Journal of Organic Chemistry

, volume 86 , issue 10 , pages 7218-7228

Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines.

Nikolay V Shcherbakov ¹

Dmitry Dar’in ¹

Vadim Yu. Kukushkin ^{1, 2}

Alexey Yu Dubovtsev ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation |

South Ural State University, 454080 Chelyabinsk, Russian Federation |

Publication type: Journal Article

Publication date: 2021-05-07

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.1c00558

Copy DOI

PubMed ID: 33961747

Organic Chemistry

Abstract

Gold(I)-catalyzed hetero-tetradehydro-Diels-Alder cycloaddition of enynamides and cyanamides comprises an efficient route to diversely substituted 2,6-diaminopyridines (28 examples; yields up to 99%). The reaction proceeds under very mild conditions (DCM, rt) with high functional group tolerance. The obtained 2,6-diaminopyridines represent a useful synthetic platform with an easily modulated substitution pattern for subsequent functionalizations of both the pyridine core and the N-substituents.

Found

1 citation

Kinzhalov Mikhail

🥼 🤝

DSc in Chemistry, associate professor

94 publications, 1 894 citations

h-index: 27

National Research Tomsk Polytechnic University

Saint Petersburg State University

Research interests

Coordination Chemistry

Non-covalent Interactions

Organic Chemistry

Organometallic Chemistry

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Shcherbakov N. V. et al. Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines. // Journal of Organic Chemistry. 2021. Vol. 86. No. 10. pp. 7218-7228.

GOST all authors (up to 50) Copy

Shcherbakov N. V., Dar’in D., Kukushkin V. Y., Dubovtsev A. Yu. Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines. // Journal of Organic Chemistry. 2021. Vol. 86. No. 10. pp. 7218-7228.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.1c00558

UR - https://doi.org/10.1021/acs.joc.1c00558

TI - Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines.

T2 - Journal of Organic Chemistry

AU - Shcherbakov, Nikolay V

AU - Dar’in, Dmitry

AU - Kukushkin, Vadim Yu.

AU - Dubovtsev, Alexey Yu

PY - 2021

DA - 2021/05/07

PB - American Chemical Society (ACS)

SP - 7218-7228

IS - 10

VL - 86

PMID - 33961747

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Shcherbakov,

author = {Nikolay V Shcherbakov and Dmitry Dar’in and Vadim Yu. Kukushkin and Alexey Yu Dubovtsev},

title = {Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines.},

journal = {Journal of Organic Chemistry},

year = {2021},

volume = {86},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/acs.joc.1c00558},

number = {10},

pages = {7218--7228},

doi = {10.1021/acs.joc.1c00558}

}

MLA

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MLA Copy

Shcherbakov, Nikolay V., et al. “Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines..” Journal of Organic Chemistry, vol. 86, no. 10, May. 2021, pp. 7218-7228. https://doi.org/10.1021/acs.joc.1c00558.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)

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