Organic and Biomolecular Chemistry

, volume 18 , issue 7 , pages 1436-1448

Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines

Vladimir A Motornov ^{1, 2, 3, 4, 5, 6, 7}

Andrey A Tabolin ^{1, 3, 4, 5, 6}

Yulia V. Nelyubina ^{4, 5, 6, 8, 9}

Valentine G. Nenajdenko ^{6, 10, 11, 12, 13}

Sema L. Ioffe ^{1, 3, 4, 5, 6}

Hide authors affiliations Show authors affiliations: 13 affiliations

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, Russia |

Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow, 125047, Russia |

N. D. Zelinsky Institute of Organic Chemistry |

⁴

RUSSIAN ACADEMY OF SCIENCES

⁵

Moscow

⁶

Russia |

⁷

Higher Chemical College

⁸

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, Russia |

⁹

A. N. Nesmeyanov Institute of Organoelement Compounds |

¹⁰

Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow, 119991, Russia |

¹¹

DEPARTMENT OF CHEMISTRY

¹²

M. V. Lomonosov Moscow State University |

¹³

Moscow, 119991

Publication type: Journal Article

Publication date: 2020-01-24

Royal Society of Chemistry (RSC)

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR: 0.600

CiteScore: 5.2

Impact factor: 2.7

ISSN: 14770520, 14770539

DOI: 10.1039/C9OB02668A

Copy DOI

PubMed ID: 32022079

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

An efficient route to pyrazolo[1,5-a]pyridines by Cu(OAc)2-promoted oxidative [3 + 2]-annulation of nitroalkenes with in situ generated pyridinium imines is developed. The reaction with α-fluoronitroalkenes enables the first preparative synthesis of 3-fluoro-pyrazolo[1,5-a]pyridines. Cycloaddition with α-unsubstituted nitroalkenes provides access to 3-nitro-pyrazolo[1,5-a]pyridines in excellent yields. A broad transformation scope was demonstrated. Both electron-rich and electron-deficient nitroalkenes as well as different aminopyridinium salts can be used for the assembly of the target pyrazolo[1,5-a]pyridines. The related aza-heterocycles, namely, pyrazolo[1,5-a]pyrazines and pyrazolo[1,5-b]pyridazines, were successfully prepared via the present methodology. The possible mechanism of the reaction is discussed.

Found

2 citations

Nelyubina Yulia

🤝

DSc in Chemistry

506 publications, 7 606 citations, 1 review

h-index: 38

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

Metal-organic frameworks

Quantum technologies

Sensors

2 citations

Aksenov Aleksandr

🥼 🤝

DSc in Chemistry, professor

245 publications, 2 202 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Izmest'ev Alexei

PhD in Chemistry

33 publications, 306 citations

h-index: 12

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Vinogradov Dmitry

PhD in Chemistry

10 publications, 50 citations

h-index: 5

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 743 citations

h-index: 30

Ural Federal University

1 citation

Arutiunov Nikolai

PhD in Chemistry, senior lecturer

29 publications, 233 citations

h-index: 9

North Caucasus Federal University

1 citation

Ivleva Elena

67 publications, 470 citations

h-index: 12

Samara State Technical University

Research interests

Organic Chemistry

Organic synthesis

Top-30

Journals

	1 2 3 4 5
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 5, 12.5% Organic and Biomolecular Chemistry 5 publications, 12.5%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 3, 7.5% Organic Chemistry Frontiers 3 publications, 7.5%
Organic Reaction Mechanisms	Organic Reaction Mechanisms, 3, 7.5% Organic Reaction Mechanisms 3 publications, 7.5%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 2, 5% European Journal of Organic Chemistry 2 publications, 5%
Molecules	Molecules, 2, 5% Molecules 2 publications, 5%
Organic Letters	Organic Letters, 2, 5% Organic Letters 2 publications, 5%
New Journal of Chemistry	New Journal of Chemistry, 2, 5% New Journal of Chemistry 2 publications, 5%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 2, 5% Progress in Heterocyclic Chemistry 2 publications, 5%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 2, 5% Advanced Synthesis and Catalysis 2 publications, 5%
Chemical Communications	Chemical Communications, 2, 5% Chemical Communications 2 publications, 5%
Beilstein Journal of Organic Chemistry	Beilstein Journal of Organic Chemistry, 1, 2.5% Beilstein Journal of Organic Chemistry 1 publication, 2.5%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 2.5% Chemistry of Heterocyclic Compounds 1 publication, 2.5%
Chinese Chemical Letters	Chinese Chemical Letters, 1, 2.5% Chinese Chemical Letters 1 publication, 2.5%
ChemistrySelect	ChemistrySelect, 1, 2.5% ChemistrySelect 1 publication, 2.5%
Chinese Journal of Chemistry	Chinese Journal of Chemistry, 1, 2.5% Chinese Journal of Chemistry 1 publication, 2.5%
Synthetic Communications	Synthetic Communications, 1, 2.5% Synthetic Communications 1 publication, 2.5%
Advances in Heterocyclic Chemistry	Advances in Heterocyclic Chemistry, 1, 2.5% Advances in Heterocyclic Chemistry 1 publication, 2.5%
Letters in Drug Design and Discovery	Letters in Drug Design and Discovery, 1, 2.5% Letters in Drug Design and Discovery 1 publication, 2.5%
Synlett	Synlett, 1, 2.5% Synlett 1 publication, 2.5%
Journal of Heterocyclic Chemistry	Journal of Heterocyclic Chemistry, 1, 2.5% Journal of Heterocyclic Chemistry 1 publication, 2.5%
ChemPhotoChem	ChemPhotoChem, 1, 2.5% ChemPhotoChem 1 publication, 2.5%
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 1, 2.5% Russian Journal of Organic Chemistry 1 publication, 2.5%
Журнал органической химии	Журнал органической химии, 1, 2.5% Журнал органической химии 1 publication, 2.5%
Russian Chemical Bulletin	Russian Chemical Bulletin, 1, 2.5% Russian Chemical Bulletin 1 publication, 2.5%
	1 2 3 4 5

