Organic and Biomolecular Chemistry, volume 5, issue 11, pages 1695

Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction

Yi Xia ^{1, 2}

Wei Li ¹

Fanqi Qu ¹

Zhijin Fan ³

Xiufeng Liu ³

Charles Berro ²

Evelyne Rauzy ²

Ling Peng ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, P. R. China |

CNRS UMR 6114, Département de chimie, 163, avenue de Luminy, Marseille, France |

State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, P. R. China |

Publication type: Journal Article

Publication date: 2007-04-25

Royal Society of Chemistry (RSC)

Journal: Organic and Biomolecular Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 3.2

ISSN: 14770520, 14770539

DOI: 10.1039/b703420b

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Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Novel bitriazolyl nucleosides were synthesized via the Huisgen reaction, starting with 3-azidotriazole nucleoside (1). Surprisingly, its isomer, 5-azidotriazole nucleoside (1') did not yield the corresponding Huisgen reaction products efficiently because it was rapidly reduced to amine in the presence of Cu(II)-ascorbate. The significant differences between the reactivity of these two isomers in Cu(II)-ascorbate mediated reactions are mainly due to differences in their electronic properties and steric congestion as a result of different relative positions of the azido and the ribosyl moieties.

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Citations by journals

	1 2 3 4 5 6 7
Bioorganic and Medicinal Chemistry Letters	Bioorganic and Medicinal Chemistry Letters, 7, 11.86% Bioorganic and Medicinal Chemistry Letters 7 publications, 11.86%
Tetrahedron Letters	Tetrahedron Letters, 5, 8.47% Tetrahedron Letters 5 publications, 8.47%
European Journal of Medicinal Chemistry	European Journal of Medicinal Chemistry, 4, 6.78% European Journal of Medicinal Chemistry 4 publications, 6.78%
Chemistry - A European Journal	Chemistry - A European Journal, 3, 5.08% Chemistry - A European Journal 3 publications, 5.08%
Journal of Medicinal Chemistry	Journal of Medicinal Chemistry, 3, 5.08% Journal of Medicinal Chemistry 3 publications, 5.08%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 3, 5.08% Organic and Biomolecular Chemistry 3 publications, 5.08%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 2, 3.39% Chemistry of Heterocyclic Compounds 2 publications, 3.39%
Tetrahedron	Tetrahedron, 2, 3.39% Tetrahedron 2 publications, 3.39%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 2, 3.39% Advanced Synthesis and Catalysis 2 publications, 3.39%
Chemical Reviews	Chemical Reviews, 2, 3.39% Chemical Reviews 2 publications, 3.39%
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 3.39% Journal of Organic Chemistry 2 publications, 3.39%
Journal of the American Chemical Society	Journal of the American Chemical Society, 2, 3.39% Journal of the American Chemical Society 2 publications, 3.39%
Journal of Fluorine Chemistry	Journal of Fluorine Chemistry, 1, 1.69% Journal of Fluorine Chemistry 1 publication, 1.69%
Journal of Molecular Modeling	Journal of Molecular Modeling, 1, 1.69% Journal of Molecular Modeling 1 publication, 1.69%
Journal of Solution Chemistry	Journal of Solution Chemistry, 1, 1.69% Journal of Solution Chemistry 1 publication, 1.69%
Cancer Letters	Cancer Letters, 1, 1.69% Cancer Letters 1 publication, 1.69%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 1, 1.69% Bioorganic and Medicinal Chemistry 1 publication, 1.69%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 1.69% Asian Journal of Organic Chemistry 1 publication, 1.69%
ChemInform	ChemInform, 1, 1.69% ChemInform 1 publication, 1.69%
Helvetica Chimica Acta	Helvetica Chimica Acta, 1, 1.69% Helvetica Chimica Acta 1 publication, 1.69%
Journal of Physical Organic Chemistry	Journal of Physical Organic Chemistry, 1, 1.69% Journal of Physical Organic Chemistry 1 publication, 1.69%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 1.69% European Journal of Organic Chemistry 1 publication, 1.69%
Inorganic Chemistry	Inorganic Chemistry, 1, 1.69% Inorganic Chemistry 1 publication, 1.69%
Organic Letters	Organic Letters, 1, 1.69% Organic Letters 1 publication, 1.69%
New Journal of Chemistry	New Journal of Chemistry, 1, 1.69% New Journal of Chemistry 1 publication, 1.69%
Chemical Science	Chemical Science, 1, 1.69% Chemical Science 1 publication, 1.69%
Catalysis Science and Technology	Catalysis Science and Technology, 1, 1.69% Catalysis Science and Technology 1 publication, 1.69%
Natural Product Reports	Natural Product Reports, 1, 1.69% Natural Product Reports 1 publication, 1.69%
Nucleosides, Nucleotides and Nucleic Acids	Nucleosides, Nucleotides and Nucleic Acids, 1, 1.69% Nucleosides, Nucleotides and Nucleic Acids 1 publication, 1.69%
	1 2 3 4 5 6 7

