Synthesis of oligophosphonate aromatic systems using the Michaelis-Arbuzov reaction and microwave radiation

Serkova, O. S.; Kamkina, A. V.; Sivkova, Anastasia S.; Maslennikova, V. I.

doi:10.1080/10426507.2019.1618299

Cited by 1 publication

(1 citation statement)

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“…As with many other cases in organic chemistry, the microwave (MW) irradiation also facilitates the MA reaction, since it reduces the time, increases the yield, and simplifies the workup [ 59 , 60 ]. Further, MW irradiation facilitates the reaction between heteroaryl halides and phosphites and has been applied for the synthesis of 1,3,5-triazinylphosphonic acids ( Scheme 34 ) as new non-cytotoxic antiviral agents with, however, low to moderate activities against influenza virus H1N1 and H3N2 (the IC 50 values were approximately 9–19-fold higher than the oseltamivir, the currently approved drug for influenza) [ 61 ].…”

Section: Improvements In and Variations Of The Ma Reactionmentioning

confidence: 99%

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

Kostoudi

Pampalakis

2022

IJMS

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Compounds bearing the phosphorus–carbon (P–C) bond have important pharmacological, biochemical, and toxicological properties. Historically, the most notable reaction for the formation of the P–C bond is the Michaelis–Arbuzov reaction, first described in 1898. The classical Michaelis–Arbuzov reaction entails a reaction between an alkyl halide and a trialkyl phosphite to yield a dialkylalkylphosphonate. Nonetheless, deviations from the classical mechanisms and new modifications have appeared that allowed the expansion of the library of reactants and consequently the chemical space of the yielded products. These involve the use of Lewis acid catalysts, green methods, ultrasound, microwave, photochemically-assisted reactions, aryne-based reactions, etc. Here, a detailed presentation of the Michaelis–Arbuzov reaction and its developments and applications in the synthesis of biomedically important agents is provided. Certain examples of such applications include the development of alkylphosphonofluoridates as serine hydrolase inhibitors and activity-based probes, and the P–C containing antiviral and anticancer agents.

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Section: Improvements In and Variations Of The Ma Reactionmentioning

confidence: 99%