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

Abstract

Heterocycles functionalized with pentavalent phosphorus are of great importance since they include a great variety of biologically active compounds and pharmaceuticals, advanced materials, and valuable reactive intermediates for organic synthesis. Significant progress in synthesis of P(O)R2-substituted six-membered heterocycles has been made in the past decade. This review covers the synthetic strategies towards aromatic monocyclic six-membered N-heterocycles, such as pyridines, pyridazines, pyrimidines, and pyrazines bearing phosphonates and phosphine oxides, which were reported from 2012 to 2022.

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

“…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).…”

“…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.…”

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

“…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.…”

“…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] .…”