Citations by publishers

	5 10 15 20 25
Elsevier	Elsevier, 22, 37.29% Elsevier 22 publications, 37.29%
American Chemical Society (ACS)	American Chemical Society (ACS), 11, 18.64% American Chemical Society (ACS) 11 publications, 18.64%
Wiley	Wiley, 10, 16.95% Wiley 10 publications, 16.95%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 7, 11.86% Royal Society of Chemistry (RSC) 7 publications, 11.86%
Springer Nature	Springer Nature, 4, 6.78% Springer Nature 4 publications, 6.78%
Taylor & Francis	Taylor & Francis, 1, 1.69% Taylor & Francis 1 publication, 1.69%
RTU MIREA	RTU MIREA, 1, 1.69% RTU MIREA 1 publication, 1.69%
Bentham Science	Bentham Science, 1, 1.69% Bentham Science 1 publication, 1.69%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.69% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.69%
	5 10 15 20 25

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Xia Y. et al. Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction // Organic and Biomolecular Chemistry. 2007. Vol. 5. No. 11. p. 1695.

GOST all authors (up to 50) Copy

Xia Y., Li W., Qu F., Fan Z., Liu X., Berro C., Rauzy E., Peng L. Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction // Organic and Biomolecular Chemistry. 2007. Vol. 5. No. 11. p. 1695.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/b703420b

UR - https://doi.org/10.1039/b703420b

TI - Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction

T2 - Organic and Biomolecular Chemistry

AU - Qu, Fanqi

AU - Fan, Zhijin

AU - Liu, Xiufeng

AU - Berro, Charles

AU - Rauzy, Evelyne

AU - Xia, Yi

AU - Li, Wei

AU - Peng, Ling

PY - 2007

DA - 2007/04/25 00:00:00

PB - Royal Society of Chemistry (RSC)

SP - 1695

IS - 11

VL - 5

SN - 1477-0520

SN - 1477-0539

ER -

BibTex |

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BibTex Copy

@article{2007_Xia,

author = {Fanqi Qu and Zhijin Fan and Xiufeng Liu and Charles Berro and Evelyne Rauzy and Yi Xia and Wei Li and Ling Peng},

title = {Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction},

journal = {Organic and Biomolecular Chemistry},

year = {2007},

volume = {5},

publisher = {Royal Society of Chemistry (RSC)},

month = {apr},

url = {https://doi.org/10.1039/b703420b},

number = {11},

pages = {1695},

doi = {10.1039/b703420b}

}

MLA

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MLA Copy

Xia, Yi, et al. “Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction.” Organic and Biomolecular Chemistry, vol. 5, no. 11, Apr. 2007, p. 1695. https://doi.org/10.1039/b703420b.

Found error?

Publisher

Royal Society of Chemistry (RSC)

Journal

Organic and Biomolecular Chemistry

Quartile SCImago

Quartile WOS

Impact factor

3.2

ISSN

14770520 (Print)
14770539 (Electronic)

Profiles

Peng, Ling Ling