Synthesis of Furo[2,3‐<i>b</i>]pyrazine Nucleoside Analogues with 1,2,3‐Triazole Linkage

Ermolat’ev, Denis S.; Mehta, Vaibhav P.; Eycken, Erik V. Van der

doi:10.1002/qsar.200740123

Cited by 24 publications

(12 citation statements)

References 26 publications

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“…Similar systems have been reported in which furo [2,3-b]pyrazines are linked to the sugar moiety by means of a triazole bridge [62]. In this case Cu(I) has been produced in situ from Cu(0) and CuSO 4 , N,N,N-tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] amine (TBTA) has been used as the ligand for Cu(I).…”

Section: Nucleoside and Nucleotide Triazole Derivatives And Analoguesmentioning

confidence: 55%

Click Chemistry Under Microwave or Ultrasound Irradiation

Tagliapietra¹,

Binello²,

Cravotto

2011

COC

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The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is generally recognized as the most striking example of "click reaction". CuAAC fit so well into Sharpless' definition that it became almost synonymous with "click chemistry" itself. The most common catalyst systems employ Cu(II) salt in the presence of a reducing agent (i.e. sodium ascorbate) to generate the required Cu(I) catalyst in situ or as an alternative the comproportionation of Cu(II)/Cu(0) species. Although, Cu(I) catalyzes the reaction with a rate enhancement of 10 7 even in the absence of ligands and provides a clean and selective conversion to the 1,4-substituted triazoles, some bulky and scantily reactive substrates still require long reaction times and often few side products are formed. Outstanding results have been achieved by performing CuAAC under microwave (MW) irradiation. Several authors described excellent yields, high purity and short reaction times. In few cases also power ultrasound (US) accelerated the reaction, especially when heterogeneous catalysts or metallic copper are employed. The aim of this review is to summarize and highlight the huge advantages offered by MW-and US-promoted CuAAC. In the growing scenario of innovative synthetic strategies, we intend to emphasize the complementary role played by these non-conventional energy sources and click chemistry to achieve process intensification in organic synthesis.

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Section: Nucleoside and Nucleotide Triazole Derivatives And Analoguesmentioning

confidence: 55%

Click Chemistry Under Microwave or Ultrasound Irradiation

Tagliapietra¹,

Binello²,

Cravotto

2011

COC

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“…In the same manner, Ermolat’ev et al 14 (Scheme 6) and Broggi et al 15 (Scheme 7) showed that the Huisgen 1,3-cycloaddition can be completed in high yield in only few minutes using microwave irradiation.…”

Section: Nucleosidesmentioning

confidence: 84%

Cu(I)-Catalyzed Huisgen Azide−Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry

2009

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Introduction 4207 2. Nucleosides 4207 2.1. Base Modified Nucleosides 4207 2.2. Sugar Modified Nucleosides 4211 2.3. Nucleoside Bioconjugates 4214 3. Oligonucleotides 4216 3.1. 1,2,3-Triazole as Replacement of the Phosphodiester Linkage 4216 3.2. 1,2,3-Triazole as Linker for Solid Supported Synthesis 4217 3.3. Post-and Presynthetic DNA Modifications 4217 4. Conclusion 4219 5. Acknowledgments 4219 6. References 4219 Jong Hyun Cho was born in Gim-hae, South Korea, in 1967. In 2002, he received his Ph.D. in Organic Chemistry from Seoul National University (South Korea), working on biologically active peptide mimetics under the direction of Professor B. M. Kim. He then joined Professor Chung K.

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“…The same authors evaluated the coupling of a set of newly generated furo [2,3-b]pyrazines with five-membered sugars [88] using a microwave-assisted regioselective Cu I -catalysed [2+3] dipolar cycloaddition reaction. A small library of hitherto unknown nucleoside analogues was generated (Scheme 65).…”

Section: C-n Bond Formations By Click Chemistrymentioning

confidence: 99%

Recent Developments in Microwave‐Assisted, Transition‐Metal‐Catalysed C–C and C–N Bond‐Forming Reactions

2008

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A selective overview of the recent developments of microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions is presented. Microwave-assisted chemistry is a comparatively novel technique in the presentday synthetic world and has recently grown in an exponential manner, stretching from academia to a widely practiced technique in industry. Transition-metal-catalysed C-C and C-N bond-forming reactions represent one of the most interesting and well-investigated type of microwave-as-

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Synthesis of Furo[2,3‐b]pyrazine Nucleoside Analogues with 1,2,3‐Triazole Linkage

Cited by 24 publications

References 26 publications

Click Chemistry Under Microwave or Ultrasound Irradiation

Click Chemistry Under Microwave or Ultrasound Irradiation

Cu(I)-Catalyzed Huisgen Azide−Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry

Recent Developments in Microwave‐Assisted, Transition‐Metal‐Catalysed C–C and C–N Bond‐Forming Reactions

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