Synthesis and Application of <i>N</i>-Tosyl Piperidinyl-Containing α-Aminophosphonates

Jiang, Zhifu; Zhao, Jian; Gao, Beibei; Chen, Shuo; Qu, Wen‐Yan; Mei, Xiangdong; Rui, Changhui; Ning, Jun; She, Dongmei

doi:10.1080/10426507.2012.729236

Cited by 13 publications

(7 citation statements)

References 37 publications

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“…In this way a one-pot three-component reaction between 1-tosylpiperidine-4-one ( 34 ), aromatic amines 35 and diethyl phosphonate in the presence of magnesium perchlorate as a catalyst, under neat conditions at 80 °C afforded α-aminophosphonates 36 in good yields ( Scheme 10 ). Some of the resulting α-aminophosphonates showed insecticidal activity against Plutella xylostella [ 36 ].…”

Section: Reviewmentioning

confidence: 99%

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Haji¹

2016

Beilstein J. Org. Chem.

148

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SummaryMulticomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

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Section: Reviewmentioning

confidence: 99%

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Haji¹

2016

Beilstein J. Org. Chem.

148

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“…The compounds of interest were synthesized using a solvent-free Kabachnik–Fields reaction catalyzed by magnesium perchlorate (Scheme ). While some of the compounds showed moderate insecticidal activity, they were much less active than commercially known products such as Fipronil …”

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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“…These organophosphorus compounds are known to exhibit a wide array of biological properties including antimicrobial activity, [56][57][58][59][60][61][62][63] antimalarial activity, 66 antitumor activity, 64,65,[67][68][69][70] and enzymatic-inhibitory activity against rennin, 71 serine protease, 61,70 dialkylglycine decarboxylase 72 , leucine aminopeptidase, 73 , among many others. [74][75][76][77][78][79][80] Certain α-aminophosphonate derivatives showed efficacy in designing continuous drug-release systems due to their ability to enhance the membrane permeability of a hydrophilic probe molecule. 81 In addition, α-functionalized phosphonic-acid esters serve as synthones for many organic compounds and dyes in phosphonate chemistry, and also find use in laser technology, and as fluorescent materials for visualization of biomolecules.…”

Section: Synthesis Of α-Aminophosphonatesmentioning

confidence: 99%

Green-inspired synthetic drives for organophosphorus compounds under solvent-free conditions

Brahmachari¹,

Karmakar²

2022

Arkivoc

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Organophosphorus chemistry is an exciting field of research. Phosphorus-functionalized organic molecules find practical and useful applications in such diverse areas as medicinal, pharmaceutical, agrochemical, and materials chemistries, both on laboratory and industrial scales. Green-chemistry principles are motivating the design and development of newer synthetic methodologies for such beneficial organophosphorus compounds and their analogues. Solvent-free conditions are associated with several practical benefits, including operational simplicity, cost-effectiveness, minimization of waste generation, and reduced pollution, all of which are very much crucial for industrial process development. This review summarizes solvent-free synthetic methodologies for functionalized organophosphorus compounds reported during the period 2016 through 2021.

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Synthesis and Application of N-Tosyl Piperidinyl-Containing α-Aminophosphonates

Cited by 13 publications

References 37 publications

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

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

Green-inspired synthetic drives for organophosphorus compounds under solvent-free conditions

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