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Primary Vinyl Ethers as Acetylene Surrogate : A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis. / Ledovskaya, Maria S.; Voronin, Vladimir V.; Polynski, Mikhail V.; Lebedev, Andrey N.; Ananikov, Valentine P.

In: European Journal of Organic Chemistry, Vol. 2020, No. 29, 09.08.2020, p. 4571-4580.

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

Harvard

Ledovskaya, MS, Voronin, VV, Polynski, MV, Lebedev, AN & Ananikov, VP 2020, 'Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis', European Journal of Organic Chemistry, vol. 2020, no. 29, pp. 4571-4580. https://doi.org/10.1002/ejoc.202000674

APA

Ledovskaya, M. S., Voronin, V. V., Polynski, M. V., Lebedev, A. N., & Ananikov, V. P. (2020). Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis. European Journal of Organic Chemistry, 2020(29), 4571-4580. https://doi.org/10.1002/ejoc.202000674

Vancouver

Ledovskaya MS, Voronin VV, Polynski MV, Lebedev AN, Ananikov VP. Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis. European Journal of Organic Chemistry. 2020 Aug 9;2020(29):4571-4580. https://doi.org/10.1002/ejoc.202000674

Author

Ledovskaya, Maria S. ; Voronin, Vladimir V. ; Polynski, Mikhail V. ; Lebedev, Andrey N. ; Ananikov, Valentine P. / Primary Vinyl Ethers as Acetylene Surrogate : A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis. In: European Journal of Organic Chemistry. 2020 ; Vol. 2020, No. 29. pp. 4571-4580.

BibTeX

@article{678cff4401bf497a93fe00b9949601c0,
title = "Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis",
abstract = "A novel synthetic path to 1,3-disubstituted pyrazoles and their deuterated derivatives was developed. It is based on the reaction of vinyl ethers with hydrazonoyl chlorides in the presence of triethylamine. The reaction mechanism, clarified by the joint experimental and computational study, involves 1,3-dipolar cycloaddition of the in situ generated nitrile imines to vinyl ethers and subsequent cleavage of alcohol from the formed alkoxypyrazoline. The results highlight the possibility of using vinyl ethers as acetylene surrogate and provide a novel access to pyrazoles, 4,5-dideuteropyrazoles and their regioselectively labeled derivatives, 5-deuteropyrazoles.",
keywords = "Cycloaddition, Deuterium, Deuteropyrazole, Isotopic labeling, Vinyl ethers, AUXILIARY BASIS-SETS, HYDROXYLAMINE, ONE-POT SYNTHESIS, MOLECULAR-ORBITAL METHODS, THERMOCHEMISTRY, DRUG DISCOVERY, CALCIUM CARBIDE, NUCLEOPHILIC-ADDITION, REGIOSELECTIVITY, 1,3-DIPOLAR CYCLOADDITION",
author = "Ledovskaya, {Maria S.} and Voronin, {Vladimir V.} and Polynski, {Mikhail V.} and Lebedev, {Andrey N.} and Ananikov, {Valentine P.}",
note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2020",
month = aug,
day = "9",
doi = "10.1002/ejoc.202000674",
language = "English",
volume = "2020",
pages = "4571--4580",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "29",

}

RIS

TY - JOUR

T1 - Primary Vinyl Ethers as Acetylene Surrogate

T2 - A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis

AU - Ledovskaya, Maria S.

AU - Voronin, Vladimir V.

AU - Polynski, Mikhail V.

AU - Lebedev, Andrey N.

AU - Ananikov, Valentine P.

N1 - Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/8/9

Y1 - 2020/8/9

N2 - A novel synthetic path to 1,3-disubstituted pyrazoles and their deuterated derivatives was developed. It is based on the reaction of vinyl ethers with hydrazonoyl chlorides in the presence of triethylamine. The reaction mechanism, clarified by the joint experimental and computational study, involves 1,3-dipolar cycloaddition of the in situ generated nitrile imines to vinyl ethers and subsequent cleavage of alcohol from the formed alkoxypyrazoline. The results highlight the possibility of using vinyl ethers as acetylene surrogate and provide a novel access to pyrazoles, 4,5-dideuteropyrazoles and their regioselectively labeled derivatives, 5-deuteropyrazoles.

AB - A novel synthetic path to 1,3-disubstituted pyrazoles and their deuterated derivatives was developed. It is based on the reaction of vinyl ethers with hydrazonoyl chlorides in the presence of triethylamine. The reaction mechanism, clarified by the joint experimental and computational study, involves 1,3-dipolar cycloaddition of the in situ generated nitrile imines to vinyl ethers and subsequent cleavage of alcohol from the formed alkoxypyrazoline. The results highlight the possibility of using vinyl ethers as acetylene surrogate and provide a novel access to pyrazoles, 4,5-dideuteropyrazoles and their regioselectively labeled derivatives, 5-deuteropyrazoles.

KW - Cycloaddition

KW - Deuterium

KW - Deuteropyrazole

KW - Isotopic labeling

KW - Vinyl ethers

KW - AUXILIARY BASIS-SETS

KW - HYDROXYLAMINE

KW - ONE-POT SYNTHESIS

KW - MOLECULAR-ORBITAL METHODS

KW - THERMOCHEMISTRY

KW - DRUG DISCOVERY

KW - CALCIUM CARBIDE

KW - NUCLEOPHILIC-ADDITION

KW - REGIOSELECTIVITY

KW - 1,3-DIPOLAR CYCLOADDITION

UR - http://www.scopus.com/inward/record.url?scp=85088120457&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/23802b10-5d0a-36b1-99a0-a0cfe21a39f4/

U2 - 10.1002/ejoc.202000674

DO - 10.1002/ejoc.202000674

M3 - Article

AN - SCOPUS:85088120457

VL - 2020

SP - 4571

EP - 4580

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 29

ER -

ID: 61006485