European Journal of Organic Chemistry

, volume 2019 , issue 31-32 , pages 5475-5485

Synthesis of 1-Substituted Pyrazolines by Reaction of Donor-Acceptor Cyclopropanes with 1,5-Diazabicyclo[3.1.0]hexanes

Alexey O Chagarovskiy ^{1, 2}

V. V. Kuznetsov ²

Olga Ivanova ^{2, 3}

Alexander S. Goloveshkin ⁴

Irina Levina ⁵

Nina N. Makhova ²

Igor V Trushkov ^{1, 2}

Hide authors affiliations Show authors affiliations: 5 affiliations

Oncology and Immunology Dmitry Rogachev National Research Center of Pediatric Hematology 117997 Russian Federation |

N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences Leninsky pr. 47 119991 Moscow Russian Federation |

Department of Chemistry M. V. Lomonosov Moscow State University Leninskie Gory 1–3 119991 Moscow Russian Federation |

⁴

A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences Vavilova 28 119991 Moscow Russian Federation |

⁵

N. M. Emanuel Institute of Biochemical Physics Russian Academy of Sciences Kosygina 4 119334 Moscow Russian Federation |

Publication type: Journal Article

Publication date: 2019-06-13

Wiley

European Journal of Organic Chemistry

scimago Q2

wos Q2

SJR: 0.558

CiteScore: 4.3

Impact factor: 2.7

ISSN: 1434193X, 10990690

DOI: 10.1002/ejoc.201900579

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Organic Chemistry

Physical and Theoretical Chemistry

Abstract

Substituted pyrazolines were obtained by Ni(ClO₄)₂·6H₂O‐catalyzed reaction of 1,5‐diazabicyclo[3.1.0]hexanes with donor‐acceptor cyclopropanes. The mechanism of this reaction includes alkylation of diaziridine nitrogen with Lewis acid‐activated donor‐acceptor cyclopropane followed by hydration of the formed 1,6‐zwitterionic intermediate and oxidation of pyrazolidine with air oxygen. This pathway is realized when starting bicyclic diaziridines have bulky alkyl substituent(s) at the C(6) atom preventing (3+3)‐annulation of two three‐membered rings.

Found

3 citations

Goloveshkin Alexander

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PhD in Chemistry

145 publications, 1 923 citations

h-index: 24

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

Non-valent interactions

Quantum Chemistry

X-ray diffraction (XRD)

2 citations

Fershtat Leonid

DSc in Chemistry

146 publications, 2 959 citations, 121 reviews

h-index: 29

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

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Chagarovskiy A. O. et al. Synthesis of 1-Substituted Pyrazolines by Reaction of Donor-Acceptor Cyclopropanes with 1,5-Diazabicyclo[3.1.0]hexanes // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 31-32. pp. 5475-5485.

GOST all authors (up to 50) Copy

Chagarovskiy A. O., Kuznetsov V. V., Ivanova O., Goloveshkin A. S., Levina I., Makhova N. N., Trushkov I. V. Synthesis of 1-Substituted Pyrazolines by Reaction of Donor-Acceptor Cyclopropanes with 1,5-Diazabicyclo[3.1.0]hexanes // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 31-32. pp. 5475-5485.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/ejoc.201900579

UR - https://doi.org/10.1002/ejoc.201900579

TI - Synthesis of 1-Substituted Pyrazolines by Reaction of Donor-Acceptor Cyclopropanes with 1,5-Diazabicyclo[3.1.0]hexanes

T2 - European Journal of Organic Chemistry

AU - Chagarovskiy, Alexey O

AU - Kuznetsov, V. V.

AU - Ivanova, Olga

AU - Goloveshkin, Alexander S.

AU - Levina, Irina

AU - Makhova, Nina N.

AU - Trushkov, Igor V

PY - 2019

DA - 2019/06/13

PB - Wiley

SP - 5475-5485

IS - 31-32

VL - 2019

SN - 1434-193X

SN - 1099-0690

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2019_Chagarovskiy,

author = {Alexey O Chagarovskiy and V. V. Kuznetsov and Olga Ivanova and Alexander S. Goloveshkin and Irina Levina and Nina N. Makhova and Igor V Trushkov},

title = {Synthesis of 1-Substituted Pyrazolines by Reaction of Donor-Acceptor Cyclopropanes with 1,5-Diazabicyclo[3.1.0]hexanes},

journal = {European Journal of Organic Chemistry},

year = {2019},

volume = {2019},

publisher = {Wiley},

month = {jun},

url = {https://doi.org/10.1002/ejoc.201900579},

number = {31-32},

pages = {5475--5485},

doi = {10.1002/ejoc.201900579}

}

MLA

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MLA Copy

Chagarovskiy, Alexey O., et al. “Synthesis of 1-Substituted Pyrazolines by Reaction of Donor-Acceptor Cyclopropanes with 1,5-Diazabicyclo[3.1.0]hexanes.” European Journal of Organic Chemistry, vol. 2019, no. 31-32, Jun. 2019, pp. 5475-5485. https://doi.org/10.1002/ejoc.201900579.

Publisher

Wiley

Journal

European Journal of Organic Chemistry

scimago Q2

wos Q2

SJR

0.558

CiteScore

4.3

Impact factor

2.7

ISSN

1434193X (Print)

10990690 (Electronic)

Labs

Laboratory of Nitrogen-Containing Compounds

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