Cycloaddition Reactions of In Situ Generated C2D2 in Dioxane: Efficient Synthetic Approach to D2-Labeled Nitrogen Heterocycles

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Cycloaddition Reactions of In Situ Generated C2D2 in Dioxane: Efficient Synthetic Approach to D2-Labeled Nitrogen Heterocycles. / Voronin, Vladimir ; Ledovskaya, Maria ; Rodygin, Konstantin; Ananikov, Valentine P.

In: European Journal of Organic Chemistry, Vol. 2021, No. 41, 08.11.2021, p. 5640-5648.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{a3c2378be91a46328972189d6d372db0,

title = "Cycloaddition Reactions of In Situ Generated C2D2 in Dioxane: Efficient Synthetic Approach to D2-Labeled Nitrogen Heterocycles",

abstract = "In this work, a universal synthetic approach to the synthesis of D2-labeled nitrogen heterocycles based on cycloaddition reactions of in situ generated dideuteroacetylene is reported. A key feature of the developed method is the use of dioxane as a deuterium-exchange-proof solvent, which allowed dideuterosubstituted heterocycles to be obtained in up to 99% deuteration. The developed method was demonstrated to be suitable for the synthesis of D2-labeled triazoles, isoxazoles, pyrazoles and pyridazines.",

keywords = "Calcium carbide, Click chemistry, Cycloaddition, Labeling, Nitrogen heterocycles, Calcium carbide, Click chemistry, Cycloaddition, Labeling, Nitrogen heterocycles, H/D EXCHANGE, ACIDS, ALKENE HYDROGENATION, COMPLEXES, DEUTERIUM, DISCOVERY, AMINES, DEUTERATION, CHLORIDES, CATALYSTS",

author = "Vladimir Voronin and Maria Ledovskaya and Konstantin Rodygin and Ananikov, {Valentine P.}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = nov,

day = "8",

doi = "10.1002/ejoc.202101085",

language = "English",

volume = "2021",

pages = "5640--5648",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "41",

}

RIS

TY - JOUR

T1 - Cycloaddition Reactions of In Situ Generated C2D2 in Dioxane: Efficient Synthetic Approach to D2-Labeled Nitrogen Heterocycles

AU - Voronin, Vladimir

AU - Ledovskaya, Maria

AU - Rodygin, Konstantin

AU - Ananikov, Valentine P.

PY - 2021/11/8

Y1 - 2021/11/8

N2 - In this work, a universal synthetic approach to the synthesis of D2-labeled nitrogen heterocycles based on cycloaddition reactions of in situ generated dideuteroacetylene is reported. A key feature of the developed method is the use of dioxane as a deuterium-exchange-proof solvent, which allowed dideuterosubstituted heterocycles to be obtained in up to 99% deuteration. The developed method was demonstrated to be suitable for the synthesis of D2-labeled triazoles, isoxazoles, pyrazoles and pyridazines.

AB - In this work, a universal synthetic approach to the synthesis of D2-labeled nitrogen heterocycles based on cycloaddition reactions of in situ generated dideuteroacetylene is reported. A key feature of the developed method is the use of dioxane as a deuterium-exchange-proof solvent, which allowed dideuterosubstituted heterocycles to be obtained in up to 99% deuteration. The developed method was demonstrated to be suitable for the synthesis of D2-labeled triazoles, isoxazoles, pyrazoles and pyridazines.

KW - Calcium carbide

KW - Click chemistry

KW - Cycloaddition

KW - Labeling

KW - Nitrogen heterocycles

KW - Calcium carbide

KW - Click chemistry

KW - Cycloaddition

KW - Labeling

KW - Nitrogen heterocycles

KW - H/D EXCHANGE

KW - ACIDS

KW - ALKENE HYDROGENATION

KW - COMPLEXES

KW - DEUTERIUM

KW - DISCOVERY

KW - AMINES

KW - DEUTERATION

KW - CHLORIDES

KW - CATALYSTS

UR - http://www.scopus.com/inward/record.url?scp=85118540271&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/97f6b054-bb7a-33f1-b877-9712553dd728/

U2 - 10.1002/ejoc.202101085

DO - 10.1002/ejoc.202101085

M3 - Article

VL - 2021

SP - 5640

EP - 5648

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 41

ER -

ID: 87541644