Synthesis of Phosphorus(V)-Substituted Six-Membered N-Heterocycles: Recent Progress and Challenges

Volkova, Yu. A.; Заварзин, И. В.

doi:10.3390/molecules28062472

Cited by 6 publications

(4 citation statements)

References 137 publications

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“…Early in 2023, Volkova covered the different methods for the synthesis of phosphorus(V)substituted six-membered N-heterocycles from 2012 up to the end of 2022. 267 In this section, we describe the strategies that have been developed to access new members of this huge family in recent years. The compounds of interest were synthesized using a solventfree Kabachnik−Fields reaction catalyzed by magnesium perchlorate (Scheme 105).…”

Section: Introductionmentioning

confidence: 99%

“…Regarding the synthetic methodologies for the construction of these compounds, Zeni et al presented a summary on the synthesis of six-membered N-heterocycles from alkynes and nitrogen source, which includes a select number of phosphonylated piperidine and quinoline examples. Early in 2023, Volkova covered the different methods for the synthesis of phosphorus(V)-substituted six-membered N-heterocycles from 2012 up to the end of 2022 . In this section, we describe the strategies that have been developed to access new members of this huge family in recent years.…”

Section: Introductionmentioning

confidence: 99%

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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: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

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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“…Phosphorus-substituted heterocycles constitute an important group of organophosphorus compounds [1] and have a wide variety of biological activities. [2] These compounds have been widely studied for their applications in different fields, including drug discovery, electrochemical catalysis, synthetic chemistry, and more. [3][4][5][6][7][8] One such example is the quantum chemical (QC) study of the phosphorus substitution at various sites in the barbaralane molecule, which undergoes a degenerate cope rearrangement.…”

Section: Introductionmentioning

confidence: 99%

“…oli dHeterocycles are known to be biologically and industrially important compounds. Phosphorus‐substituted heterocycles constitute an important group of organophosphorus compounds [1] and have a wide variety of biological activities [2] . These compounds have been widely studied for their applications in different fields, including drug discovery, electrochemical catalysis, synthetic chemistry, and more [3–8] .…”

Section: Introductionmentioning

confidence: 99%

Exploring the Influence of the Phosphorus‐Heteroatom Substitution in Nicotine on Its Electronic and Vibrational Spectroscopic Properties

Taherivardanjani,

Wylie,

Dötzer

et al. 2023

Chemistry A European J

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The influence of phosphorus substitution of nitrogen in heterocyclic compounds on the vibrational spectroscopy as well as frontier molecular orbitals are analyzed. Nicotine with two nitrogen atoms in its structure is taken as the sample system to be studied computationally. By replacing the nitrogen atom in one or both rings of this molecule with phosphorus, three nicotine derivatives are created. The vibrational circular dichroism and infrared spectra of these four molecules in their monomer state, as well as the assemblies up to trimers are determined. The aforementioned spectra are calculated using static quantum chemical calculations employing a cluster‐weighted approach. The calculated gas phase spectra of nicotine are compared to their respective experimental spectra. It is observed that the nicotine derivatives with phosphorus in the methylpyrrolidine ring have considerably different gas phase and bulk phase vibrational circular dichroism spectra when compared to nicotine. The phosphorus substitution reduces the energy gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital as well as altering the polarizability and reactivity of the investigated molecules.

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Phosphorus Heterocycles and Their Biological Applications

Kumar,

Mukhopadhyay,

Bhagat

2024

ChemistrySelect

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Life of the living organism is based on phosphorous, and it is involved in almost all important biological and biochemical processes such as energy transfer, bone development and storing genetic information. Many of the therapeutic agents having C─P bond, isolated naturally as well and widely used in daily clinical practices are phosphorus‐containing drugs (e.g: phosphotriesters, phosphonates, phosphinates, phosphine oxides, phosphoric amides, bisphosphonates, phosphoric anhydrides, etc.) and growing further. The phosphorus heterocycles (PHs) integrate the merits of both phosphorus atom and heterocyclic scaffolds representing an important class of organophosphorus compounds, which are constantly drawing the attention among both industrial and scientific society as these compounds have shown varieties of related applications. Owing to its seminal biological importance PHs have inspired a whole generation of medicinal chemists to come up with novel scaffolds containing phosphorous atom. This review is focused mainly on the compilation of different classes of bioactive phosphorus containing heterocyclic skeletons (which includes phosphorus atom within the heterocyclic ring system or as substituted phosphorus atom attached with another heterocyclic ring system) having both therapeutic and other material chemistry applications since the year 2000 onwards barring their synthetic routes.

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Synthesis of Phosphorus(V)-Substituted Six-Membered N-Heterocycles: Recent Progress and Challenges

Cited by 6 publications

References 137 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

Exploring the Influence of the Phosphorus‐Heteroatom Substitution in Nicotine on Its Electronic and Vibrational Spectroscopic Properties

Phosphorus Heterocycles and Their Biological Applications

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