Journal of Organic Chemistry

, том 84 , издание 4 , страницы 1925-1940

1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles

Тип публикации: Journal Article

Дата публикации: 2019-01-11

American Chemical Society (ACS)

Journal of Organic Chemistry

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wos Q1

white level БС1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.8b02916

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PubMed ID: 30632741

Organic Chemistry

Краткое описание

Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris(triphenylphosphine)copper(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.

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Govdi A. I. et al. 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles // Journal of Organic Chemistry. 2019. Vol. 84. No. 4. pp. 1925-1940.

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Govdi A. I., Danilkina N. A., Ponomarev A. V., Balova I. A. 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles // Journal of Organic Chemistry. 2019. Vol. 84. No. 4. pp. 1925-1940.

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TY - JOUR

DO - 10.1021/acs.joc.8b02916

UR - https://doi.org/10.1021/acs.joc.8b02916

TI - 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles

T2 - Journal of Organic Chemistry

AU - Govdi, Anastasia I

AU - Danilkina, Natalia A

AU - Ponomarev, Alexander V

AU - Balova, Irina A.

PY - 2019

DA - 2019/01/11

PB - American Chemical Society (ACS)

SP - 1925-1940

IS - 4

VL - 84

PMID - 30632741

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2019_Govdi,

author = {Anastasia I Govdi and Natalia A Danilkina and Alexander V Ponomarev and Irina A. Balova},

title = {1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {jan},

url = {https://doi.org/10.1021/acs.joc.8b02916},

number = {4},

pages = {1925--1940},

doi = {10.1021/acs.joc.8b02916}

}

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Govdi, Anastasia I., et al. “1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles.” Journal of Organic Chemistry, vol. 84, no. 4, Jan. 2019, pp. 1925-1940. https://doi.org/10.1021/acs.joc.8b02916.