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α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines. / Safrygin, Alexander; Dar'in, Dmitry; Kantin, Grigory; Krasavin, Mikhail.

In: European Journal of Organic Chemistry, Vol. 2019, No. 29, 07.08.2019, p. 4721-4724.

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

Harvard

Safrygin, A, Dar'in, D, Kantin, G & Krasavin, M 2019, 'α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines', European Journal of Organic Chemistry, vol. 2019, no. 29, pp. 4721-4724. https://doi.org/10.1002/ejoc.201900698

APA

Safrygin, A., Dar'in, D., Kantin, G., & Krasavin, M. (2019). α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines. European Journal of Organic Chemistry, 2019(29), 4721-4724. https://doi.org/10.1002/ejoc.201900698

Vancouver

Safrygin A, Dar'in D, Kantin G, Krasavin M. α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines. European Journal of Organic Chemistry. 2019 Aug 7;2019(29):4721-4724. https://doi.org/10.1002/ejoc.201900698

Author

Safrygin, Alexander ; Dar'in, Dmitry ; Kantin, Grigory ; Krasavin, Mikhail. / α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 29. pp. 4721-4724.

BibTeX

@article{4348395cabc543e09c364dbd367ac0d4,
title = "α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines",
abstract = "The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.",
keywords = "Triazoles, Wolff cyclocondensation, Wolff rearrangement, α-Diazo-β-oxosulfones, α-Sulfonyl acetanilides, alpha-Sulfonyl acetanilides, alpha-Diazo-beta-oxosulfones, CYCLOCONDENSATION",
author = "Alexander Safrygin and Dmitry Dar'in and Grigory Kantin and Mikhail Krasavin",
year = "2019",
month = aug,
day = "7",
doi = "10.1002/ejoc.201900698",
language = "English",
volume = "2019",
pages = "4721--4724",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "29",

}

RIS

TY - JOUR

T1 - α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines

AU - Safrygin, Alexander

AU - Dar'in, Dmitry

AU - Kantin, Grigory

AU - Krasavin, Mikhail

PY - 2019/8/7

Y1 - 2019/8/7

N2 - The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.

AB - The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.

KW - Triazoles

KW - Wolff cyclocondensation

KW - Wolff rearrangement

KW - α-Diazo-β-oxosulfones

KW - α-Sulfonyl acetanilides

KW - alpha-Sulfonyl acetanilides

KW - alpha-Diazo-beta-oxosulfones

KW - CYCLOCONDENSATION

UR - http://www.scopus.com/inward/record.url?scp=85069850997&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201900698

DO - 10.1002/ejoc.201900698

M3 - Article

AN - SCOPUS:85069850997

VL - 2019

SP - 4721

EP - 4724

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 29

ER -

ID: 46203920