A highly efficient microwave-assisted solvent-free synthesis of α- and β-2′-deoxy-1,2,3-triazolyl-nucleosides

Guezguez, Raja; Bougrin, Khalid; Akri, Khalid El; Benhida, Rachid

doi:10.1016/j.tetlet.2006.05.050

Cited by 74 publications

(29 citation statements)

References 20 publications

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“…Upon excitation, the normal excited molecules (N *) may undergo the ESIPT reaction producing the tautomer (T *) excited form. Both states are highly emissive, the T* band being in general red-shifted comparing to the N * band, as reported for triazolyl-and thienyl-hydroxychromones (Scheme 20) [100][101][102]. 3,4-Dihydro-α-lapachone (90), and its isomer 3,4-dihydro-β-lapachone (91) are the most important members of the dihydrochromene derivatives coupled with ortho-and para-quinones.…”

Section: Benzopyrones: Coumarins and Chromonesmentioning

confidence: 57%

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

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This review describes the formation of six-membered heterocyclic compounds and their fused analogues under microwave activation using modern organic transformations including cyclocondensation, cycloaddition, multicomponents and other modular reactions. The review is divided according to the main heterocycle types in order of increasing complexity, starting with heterocyclic systems containing one, two and three heteroatoms and their fused analogues. Recent microwave applications are reviewed, with special focus on the chemistry of bioactive compounds. Selected examples from the 2006 to 2015 literature are discussed.

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Section: Benzopyrones: Coumarins and Chromonesmentioning

confidence: 57%

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

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“…It was found that the chromatographic separation of the a-and b-anomers is best performed for DMTr derivatives of the triazolyl nucleoside due to the noticeable difference in The configuration of the triazolyl nucleoside at C(1') was unambiguously determined by ROESY experiments for derivative 5. 2D-ROESY Spectrum displayed a strong HÀC(1')/HÀC(4') correlation, consistent with the b-configuration at the glycosidic bond [2]. Additionally, analysis of the correlations between the H-atoms at C(3'), C(2'), and C(1') confirms b-configuration of the nucleoside.…”

mentioning

confidence: 53%

“…In addition, for a short aminoalkyl arm, it would be possible to place the group of interest inside the helical structure. This possibility is important for applications based on the intercalation and stacking interactions [19] [20].In a recent study, a number of substituted 1,2,3-triazolyl nucleosides have been synthesized by the Huisgen reaction [2]. The synthesis of aminoalkyl derivatives by this method, however, has not been reported.…”

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confidence: 99%

Simple and Stereoselective Preparation of an 4‐(Aminomethyl)‐1,2,3‐triazolyl Nucleoside Phosphoramidite

Kolganova

Florentiev

Чудинов

et al. 2011

Chemistry & Biodiversity

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A simple and stereoselective synthesis of a protected 4-(aminomethyl)-1-(2-deoxy-β-D-ribofuranosyl)-1,2,3-triazole cyanoethyl phosphoramidite was developed for the modification of synthetic oligonucleotides. The configuration of the 1,2,3-triazolyl moiety with respect to the deoxyribose was unambiguously determined in ROESY experiments. The aminomethyl group of the triazolyl nucleotide was fully functional in labelling reactions. Furthermore, the hybridization behavior of 5' triazole-terminated oligonucleotide was similar to that of 5' aminohexyl-terminated oligomer with the same sequence. Internal modifications of the oligonucleotide strands resulted in significant decrease of duplex stability.

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“…Selected examples of this synthetic methodology starting with the β-azido-2-deoxyribose 150 are presented in Scheme 53. [110] Scheme 54.…”

Section: Cycloadditions Of Azidesmentioning

confidence: 99%

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Piñeiro

Melo

2009

Eur J Org Chem

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The review describes the use of microwave technology to carry out 1,3-dipolar cycloaddition reactions, an important tool for the construction of five-membered heterocycles. Microwave methodology can be applied to generate 1,3-dipoles (nitrones, nitrile oxides, azomethine ylides, azomethine imines, nitrile imines, azides, carbonyl ylides) and to promote the subsequent cycloaddition and usually avoids harsh reaction conditions. This nonconventional energy source is able

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A highly efficient microwave-assisted solvent-free synthesis of α- and β-2′-deoxy-1,2,3-triazolyl-nucleosides

Cited by 74 publications

References 20 publications

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

Simple and Stereoselective Preparation of an 4‐(Aminomethyl)‐1,2,3‐triazolyl Nucleoside Phosphoramidite

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

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