First ligand-free, microwave-assisted, Heck cross-coupling reaction in pure water on a nucleoside – application to the synthesis of antiviral BVDU

Hervé, Gwénaëlle; Len, Christophe

doi:10.1039/c4ra09798j

Cited by 41 publications

(15 citation statements)

References 39 publications

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“…Brivudine (BVDU) is an antiviral nucleoside analog used in the treatment of herpes zoster virus (HSV-1). Hervé et al in 2014 reported the synthesis of BVDU using a Pd-catalyzed Heck alkenylation reaction in 56% yield by using 10 mol% of Pd(OAc) 2 as a catalyst [52]. With a highly active catalytic system in hand, we explored the possibility of addressing the issues related to BVDU synthesis such as lower yields and the use of a high catalyst concentration.…”

Section: Synthesis Of Antiviral Drug Brivudine (Bvdu) Using Catmentioning

confidence: 99%

“…This effort led to the synthesis of 33 modified nucleosides using a single catalytic system with potential for further scale-up. alkenylation reaction in 56% yield by using 10 mol% of Pd(OAc)2 as a catalyst [52]. With a highly active catalytic system in hand, we explored the possibility of addressing the issues related to BVDU synthesis such as lower yields and the use of a high catalyst concentration.…”

Section: Suzuki-miyaura Cross Coupling On Four Natural Nucleosides Usmentioning

confidence: 99%

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Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Bhilare

Shet

Sanghvi³

et al. 2020

Molecules

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Nucleic acid derivatives are imperative biomolecules and are involved in life governing processes. The chemical modification of nucleic acid is a fascinating area for researchers due to the potential activity exhibited as antiviral and antitumor agents. In addition, these molecules are also of interest toward conducting useful biochemical, pharmaceutical, and mutagenic study. For accessing such synthetically useful structures and features, transition-metal catalyzed processes have been proven over the years to be an excellent tool for carrying out the various transformations with ease and under mild reaction conditions. Amidst various transition-metal catalyzed processes available for nucleoside modification, Pd-catalyzed cross-coupling reactions have proven to be perhaps the most efficient, successful, and broadly applicable reactions in both academia and industry. Pd-catalyzed C–C and C–heteroatom bond forming reactions have been widely used for the modification of the heterocyclic moiety in the nucleosides, although a single catalyst system that could address all the different requirements for nucleoside modifications isvery rare or non-existent. With this in mind, we present herein a review showcasing the recent developments and improvements from our research groups toward the development of Pd-catalyzed strategies including drug synthesis using a single efficient catalyst system for the modification of nucleosides and other heterocycles. The review also highlights the improvement in conditions or the yield of various bio-active nucleosides or commercial drugs possessing the nucleoside structural core. Scale ups wherever performed (up to 100 g) of molecules of commercial importance have also been disclosed.

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Section: Synthesis Of Antiviral Drug Brivudine (Bvdu) Using Catmentioning

confidence: 99%

Section: Suzuki-miyaura Cross Coupling On Four Natural Nucleosides Usmentioning

confidence: 99%

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Bhilare

Shet

Sanghvi³

et al. 2020

Molecules

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show abstract

“…In 2014, for the first time, Len et al reported a palladium catalyzed Heck cross-coupling reaction between 5-iodo-2ʹ-deoxyuridine and various acrylate derivatives using ligand-free conditions and assisted-microwaves in pure water [20]. Those new conditions allowed a totally aqueous access to antiviral BVDU.…”

Section: Pd(ii)-catalyzed Heck Cross-coupling In H 2 Omentioning

confidence: 99%

Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Hervé

Len

2015

Sustain Chem Process

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Amongst all synthetic nucleosides having high potential biological activities, C5-modified pyrimidines and C7-deaza or C8-modified purines have been particularly studied. These main chemical modifications have been developed using palladium cross-coupling reactions. This review focus on both Heck and Sonogashira cross-coupling of nucleosides using different aspects of the twelve principles of green chemistry: use of aqueous medium and no protection/deprotection steps.

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“…The reaction of 5-iodo-2'-deoxyuridine (2) with various acrylate derivatives was carried out in the presence of Pd(OAc) 2 (Scheme 2.2) [3,4]. The use of task-specific ionic liquids (ILs) is also a "hot topic".…”

Section: Heck Reactionmentioning

confidence: 99%

Microwave-Assisted Syntheses in Organic Chemistry

Kiss

Bálint²,

Keglevich

2016

SpringerBriefs in Molecular Science

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The second part focuses on the summary of typical organic chemical reactions selected, such as coupling reactions (C-C bond formation reactions, carbon-heteroatom bond formations), condensations (aldol-type-, Claisen-, Knoevenagel reaction), multicomponent reactions (Mannich-, Biginelli-, Hantzsch-, Bucherer-Bergs-, Strecker-, Gewald-, Kabachnik-Fields-, Kindler-, Passerini-, Ugi-and domino reactions), cycloadditions (including Diels-Alder reactions). The authors tried to compile fashionable reactions that have been reviewed less in the past years.

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First ligand-free, microwave-assisted, Heck cross-coupling reaction in pure water on a nucleoside – application to the synthesis of antiviral BVDU

Abstract: For the first time, a palladium catalyzed Heck cross-coupling reaction between 5-iodo-2′-deoxyuridine and various acrylate derivatives was performed using ligand-free conditions and microwave assistance in pure water.

Cited by 41 publications

References 39 publications

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Microwave-Assisted Syntheses in Organic Chemistry

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