Synthesis and properties of sildenafil isostere

Su, Ziqi; Zhang, Qi; Zhao, Qieqiang; Liu, Wenyi; Zhao, Tao; Wang, Huiping; Li, Jiarong; Xu, Jingyi

doi:10.1002/ardp.202100145

Cited by 3 publications

(1 citation statement)

References 21 publications

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“…Fluorinated chemicals such as 1H-pyrazoles, 3amino-pyrrolidines, and alexipharmic derivatives are made from it. 1,1-Difluoro acetone is the base of numerous vital fungicides, including fluopyrazole succinate, 2-fluorobenzcarboxamide succinic anhydride, and 2-fluorobutyrate succinic anhydride (Su et al, 2021). Methyl iodide combines with acetone to generate CH3COCH2F, which is oxidized to 1,1-difluoro acetone by oxygen or air (Golovanov et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

An elementary study of the industrialized preparation of 1,1-difluoro acetone: Starting material of fluoropyrazole succinate dehydrogenase inhibitor

Lin,

Chai,

Cao

et al. 2023

Int. j. adv. appl. sci.

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In recent years, the development and increasing market presence of fungicides incorporating a fluoropyrazole ring, recognized as succinate dehydrogenase inhibitor fungicides, has gained momentum. The fluoropyrazole ring stands as the foundational nucleus of these fungicides, with its production cost being a pivotal concern for chemical industries. Significantly, the cost of 1,1-difluoro acetone largely influences this manufacturing cost. A cost-effective availability of 1,1-difluoro acetone could revolutionize the current methodologies for fluoropyrazole ring synthesis, primarily due to its enhanced safety and environmental sustainability. This study introduces an industrialized production methodology for 1,1-difluoro acetone, underlining its economic efficiency. Originating from ethyl acetoacetate, dibromide is synthesized in n-heptanol through the Oxone/KBr system. Following a fluorine-bromine exchange reaction with potassium fluoride, difluoride is obtained. Subsequent hydrolysis of the difluoride using 50% sulfuric acid leads to the formation of 1,1-difluoro acetone. Notably, while bromination and fluorination stages employ tubular reactors, hydrolysis, and decarboxylation are achieved in standard reactors. Optimal bromination conditions were identified as 2.2 equivalent bromination reagent, temperature>60℃, and atmospheric pressure. The fluorination conditions mirror those of bromination, with the fluorinating agent being 2.2 equivalent and a reaction temperature of 150℃. For hydrolysis and decarboxylation, 50% sulfuric acid concentration at 90℃ was optimal, yielding a crude product with a 99.60% G.C. content and a 91.25% efficiency. The outlined production process of 1,1-difluoro acetone boasts remarkable cost efficiency and procedural simplicity, positioning it favorably for industrial applications. This innovative approach promises significant manufacturing cost reductions, endowing fungicides with a fluoropyrazole ring a competitive edge in the market. Such advancements are anticipated to foster market expansion, ultimately benefiting agricultural practitioners.

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Section: Introductionmentioning

confidence: 99%

An elementary study of the industrialized preparation of 1,1-difluoro acetone: Starting material of fluoropyrazole succinate dehydrogenase inhibitor

Lin,

Chai,

Cao

et al. 2023

Int. j. adv. appl. sci.

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Nitrosamine Impurities in Herbal Formulations: A Review of Risks and Mitigation Strategies

et al. 2023

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Nitrosamines are a class of chemical compounds that have been found to be impurities in a variety of pharmaceutical products. These impurities have raised concerns due to their potential carcinogenic effects. Recent studies have identified nitrosamines as impurities in a number of pharmaceutical products including angiotensin II receptor blockers (ARBs) and proton pump inhibitors (PPIs). The presence of nitrosamines in these products has led to recalls and market withdrawals. In addition to pharmaceuticals, nitrosamines have also been found in some herbal medicines particularly those containing traditional Chinese medicinal ingredients. The presence of nitrosamines in herbal formulations poses a significant risk to public health and highlights the need for quality control and regulations in the herbal drug industry. The present review article aims to discuss nitrosamine impurities (NMI) prominent causes, risks and scientific strategies for preventing NMI in herbal formulations. The primary objective of this study is to examine the origins of nitrosamine contamination in herbal formulations, the risks associated with these contaminants, and the methods for reducing them. The significance of thorough testing and examination before releasing herbal products to the public is also emphasized. In conclusion, the presence of nitrosamines is not limited to pharmaceutical products and poses a significant threat to the safety of herbal drugs as well. Adequate testing and extensive research are crucial for producing and distributing herbal medicines to the general population.

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Discovery and Development of a Class of New Conversion (PDF) in Friedländer Condensation of o-aminonitrile with Carbonyl Compounds

Duan,

Zhang,

et al. 2023

COC

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Since the discovery of the new conversion, through intramolecular Pinner to Dimroth rearrangement to form a new skeleton product of dihydroquinazolinone in the normal reaction of Friendländer quinoline synthesis of o-aminonitriles and carbonyl compounds, systematic studies have shown that this conversion is a fast and efficient method for the synthesis of nitrogen-containing heterocyclic compounds, especially pyrimidinone derivatives. In 2008, we named this new transformation as a PDF conversion (a new conversion of dihydroquinolinone skeleton compounds formed from intramolecular Pinner to Dimroth rearrangement in the Friedländer quinoline synthesis). In this review, the research progress of PDF conversion is systematically summarized from the following aspects: the discovery of PDF conversion, the determination of the structure of new conversion products, the mechanism of PDF conversion, a new type of organic bifurcation reaction, controllable PDF conversion, the breakthrough of conventional PDF transformation forms, and the application of PDF conversion.

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Synthesis and properties of sildenafil isostere

Cited by 3 publications

References 21 publications

An elementary study of the industrialized preparation of 1,1-difluoro acetone: Starting material of fluoropyrazole succinate dehydrogenase inhibitor

An elementary study of the industrialized preparation of 1,1-difluoro acetone: Starting material of fluoropyrazole succinate dehydrogenase inhibitor

Nitrosamine Impurities in Herbal Formulations: A Review of Risks and Mitigation Strategies

Discovery and Development of a Class of New Conversion (PDF) in Friedländer Condensation of o-aminonitrile with Carbonyl Compounds

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