TY - JOUR

T1 - Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction

AU - Ivanov, Konstantin S

AU - Samburskiy, Denis E

AU - Zargarova, Leila V

AU - Komarov, Vladislav Yu

AU - Mostovich, Evgeny A

N1 - This work was supported by the Ministry of Science and Higher Education of the Russian Federation under project No. FSUS-2021-0014. Resource Center “VTAN” (Novosibirsk State University) is acknowledged for access to experimental equipment, and Multi-Access Chemical Research Center SB RAS is acknowledged for spectral and analytical measurements.

PY - 2023/8/4

Y1 - 2023/8/4

N2 - 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.

AB - 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.

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85166432133&origin=inward&txGid=5511259439491786069bbc0f3ddd8ab1

UR - https://www.mendeley.com/catalogue/07ff1c0d-b8ea-32e2-8bca-6a7ce54f6cdf/

U2 - 10.1021/acs.joc.3c00981

DO - 10.1021/acs.joc.3c00981

M3 - Article

C2 - 37462945

VL - 88

SP - 11003

EP - 11009

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -