Tetrahedron Letters

, volume 57 , issue 1 , pages 11-14

Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

Andrey S. Mikhaylov ^{1, 2}

Alexander D Dilman ^{1, 2}

Roman G. Novikov ^{1, 2}

Yulia A Khoroshutina ^{1, 2}

Marina I. Struchkova ^{1, 2}

Dmitry E. Arkhipov ^{3, 4}

Yulia V. Nelyubina ⁵

Andrey A Tabolin ^{1, 2}

Sema L. Ioffe ^{1, 2}

Hide authors affiliations Show authors affiliations: 5 affiliations

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences |

Leninsky prosp. 47 119991 Moscow Russian Federation |

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

⁴

N. I. Pirogov Russian National Research Medical University, Ostrovityanova str. 1, 117997 Moscow, Russian Federation |

⁵

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

Publication type: Journal Article

Publication date: 2016-01-01

Elsevier

Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.334

CiteScore: 3.2

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/j.tetlet.2015.10.091

Copy DOI

Organic Chemistry

Drug Discovery

Biochemistry

Abstract

The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C–C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.

Found

2 citations

Sukhorukov Alexey

DSc in Chemistry

123 publications, 1 616 citations, 97 reviews

h-index: 22

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

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

Research interests

Medicinal Chemistry

Organic Chemistry

2 citations

Dilman Alexander

DSc in Chemistry, associate member of the Russian Academy of Sciences

208 publications, 5 124 citations, 152 reviews

h-index: 39

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

Research interests

Organic Chemistry

1 citation

Andreev Ivan

PhD in Chemistry

41 publications, 495 citations, 10 reviews

h-index: 12

Peoples' Friendship University of Russia

Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology

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

1 citation

Nelyubina Yulia

🤝

DSc in Chemistry

506 publications, 7 574 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

1 citation

Perekalin Dmitry

🥼

DSc in Chemistry

121 publications, 1 961 citations, 35 reviews

h-index: 25

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

Research interests

Asymmetric metal complex catalysis

Catalysis

Organometallic Chemistry

Photochemistry

1 citation

Antonova Yulia

🤝

8 publications, 48 citations

h-index: 3

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

1 citation

Chusov Denis

DSc in Chemistry, professor

97 publications, 2 368 citations, 35 reviews

h-index: 24

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

Research interests

Asymmetric metal complex catalysis

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GOST |

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GOST Copy

Mikhaylov A. S. et al. Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes // Tetrahedron Letters. 2016. Vol. 57. No. 1. pp. 11-14.

GOST all authors (up to 50) Copy

Mikhaylov A. S., Dilman A. D., Novikov R. G., Khoroshutina Y. A., Struchkova M. I., Arkhipov D. E., Nelyubina Y. V., Tabolin A. A., Ioffe S. L. Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes // Tetrahedron Letters. 2016. Vol. 57. No. 1. pp. 11-14.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.tetlet.2015.10.091

UR - https://doi.org/10.1016/j.tetlet.2015.10.091

TI - Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

T2 - Tetrahedron Letters

AU - Mikhaylov, Andrey S.

AU - Dilman, Alexander D

AU - Novikov, Roman G.

AU - Khoroshutina, Yulia A

AU - Struchkova, Marina I.

AU - Arkhipov, Dmitry E.

AU - Nelyubina, Yulia V.

AU - Tabolin, Andrey A

AU - Ioffe, Sema L.

PY - 2016

DA - 2016/01/01

PB - Elsevier

SP - 11-14

IS - 1

VL - 57

SN - 0040-4039

SN - 1873-3581

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2016_Mikhaylov,

author = {Andrey S. Mikhaylov and Alexander D Dilman and Roman G. Novikov and Yulia A Khoroshutina and Marina I. Struchkova and Dmitry E. Arkhipov and Yulia V. Nelyubina and Andrey A Tabolin and Sema L. Ioffe},

title = {Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes},

journal = {Tetrahedron Letters},

year = {2016},

volume = {57},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/j.tetlet.2015.10.091},

number = {1},

pages = {11--14},

doi = {10.1016/j.tetlet.2015.10.091}

}

MLA

Cite this

MLA Copy

Mikhaylov, Andrey S., et al. “Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes.” Tetrahedron Letters, vol. 57, no. 1, Jan. 2016, pp. 11-14. https://doi.org/10.1016/j.tetlet.2015.10.091.

Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.334

CiteScore

3.2

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)

Labs

Molecular Structure Research Center

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