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Organic electrochemistry: Synthesis and functionalization of β-lactams in the twenty-first century
Heterocyclic Communications ( IF 2.3 ) Pub Date : 2021-01-01 , DOI: 10.1515/hc-2020-0121
Martina Bortolami 1 , Isabella Chiarotto 1 , Leonardo Mattiello 1 , Rita Petrucci 1 , Daniele Rocco 1 , Fabrizio Vetica 2 , Marta Feroci 1
Affiliation  

Organic electrochemistry is a technique that allows for the heterogeneous redox reactions avoiding both the use of stoichiometric amounts of redox reagents and the resulting formation of stoichiometric by-products. In fact, the redox reagent in these reactions is the electron, which is naturally eco-friendly and produces no side compounds. It is therefore quite obvious that electrochemistry can be classified as a “green” technology. The use of this methodology in the synthesis of β-lactams is not a novelty, but the growing interest in this class of biologically active compounds, due to the discovery of new fields of application (after a moment of decrease in interest due to antibiotic resistance) has been a stimulus for the search for more efficient electrochemical ways to synthesize and transform β-lactams. Thus, this review deals with the twenty-first-century applications of electroorganic technique to the chemistry of β-lactams, by analyzing first the syntheses classified by the type of reactions (cyclization, cycloaddition, etc.) and then by manipulating the β-lactam structure, using it as a synthon. Lastly, the importance of this technique is demonstrated by a study of a pilot plant scale reduction of a cephalosporanic acid derivative to a commercially important antibiotic.

中文翻译:

有机电化学:二十一世纪β-内酰胺的合成与功能化

有机电化学是一种允许异质氧化还原反应的技术,既避免了使用化学计量的氧化还原试剂,又避免了化学计量副产物的形成。实际上,这些反应中的氧化还原试剂是电子,它自然是生态友好的,不会产生任何副化合物。因此,很明显,电化学可以归类为“绿色”技术。这种方法在β-内酰胺类化合物的合成中并不是新颖的,但是由于发现了新的应用领域(在由于抗生素耐药性引起兴趣下降之后),人们对这类生物活性化合物的兴趣日益浓厚。 )一直是人们寻求更有效的电化学方法来合成和转化β-内酰胺的一种刺激。因此,这篇综述通过首先分析按反应类型(环化,环加成等)分类的合成方法,然后通过操纵β-内酰胺结构来研究二十一世纪电有机技术在β-内酰胺化学中的应用。 ,将其用作合成子。最后,这项技术的重要性通过一项对头孢菌酸衍生物降低为商业上重要的抗生素的试验性工厂规模的研究得以证明。
更新日期:2021-01-01
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