic coordination ability [11]. Phthalic anhydride is used in the manufacture of dialkyl phthalates [12] which find application as plasticisers for polymers like polyvinyl chloride (PVC), polyvinyl acetate (PVA), etc. It is used in the manufacture of phenolphthalein indicator [13], anthraquinone [14] (a versatile raw ma
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