Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles

Safina, L. Yu.; Селиванова, Г. А.; Bagryanskaya, I. Yu.; Shteingarts, V. D.

doi:10.1007/s11172-009-0134-z

Cited by 9 publications

(2 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among the four possible sites at ring A, position 4 (corresponding to position 8 of the quinoline core) appeared most interesting for the envisaged nucleophilic replacement of a fluorine atom with an amino substituent, as there have been several reports describing the preferential attack of nitrogen nucleophiles at this position in various di- and trifluoroquinolines [ 24 , 25 , 26 , 27 ]. We therefore commenced our investigations by preparing the hitherto unknown 4-fluoro derivative of Luotonin A via the pathway depicted in Scheme 1 , starting from the quinazolinonecarboxylic acid ester 1 [ 21 , 28 ].…”

Section: Resultsmentioning

confidence: 99%

A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives

et al. 2017

View full text Add to dashboard Cite

An oxidative ring opening reaction of the central ring C in the alkaloid Luotonin A and two of its derivatives was found to occur upon heating with an excess amine and potassium carbonate in dimethylsulfoxide (DMSO) solution in the presence of air oxygen. The structure of the novel amide-type products was elucidated and a possible mechanism for this reaction is proposed. Four of the new compounds show moderate in vitro anticancer activity towards human colon adenocarcinoma cells.

show abstract

Section: Resultsmentioning

confidence: 99%

A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives

et al. 2017

View full text Add to dashboard Cite

show abstract

“…8,9 Thanks to this, the area of quinolines and their functional derivatives polyfluorinated on a benzene ring has been opened for intensive elaboration. [9][10][11][12][13] We believed this methodology is possible to apply to N-acetyl derivatives of perfluoronaphthylamines for preparing their less fluorinated analogues unsubstituted ortho to an amino group as potential building blocks for polyfluoronaphthoazaheterocycles, some of which also can be highly biologically active (for example, by analogy with mono-and difluorobenzoquinolines 14 ).…”

Section: Introductionmentioning

confidence: 99%

Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: synthetic outcomes and mechanistic considerations

Reshetov¹,

Селиванова²,

Politanskaya³

et al. 2011

Arkivoc

View full text Add to dashboard Cite

Dedicated to Professor Usein M Dzhemilev on the occasion of his 65th birthday AbstractReduction of the N-acetyl derivatives of heptafluoro-2-naphthylamine and its less fluorinated analogues by zinc in aqueous NH 3 has been investigated as a possible general and concise route to partially fluorinated N-(2-naphthyl)acetamides and, accordingly, 2-naphthylamines inaccessible by other ways. Quantum chemical calculations and CV measurement results have been used to discuss and justify the suggested reaction mechanism including two competing routes: fragmentation of a substrate radical anion and its complex with a zinc cation.

show abstract

Modern Fluorine‐Containing Agrochemicals

Pazenok

Bernier

Donnard

et al. 2022

Patai's Chemistry of Functional Groups

View full text Add to dashboard Cite

Today, modern fluorine‐containing agrochemicals are of the utmost importance to control weeds, insect pests, and many plant diseases and, ultimately, to ensure sustainable yields, thereby securing the food supply for a growing world population. Over the past two decades, new fluorine‐containing pesticides have gained a significant market share, reflecting the enormous global economic success of modern crop protection. But despite the commercialization of many highly potent pesticides, new regulatory requirements and the need for new modes of action and resistance‐breaking products are still driving efforts to identify and introduce new compounds with even better efficacy and safety profiles. This chapter describes the structures, chemotypes, modes of action, and syntheses of some of the newest organofluorine agrochemicals (fungicides, herbicides, and insecticides) recently commercialized or under development. The main objective of this review is to describe the evolutionary approaches of the latest generation of “small molecule” fluorinated pesticides as well as the associated synthetic challenges. This chapter also describes new and “old” fluorine‐containing building blocks and focuses on their synthetic accessions for subsequent incorporation into large‐scale production of agrochemical active ingredients. Since the majority of modern agrochemicals are protected by patents, the analysis of chemical processes in this review is primarily based on the original patent literature. Commercial production of crop protection compounds requires robust, environmentally friendly, safe, and ultimately economically viable processes. Numerous process patents impressively demonstrate how producers have met these criteria, solved synthesis problems, and ultimately developed pathways to economically viable agrochemical manufacturing. Finally, this review also aims to demonstrate the impact of fluorination on the environmental fate and possible metabolism pathways of certain fluorinated pesticides, with or without the release of polyfluoroalkyl carboxylic acids.

show abstract

Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles

Cited by 9 publications

References 29 publications

A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives

A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives

Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: synthetic outcomes and mechanistic considerations

Modern Fluorine‐Containing Agrochemicals

Contact Info

Product

Resources

About