Atom efficient synthesis of pyrimidine and purine nucleosides by ball milling

Crossey, Kerri; Cunningham, Richard; Redpath, Philip; Migaud, Marie E.

doi:10.1039/c5ra12239b

Cited by 19 publications

(9 citation statements)

References 25 publications

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“…[12,13] In its broadest terms, mechanochemistrydates back two millennia; [14] however,o nly in recent decadesh as it experienced ar enaissance. [18][19][20][21][22][23][24][25][26] Despite its long history and recents uccesses, these methodologies remain largely unexploredf or the synthesis of main-group compounds, with only works by Peters et al [27] andH anusa et al [22,28] on organometallic complexes.W er ecently reported af ast and high-yielding, multi-step, orthogonal mechanochemicals ynthesis of indium(III)c omplexes, [29] and demonstrated the value of this technique in enabling the isomerisation of as terically encumbered phosphazane. [18][19][20][21][22][23][24][25][26] Despite its long history and recents uccesses, these methodologies remain largely unexploredf or the synthesis of main-group compounds, with only works by Peters et al [27] andH anusa et al [22,28] on organometallic complexes.W er ecently reported af ast and high-yielding, multi-step, orthogonal mechanochemicals ynthesis of indium(III)c omplexes, [29] and demonstrated the value of this technique in enabling the isomerisation of as terically encumbered phosphazane.…”

Section: Introductionmentioning

confidence: 99%

“…In its broadest terms, mechanochemistry dates back two millennia; however, only in recent decades has it experienced a renaissance . Recent advances in the field have illustrated its potential to unlock novel organic transformations and otherwise inaccessible molecules . Despite its long history and recent successes, these methodologies remain largely unexplored for the synthesis of main‐group compounds, with only works by Peters et al .…”

Section: Introductionmentioning

confidence: 99%

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Mechanochemical Synthesis of Phosphazane‐Based Frameworks

Sim

Shi

Ganguly

et al. 2017

Chemistry A European J

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Mechanochemistry is emerging as a powerful solvent-free approach to chemical synthesis, having been applied to metal oxides, pharmaceutical materials, organic compounds and to a lesser extent, coordination complex synthesis. Notably, examples of applications of mechanochemical methodologies in the synthesis of main-group compounds are few and far between. Herein, we demonstrate that ball milling enabled the solvent-free synthesis of a range of phosphazane frameworks with a broad substrate scope, yielding seven new acyclic and macrocyclic species. The strength of this methodology is highlighted by a fast, selective and high-conversion product generation from poorly soluble starting materials, thereby demonstrating mechanochemistry as a real alternative to solution-based methods in synthetic main-group chemistry.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis of Phosphazane‐Based Frameworks

Sim

Shi

Ganguly

et al. 2017

Chemistry A European J

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“…Such reactivity is an exciting example of the use of mechanochemistry to activate metals, an approach familiar in inorganic mechanochemistry that is rapidly becoming popular in organic catalysis and chemistry of main group and transition elements . Other recent examples of mechanochemical organic reactions include the syntheses of benzimidazoles, solvent‐free Strecker reactions, the syntheses and functionalization of nucleosides and nucleotides, the oleation of lignin, polymer synthesis through polycondensation reactions, and the synthesis of bis(arylimino)acenaphthalene ligands for redox‐active complexes …”

Section: From Classical Organic Transformation To New Reactivitymentioning

confidence: 99%

Mechanochemistry for Organic Chemists: An Update

2017

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“…Regioselective and stereoselective glycosidation of adenine, N 6 -benzoyladenine, N 4 -benzoylcytosine, thymine and uracil to the corresponding β- N 9 -purine or β- N 1 -pyrimidine ribosides was achieved on gram scales under Vorbrüggen-type conditions using LAG ( Scheme 9 ) [ 45 ].…”

Section: Reviewmentioning

confidence: 99%

Mechanochemistry of nucleosides, nucleotides and related materials

Eguaogie¹,

Vyle²,

Conlon³

et al. 2018

Beilstein J. Org. Chem.

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The application of mechanical force to induce the formation and cleavage of covalent bonds is a rapidly developing field within organic chemistry which has particular value in reducing or eliminating solvent usage, enhancing reaction rates and also in enabling the preparation of products which are otherwise inaccessible under solution-phase conditions. Mechanochemistry has also found recent attention in materials chemistry and API formulation during which rearrangement of non-covalent interactions give rise to functional products. However, this has been known to nucleic acids science almost since its inception in the late nineteenth century when Miescher exploited grinding to facilitate disaggregation of DNA from tightly bound proteins through selective denaturation of the latter. Despite the wide application of ball milling to amino acid chemistry, there have been limited reports of mechanochemical transformations involving nucleoside or nucleotide substrates on preparative scales. A survey of these reactions is provided, the majority of which have used a mixer ball mill and display an almost universal requirement for liquid to be present within the grinding vessel. Mechanochemistry of charged nucleotide substrates, in particular, provides considerable benefits both in terms of efficiency (reducing total processing times from weeks to hours) and by minimising exposure to aqueous conditions, access to previously elusive materials. In the absence of large quantities of solvent and heating, side-reactions can be reduced or eliminated. The central contribution of mechanochemistry (and specifically, ball milling) to the isolation of biologically active materials derived from nuclei by grinding will also be outlined. Finally non-covalent associative processes involving nucleic acids and related materials using mechanochemistry will be described: specifically, solid solutions, cocrystals, polymorph transitions, carbon nanotube dissolution and inclusion complex formation.

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Atom efficient synthesis of pyrimidine and purine nucleosides by ball milling

Cited by 19 publications

References 25 publications

Mechanochemical Synthesis of Phosphazane‐Based Frameworks

Mechanochemical Synthesis of Phosphazane‐Based Frameworks

Mechanochemistry for Organic Chemists: An Update

Mechanochemistry of nucleosides, nucleotides and related materials

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