Journal of Organic Chemistry

, volume 88 , issue 15 , pages 11003-11009

Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction

Konstantin S. Ivanov ¹

Denis E. Samburskiy ¹

Leila V Zargarova ^{1, 2}

Vladislav Yu. Komarov ²

Vladislav Komarov ²

Evgeny A. Mostovich ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Laboratory of Low-carbon Chemical Technologies, ORËL Research Lab, Novosibirsk State University, Novosibirsk 630090, Russia |

Nikolaev Institute of Inorganic Chemistry SB RAS, Novosibirsk 630090, Russia |

Publication type: Journal Article

Publication date: 2023-07-18

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.3c00981

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PubMed ID: 37462945

Organic Chemistry

Abstract

A method for the synthesis of both symmetric and asymmetric fused spiro[4.4]-nonane-dione derivatives has been developed. It is based on a Diels–Alder reaction of spiro[4.4]nona-2,7-diene-1,6-dione as a dienophile component followed by immediate aromatization of the adduct. An active diene component can be generated using the tetrabromoxylene/NaI system, the 1,3-diphenylisobenzofuran/BF3 system, or substituted cyclones.

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Ivanov K. S. et al. Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction // Journal of Organic Chemistry. 2023. Vol. 88. No. 15. pp. 11003-11009.

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Ivanov K. S., Samburskiy D. E., Zargarova L. V., Komarov V. Y., Komarov V., Mostovich E. A. Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction // Journal of Organic Chemistry. 2023. Vol. 88. No. 15. pp. 11003-11009.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.3c00981

UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00981

TI - Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction

T2 - Journal of Organic Chemistry

AU - Ivanov, Konstantin S.

AU - Samburskiy, Denis E.

AU - Zargarova, Leila V

AU - Komarov, Vladislav Yu.

AU - Komarov, Vladislav

AU - Mostovich, Evgeny A.

PY - 2023

DA - 2023/07/18

PB - American Chemical Society (ACS)

SP - 11003-11009

IS - 15

VL - 88

PMID - 37462945

SN - 0022-3263

SN - 1520-6904

ER -

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BibTex (up to 50 authors) Copy

@article{2023_Ivanov,

author = {Konstantin S. Ivanov and Denis E. Samburskiy and Leila V Zargarova and Vladislav Yu. Komarov and Vladislav Komarov and Evgeny A. Mostovich},

title = {Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction},

journal = {Journal of Organic Chemistry},

year = {2023},

volume = {88},

publisher = {American Chemical Society (ACS)},

month = {jul},

url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c00981},

number = {15},

pages = {11003--11009},

doi = {10.1021/acs.joc.3c00981}

}

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Ivanov, Konstantin S., et al. “Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction.” Journal of Organic Chemistry, vol. 88, no. 15, Jul. 2023, pp. 11003-11009. https://pubs.acs.org/doi/10.1021/acs.joc.3c00981.