Application of the Microwave Technique in Continuous Flow Processing of Organophosphorus Chemical Reactions

Bálint, Erika; Tajti, Ádám; Keglevich, György

doi:10.3390/ma12050788

Cited by 25 publications

(19 citation statements)

References 106 publications

(127 reference statements)

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“…α-Hydroxy phosphonate derivatives are of great importance due to their various biological actions and therapeutic applications such as bactericidal [ 5 ], fungicidal [ 6 ], antitumor [ 7 ], and HIV inhibitory activities [ 8 ]. The high interest in this class of compounds has been reflected in numerous publications on their synthesis, modification, and application not only in medical chemistry [ 9 , 10 , 11 , 12 , 13 , 14 ]. It was shown that further functionalization of the hydroxy group has a pivotal impact on the biological activity of the modified α-hydroxy phosphonates.…”

Section: Introductionmentioning

confidence: 99%

Promiscuous Lipase-Catalyzed Markovnikov Addition of H-Phosphites to Vinyl Esters for the Synthesis of Cytotoxic α-Acyloxy Phosphonate Derivatives

et al. 2022

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An enzymatic route for phosphorous-carbon- bond formation is developed by discovering new promiscuous activity of lipase. This biocatalytic transformation of phosphorous-carbon- bond addition leads to biologically and pharmacologically relevant α-acyloxy phosphonates with methyl group in α-position. A series of target compounds were synthesized with yields ranging from 54% to 83% by enzymatic reaction with Candida cylindracea (CcL) lipase via Markovnikov addition of H-phosphites to vinyl esters. We carefully analyzed the best conditions for the given reaction such as the type of enzyme, temperature, and type of solvent. The developed protocol is applicable to a range of H-phosphites and vinyl esters significantly simplifying the preparation of synthetically challenging α-pivaloyloxy phosphonates. Further, the obtained compounds were validated as new potential antimicrobial drugs with characteristic E. coli bacterial strains and DNA modification recognized by the Fpg protein, N-methyl purine glycosylases as new substrates. The impact of the methyl group located in the α-position of the studied α-acyloxy phosphonates on the antimicrobial activity was demonstrated. The pivotal role of this group on inhibitory activity against selected pathogenic E. coli strains was revealed. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics.

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Section: Introductionmentioning

confidence: 99%

Promiscuous Lipase-Catalyzed Markovnikov Addition of H-Phosphites to Vinyl Esters for the Synthesis of Cytotoxic α-Acyloxy Phosphonate Derivatives

et al. 2022

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“…The MW technique proved its significance for enabling faster and more efficient synthesis processes in organic and medicinal chemistry [19]. It is also widely used for the preparation of phosphorus-containing derivatives [20]. In order to decrease the reaction time of the oxidative addition, we studied this transformation under MW conditions.…”

Section: Figure 1 General Structure Of Phosphole Oxides (A) and Benzo[b]phoshole Oxides (B)mentioning

confidence: 99%

Microwave-assisted synthesis of benzo[b]phosphole oxide derivatives by oxidative addition of acetylenes and secondary phosphine oxides or alkyl phenyl-H-phosphinates

et al. 2021

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“…Microwave (MW) heating coupled to a flow reactor was reported for providing a readily scalable process compared to a conventional batch microwave system. [37] Jansa, Janeba and co-workers developed a batch MW-assisted method for the hydrolysis of acyclic nucleoside phosphonate diesters towards the corresponding…”

Section: Hydrolysis and Transesterification Reactionsmentioning

confidence: 99%

Continuous Flow Organophosphorus Chemistry

2020

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Organophosphorus derivatives are widespread compounds that chemists find from the bench to the plant, with numerous daily life applications. Besides their common utility for a wide range of notorious reactions such as the Wittig and Horner‐Wadsworth‐Emmons olefinations, the Arbuzov reaction, the Staudinger reaction, the Mitsunobu reaction as well as ligands for a large variety of organometallic complexes, organophosphorus compounds have also found numerous applications as active pharmaceutical ingredients and agrochemicals. Some organophosphorus derivatives are also infamously known as Chemical Warfare Agents. Within the context of generalized adoption of new process technologies in the Chemistry Toolbox, this review intends to give an update on the most recent and significant advances in continuous flow organophosphorus chemistry. Selected examples in methodology, total synthesis and for the preparation of industrially relevant targets are discussed for illustrating the assets of flow chemistry.

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Application of the Microwave Technique in Continuous Flow Processing of Organophosphorus Chemical Reactions

Cited by 25 publications

References 106 publications

Promiscuous Lipase-Catalyzed Markovnikov Addition of H-Phosphites to Vinyl Esters for the Synthesis of Cytotoxic α-Acyloxy Phosphonate Derivatives

Promiscuous Lipase-Catalyzed Markovnikov Addition of H-Phosphites to Vinyl Esters for the Synthesis of Cytotoxic α-Acyloxy Phosphonate Derivatives

Microwave-assisted synthesis of benzo[b]phosphole oxide derivatives by oxidative addition of acetylenes and secondary phosphine oxides or alkyl phenyl-H-phosphinates

Continuous Flow Organophosphorus Chemistry

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