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Diazo Glutaconimides : an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones. / Guranova, Natalia; Kantin, Grigory; Dar'in, Dmitry; Krasavin, Mikhail.

In: European Journal of Organic Chemistry, Vol. 2021, No. 4, 26.01.2021, p. 623 - 631.

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

Harvard

Guranova, N, Kantin, G, Dar'in, D & Krasavin, M 2021, 'Diazo Glutaconimides: an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones', European Journal of Organic Chemistry, vol. 2021, no. 4, pp. 623 - 631. https://doi.org/10.1002/ejoc.202001451

APA

Guranova, N., Kantin, G., Dar'in, D., & Krasavin, M. (2021). Diazo Glutaconimides: an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones. European Journal of Organic Chemistry, 2021(4), 623 - 631. https://doi.org/10.1002/ejoc.202001451

Vancouver

Guranova N, Kantin G, Dar'in D, Krasavin M. Diazo Glutaconimides: an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones. European Journal of Organic Chemistry. 2021 Jan 26;2021(4):623 - 631. https://doi.org/10.1002/ejoc.202001451

Author

Guranova, Natalia ; Kantin, Grigory ; Dar'in, Dmitry ; Krasavin, Mikhail. / Diazo Glutaconimides : an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones. In: European Journal of Organic Chemistry. 2021 ; Vol. 2021, No. 4. pp. 623 - 631.

BibTeX

@article{3c8bf1d5ef3746a8a8fc609c3efd461d,
title = "Diazo Glutaconimides: an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones",
abstract = "A convenient general approach towards 1,4-disubstituted α-diazo glutaconimides starting from β-substituted glutaconic acid anhydrides has been developed. It involves condensation with amines and subsequent diazo transfer reaction. This new class of diazocarbonyl heterocycles has been converted into a series of polysubstituted pyridine-2,6(1H,3H)-diones and oxazolo[5,4-b]pyridin-5(4H)-ones via a Rh2(esp)2-catalyzed XH-insertion reaction and [3+2] cycloaddition with nitriles, respectively.",
keywords = "Diazo glutaconimides, Diazo transfer, Oxazolo[5,4-b]pyridines, Rh(II) catalysis, [3+2] Cycloaddition",
author = "Natalia Guranova and Grigory Kantin and Dmitry Dar'in and Mikhail Krasavin",
note = "Funding Information: This research was supported by the Russian Science Foundation (project grant 20‐13‐00024). We thank the Research Center for Magnetic Resonance and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University Research Park for obtaining the analytical data. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2021",
month = jan,
day = "26",
doi = "10.1002/ejoc.202001451",
language = "English",
volume = "2021",
pages = "623 -- 631",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "4",

}

RIS

TY - JOUR

T1 - Diazo Glutaconimides

T2 - an Unexplored Type of Heterocyclic α-Diazocarbonyl Compounds Conveniently Evolved into Pyridine-2,6(1H,3H)-diones and Oxazolo[5,4-b]pyridin-5(4H)-ones

AU - Guranova, Natalia

AU - Kantin, Grigory

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

N1 - Funding Information: This research was supported by the Russian Science Foundation (project grant 20‐13‐00024). We thank the Research Center for Magnetic Resonance and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University Research Park for obtaining the analytical data. Publisher Copyright: © 2020 Wiley-VCH GmbH Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2021/1/26

Y1 - 2021/1/26

N2 - A convenient general approach towards 1,4-disubstituted α-diazo glutaconimides starting from β-substituted glutaconic acid anhydrides has been developed. It involves condensation with amines and subsequent diazo transfer reaction. This new class of diazocarbonyl heterocycles has been converted into a series of polysubstituted pyridine-2,6(1H,3H)-diones and oxazolo[5,4-b]pyridin-5(4H)-ones via a Rh2(esp)2-catalyzed XH-insertion reaction and [3+2] cycloaddition with nitriles, respectively.

AB - A convenient general approach towards 1,4-disubstituted α-diazo glutaconimides starting from β-substituted glutaconic acid anhydrides has been developed. It involves condensation with amines and subsequent diazo transfer reaction. This new class of diazocarbonyl heterocycles has been converted into a series of polysubstituted pyridine-2,6(1H,3H)-diones and oxazolo[5,4-b]pyridin-5(4H)-ones via a Rh2(esp)2-catalyzed XH-insertion reaction and [3+2] cycloaddition with nitriles, respectively.

KW - Diazo glutaconimides

KW - Diazo transfer

KW - Oxazolo[5,4-b]pyridines

KW - Rh(II) catalysis

KW - [3+2] Cycloaddition

UR - http://www.scopus.com/inward/record.url?scp=85097938689&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/9bae8e7a-fad8-36ed-8a2e-f70364d8a9ba/

U2 - 10.1002/ejoc.202001451

DO - 10.1002/ejoc.202001451

M3 - Article

AN - SCOPUS:85097938689

VL - 2021

SP - 623

EP - 631

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 4

ER -

ID: 72052994