Succinimidium perchlorate as a novel and efficient Brönsted acidic ionic liquid promoter for the synthesis of 5-arylidene barbituric acid and pyrano[2,3-d] pyrimidinone derivatives

IF 0.9 Q4 CHEMISTRY, PHYSICAL

Current Organocatalysis Pub Date : 2023-04-20 DOI:10.2174/2213337210666230420100001

F. Shirini, Sara Haghpanah-Kouchesfehani, Z. Azizi, Nader Daneshvar, H. Tajik

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Abstract

In this article, succinimidinium perchlorate as a new acidic ionic liquid catalyst was prepared and used to synthesize 5-arylidene barbituric acid and pyrano[2,3-d]pyrimidinone derivatives. These two derivatives of barbituric acid have a variety of useful properties. In this article, succinimidinium perchlorate as a new acidic ionic liquid catalyst was prepared, identified and used to synthesize 5-arylidene barbituric acid and pyrano[2,3-d]pyrimidinone derivatives. The advantages of this reagent were high yields, high efficiency, short reaction times, easy performance, easy work-up and reusability. The FT-IR spectra were taken as liquid or made from KBr tablets using the Bruker PS-15 FT-IR. The vibrational frequencies absorbed were reported in cm-1.1H NMR using DMSO as solvent were recorded by a Bruker Avance NMR 500 MHz. 13C NMR spectra were recorded in DMSO using Bruker Avance NMR 125 MHz device. Tetramethylsilane was used as an internal standard. The electrothermal apparatus has been used to measure melting points in degrees Celsius. Mass spectra were performed using Agilent Technologies 5975C spectrometer via mass selective detector (MSD) operating at an ionization potential of 70 eV. Preparation of the catalysts In an ice bath, to a 50 mL round-bottom balloon containing 0.990 g of succinimide (10.0 mmol) in 20.0 mL of dry dichloromethane, perchloric acid (70%, 0.85 mL, 10 mmol) was added drop-wise over 20 minutes. After that, the mixture was stirred at room temperature for 40 minutes. At this stage, the solvent was decanted and a white solid was obtained. The precipitated product was washed 3 times with diethyl ether (3×15.0 mL) to elute the non-ionic residue. Finally, the ionic liquid was dried by vacuum apparatus and keeping in the oven at 60 ̊C for six hours . Succinimidinium perchlorate, which was made for the first time in this project, was identified with different methods, including FT-IR, 1H NMR, 13C NMR and mass spectroscopic techniques

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高氯酸琥珀酰亚胺作为一种新型高效Brönsted酸性离子液体促进剂用于合成5-芳基巴比妥酸和吡喃[2,3-d]嘧啶酮衍生物

本文制备了高氯酸丁二咪铵作为新型酸性离子液体催化剂，用于合成5-芳基巴比妥酸和吡喃[2,3-d]嘧啶酮衍生物。巴比妥酸的这两种衍生物具有多种有用的性质。本文制备了一种新型酸性离子液体催化剂——高氯酸丁二咪铵，对其进行了鉴定，并用于合成5-芳基巴比妥酸和吡喃[2,3-d]嘧啶酮衍生物。该试剂具有收率高、效率高、反应时间短、性能简单、易加工、可重复使用等优点。FT-IR光谱作为液体或由KBr片用Bruker PS-15 FT-IR制成。以DMSO为溶剂，在cm-1.1H NMR中报道了吸收的振动频率，并由Bruker Avance NMR 500 MHz记录。用Bruker Avance核磁共振125 MHz装置在DMSO中记录13C核磁共振光谱。以四甲基硅烷为内标。电热仪器已被用来测量以摄氏度为单位的熔点。质谱采用Agilent Technologies 5975C光谱仪，通过质量选择检测器(MSD)在70 eV电离电位下工作。催化剂的制备在冰浴中，将高氯酸(70%，0.85 mL, 10 mmol)滴入含有0.990 g琥珀酰亚胺(10.0 mmol)和20.0 mL干二氯甲烷的50 mL圆底球囊中，持续20分钟。之后，在室温下搅拌40分钟。在这一阶段，溶剂被倒出，得到白色固体。沉淀产物用乙醚(3×15.0 mL)洗涤3次，洗脱非离子型残留物。最后，采用真空干燥装置对离子液体进行干燥，并在60℃的烘箱中保温6 h。采用FT-IR、1H NMR、13C NMR和质谱等方法对本项目首次合成的高氯酸琥珀酰亚胺进行鉴定

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来源期刊

Current Organocatalysis CHEMISTRY, PHYSICAL-

CiteScore

2.00

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0.00%

发文量

期刊介绍： Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.