Synthesis of highly substituted quinolines via heterocyclization of fluorinated acetylenephosphonates with ortho-aminoaryl ketones

Duda, Blazej; Tverdomed, Sergey N.; Bassil, Bassem S.; Röschenthaler, Gerd‐Volker

doi:10.1016/j.tet.2014.08.027

Cited by 19 publications

(5 citation statements)

References 95 publications

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“…The synthesis of substituted quinolin-3-ylphosphonates 803 and 806 can be achieved through a stereoselective cyclization between orto -aminobenzaldehyde imines 801 or ortho -aminoaryl ketones 804 and alkynylphosphonates 802 and 805 . The developed protocols use K 2 CO 3 or Li 2 CO 3 /TMEDA for the construction of fluorinated quinolines with XCF 2 -alkynylphosphonates (Scheme , Table ).…”

Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search in the development of synthetic routes for obtaining novel members of this family of compounds. This updated review covers methodologies established since 2004, focusing on the synthesis of azaheterocyclic phosphonates, of which the phosphonate moiety is directly substituted onto to the azaheterocyclic structure. Emphasizing recent advances, this review classifies newly developed synthetic approaches according to the ring size and providing information on biological activities whenever available. Furthermore, this review summarizes information on various methods for the formation of C–P bonds, examining sustainable approaches such as the Michaelis–Arbuzov reaction, the Michaelis–Becker reaction, the Pudovik reaction, the Hirao coupling, and the Kabachnik–Fields reaction. After analyzing the biological activities and applications of azaheterocyclic phosphonates investigated in recent years, a predominant focus on the evaluation of these compounds as anticancer agents is evident. Furthermore, emerging applications underline the versatility and potential of these compounds, highlighting the need for continued research on synthetic methods to expand this interesting family.

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Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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“…The highly electrophilic distal fluorinated iminium indeed undergoes attack by the aryl substituent of the remote nitrogen, in a Friedel-Crafts-type reaction, to finally afford 2,4-bis(fluoroalkyl)quinolines after rearomatization. The synthesis of quinoline derivatives bearing two fluorinated groups in both positions 2 and 4 is scarcely described; only syntheses of bis(trifluoromethylated)quinolines were reported [ 97 , 98 , 99 , 100 ]. The use of FARs allowed to prepare in one step, from two series of variously substituted aryl fluoroketimines 106a – l and 107a – u , a large diversity of 2,4-bis(fluoroalkyl)quinolines 109a – l and 110u bearing different fluorinated groups on the pyrido moiety and various substituents on the benzo ring under mild conditions.…”

Section: Fluoroalkyl Amino Reagents: Efficient Tools For Fluorinatmentioning

confidence: 99%

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

et al. 2017

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Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS) onto heterocycles. In this context, fluoroalkyl amino reagents (FARs)—a class of chemicals that was slightly forgotten over the last decades—has emerged again recently and proved to be a powerful tool for the introduction of various fluorinated groups onto (hetero)aromatic derivatives.

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“…Although many 1-aryl-2-(trifluoromethyl)ethynes are found in synthetic, pharmaceutical, and material products, 1 the corresponding 1-(trifluoromethyl)-2-(phenylthio)ethynes are very few in number. Furthermore, general protocols for the synthesis of these compounds have not been developed to date; indeed, to the best of our knowledge, the syntheses of 1-(trifluoromethyl)-2-(phenylthio)ethynes have only been reported on three occasions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Highly regio- and stereocontrolled preparation of α-(trifluoromethyl)-β-(phenylthio) enamines by the hydroamination of in situ-synthesized 1-(trifluoromethyl)-2-(phenylthio)ethyne

Koga,

Matsuda,

Tanaka

et al. 2023

Org. Biomol. Chem.

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Synthesis of highly substituted quinolines via heterocyclization of fluorinated acetylenephosphonates with ortho-aminoaryl ketones

Cited by 19 publications

References 95 publications

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

Highly regio- and stereocontrolled preparation of α-(trifluoromethyl)-β-(phenylthio) enamines by the hydroamination of in situ-synthesized 1-(trifluoromethyl)-2-(phenylthio)ethyne

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