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α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion : Application towards the Synthesis of Rare Bicyclic Pyrazoles. / Chuprun, Sergey; Dar'In, Dmitry; Kantin, Grigory; Zhmurov, Petr; Krasavin, Mikhail.

In: Synlett, Vol. 31, No. 4, st-2019-b0609-l, 03.03.2020, p. 373-377.

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

Harvard

Chuprun, S, Dar'In, D, Kantin, G, Zhmurov, P & Krasavin, M 2020, 'α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles', Synlett, vol. 31, no. 4, st-2019-b0609-l, pp. 373-377. https://doi.org/10.1055/s-0039-1690047

APA

Chuprun, S., Dar'In, D., Kantin, G., Zhmurov, P., & Krasavin, M. (2020). α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles. Synlett, 31(4), 373-377. [st-2019-b0609-l]. https://doi.org/10.1055/s-0039-1690047

Vancouver

Chuprun S, Dar'In D, Kantin G, Zhmurov P, Krasavin M. α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles. Synlett. 2020 Mar 3;31(4):373-377. st-2019-b0609-l. https://doi.org/10.1055/s-0039-1690047

Author

Chuprun, Sergey ; Dar'In, Dmitry ; Kantin, Grigory ; Zhmurov, Petr ; Krasavin, Mikhail. / α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion : Application towards the Synthesis of Rare Bicyclic Pyrazoles. In: Synlett. 2020 ; Vol. 31, No. 4. pp. 373-377.

BibTeX

@article{080c217fad014a91a19b1e21cb803b54,
title = "α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles",
abstract = "A novel Sc(OTf) 3 -catalyzed Tiffeneau-Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson's reagent.",
keywords = "bicyclic pyrazoles, Lawesson's reagent, scandium triflate, Tiffeneau-Demjanov ring expansion, α-diazoacetamides, β-keto carboxamides, ENTRY, beta-keto carboxamides, CYCLOALKANONES, BIS-OXINDOLES, KETONES, alpha-diazoacetamides, COPPER-MEDIATED CONSTRUCTION, EFFICIENT, HOMOLOGATION, ACCESS, C-H",
author = "Sergey Chuprun and Dmitry Dar'In and Grigory Kantin and Petr Zhmurov and Mikhail Krasavin",
year = "2020",
month = mar,
day = "3",
doi = "10.1055/s-0039-1690047",
language = "English",
volume = "31",
pages = "373--377",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "4",

}

RIS

TY - JOUR

T1 - α-Diazoacetamides in Sc(OTf) 3 -Catalyzed Tiffeneau-Demjanov Ring Expansion

T2 - Application towards the Synthesis of Rare Bicyclic Pyrazoles

AU - Chuprun, Sergey

AU - Dar'In, Dmitry

AU - Kantin, Grigory

AU - Zhmurov, Petr

AU - Krasavin, Mikhail

PY - 2020/3/3

Y1 - 2020/3/3

N2 - A novel Sc(OTf) 3 -catalyzed Tiffeneau-Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson's reagent.

AB - A novel Sc(OTf) 3 -catalyzed Tiffeneau-Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson's reagent.

KW - bicyclic pyrazoles

KW - Lawesson's reagent

KW - scandium triflate

KW - Tiffeneau-Demjanov ring expansion

KW - α-diazoacetamides

KW - β-keto carboxamides

KW - ENTRY

KW - beta-keto carboxamides

KW - CYCLOALKANONES

KW - BIS-OXINDOLES

KW - KETONES

KW - alpha-diazoacetamides

KW - COPPER-MEDIATED CONSTRUCTION

KW - EFFICIENT

KW - HOMOLOGATION

KW - ACCESS

KW - C-H

UR - http://www.scopus.com/inward/record.url?scp=85079759135&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/28fef2f6-2e0f-3a4a-8a42-04ac91a661ad/

U2 - 10.1055/s-0039-1690047

DO - 10.1055/s-0039-1690047

M3 - Article

AN - SCOPUS:85079759135

VL - 31

SP - 373

EP - 377

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 4

M1 - st-2019-b0609-l

ER -

ID: 52203575