Publishers

	2 4 6 8 10 12
Wiley	Wiley, 12, 30% Wiley 12 publications, 30%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 12, 30% Royal Society of Chemistry (RSC) 12 publications, 30%
Elsevier	Elsevier, 4, 10% Elsevier 4 publications, 10%
MDPI	MDPI, 2, 5% MDPI 2 publications, 5%
Springer Nature	Springer Nature, 2, 5% Springer Nature 2 publications, 5%
American Chemical Society (ACS)	American Chemical Society (ACS), 2, 5% American Chemical Society (ACS) 2 publications, 5%
Beilstein-Institut	Beilstein-Institut, 1, 2.5% Beilstein-Institut 1 publication, 2.5%
Taylor & Francis	Taylor & Francis, 1, 2.5% Taylor & Francis 1 publication, 2.5%
Bentham Science Publishers Ltd.	Bentham Science Publishers Ltd., 1, 2.5% Bentham Science Publishers Ltd. 1 publication, 2.5%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 2.5% Georg Thieme Verlag KG 1 publication, 2.5%
Pleiades Publishing	Pleiades Publishing, 1, 2.5% Pleiades Publishing 1 publication, 2.5%
The Russian Academy of Sciences	The Russian Academy of Sciences, 1, 2.5% The Russian Academy of Sciences 1 publication, 2.5%
	2 4 6 8 10 12

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Motornov V. A. et al. Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 7. pp. 1436-1448.

GOST all authors (up to 50) Copy

Motornov V. A., Tabolin A. A., Nelyubina Y. V., Nenajdenko V. G., Ioffe S. L. Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 7. pp. 1436-1448.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/C9OB02668A

UR - https://xlink.rsc.org/?DOI=C9OB02668A

TI - Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines

T2 - Organic and Biomolecular Chemistry

AU - Motornov, Vladimir A

AU - Tabolin, Andrey A

AU - Nelyubina, Yulia V.

AU - Nenajdenko, Valentine G.

AU - Ioffe, Sema L.

PY - 2020

DA - 2020/01/24

PB - Royal Society of Chemistry (RSC)

SP - 1436-1448

IS - 7

VL - 18

PMID - 32022079

SN - 1477-0520

SN - 1477-0539

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2020_Motornov,

author = {Vladimir A Motornov and Andrey A Tabolin and Yulia V. Nelyubina and Valentine G. Nenajdenko and Sema L. Ioffe},

title = {Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines},

journal = {Organic and Biomolecular Chemistry},

year = {2020},

volume = {18},

publisher = {Royal Society of Chemistry (RSC)},

month = {jan},

url = {https://xlink.rsc.org/?DOI=C9OB02668A},

number = {7},

pages = {1436--1448},

doi = {10.1039/C9OB02668A}

}

MLA

Cite this

MLA Copy

Motornov, Vladimir A., et al. “Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines.” Organic and Biomolecular Chemistry, vol. 18, no. 7, Jan. 2020, pp. 1436-1448. https://xlink.rsc.org/?DOI=C9OB02668A.

Publisher

Royal Society of Chemistry (RSC)

Journal

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR

0.600

CiteScore

5.2

Impact factor

2.7

ISSN

14770520 (Print)

14770539 (Electronic)

Labs

Molecular Structure Research Center

Profiles