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Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione. / Gornostaev, L. M.; Fominykh, O. I.; Lavrikova, T. I. et al.

In: Russian Journal of Organic Chemistry, Vol. 55, No. 11, 01.11.2019, p. 1716-1725.

Research output: Contribution to journal › Article › peer-review

Harvard

Gornostaev, LM, Fominykh, OI, Lavrikova, TI, Khalyavina, YG, Gatilov, YV & Stashina, GA 2019, 'Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione', Russian Journal of Organic Chemistry, vol. 55, no. 11, pp. 1716-1725. https://doi.org/10.1134/S1070428019110125

APA

Gornostaev, L. M., Fominykh, O. I., Lavrikova, T. I., Khalyavina, Y. G., Gatilov, Y. V., & Stashina, G. A. (2019). Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione. Russian Journal of Organic Chemistry, 55(11), 1716-1725. https://doi.org/10.1134/S1070428019110125

Vancouver

Gornostaev LM, Fominykh OI, Lavrikova TI, Khalyavina YG, Gatilov YV, Stashina GA. Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione. Russian Journal of Organic Chemistry. 2019 Nov 1;55(11):1716-1725. doi: 10.1134/S1070428019110125

Author

Gornostaev, L. M. ; Fominykh, O. I. ; Lavrikova, T. I. et al. / Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione. In: Russian Journal of Organic Chemistry. 2019 ; Vol. 55, No. 11. pp. 1716-1725.

BibTeX

@article{39a9afccbeb14a2c8f1ab732ce187b2e,
title = "Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione",
abstract = "The reaction of 2-amino-1,4-naphthoquinones with ninhydrin at 50–60°C in acetic acid leads to 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones. The products were isolated as hydrates, and, when heated in DMSO with methanesulfonic acid or in acetic acid in the presence of sulfuric acid, they converted into 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones. The rate of the conversion of 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones to 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones in solutions of sulfuric acid in acetic acid is linearly related to the Hammett acidity function.",
keywords = "13-R-benzo[f]isohromeno[4,3-b]indole-5,7,12(13H)-triones, 2,2-dihydroxy-1H-indene-1,3-(2H)-dione, 2-alkylamino-1,4-naphthoquinones, 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones, acid catalysis, domino reactions, 5-HYDROXY-1,4-NAPHTHOQUINONE, DERIVATIVES",
author = "Gornostaev, {L. M.} and Fominykh, {O. I.} and Lavrikova, {T. I.} and Khalyavina, {Yu G.} and Gatilov, {Yu V.} and Stashina, {G. A.}",
year = "2019",
month = nov,
day = "1",
doi = "10.1134/S1070428019110125",
language = "English",
volume = "55",
pages = "1716--1725",
journal = "Russian Journal of Organic Chemistry",
issn = "1070-4280",
publisher = "Maik Nauka-Interperiodica Publishing",
number = "11",

}

RIS

TY - JOUR

T1 - Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione

AU - Gornostaev, L. M.

AU - Fominykh, O. I.

AU - Lavrikova, T. I.

AU - Khalyavina, Yu G.

AU - Gatilov, Yu V.

AU - Stashina, G. A.

PY - 2019/11/1

Y1 - 2019/11/1

N2 - The reaction of 2-amino-1,4-naphthoquinones with ninhydrin at 50–60°C in acetic acid leads to 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones. The products were isolated as hydrates, and, when heated in DMSO with methanesulfonic acid or in acetic acid in the presence of sulfuric acid, they converted into 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones. The rate of the conversion of 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones to 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones in solutions of sulfuric acid in acetic acid is linearly related to the Hammett acidity function.

AB - The reaction of 2-amino-1,4-naphthoquinones with ninhydrin at 50–60°C in acetic acid leads to 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones. The products were isolated as hydrates, and, when heated in DMSO with methanesulfonic acid or in acetic acid in the presence of sulfuric acid, they converted into 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones. The rate of the conversion of 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones to 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones in solutions of sulfuric acid in acetic acid is linearly related to the Hammett acidity function.

KW - 13-R-benzo[f]isohromeno[4,3-b]indole-5,7,12(13H)-triones

KW - 2,2-dihydroxy-1H-indene-1,3-(2H)-dione

KW - 2-alkylamino-1,4-naphthoquinones

KW - 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones

KW - acid catalysis

KW - domino reactions

KW - 5-HYDROXY-1,4-NAPHTHOQUINONE

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85077542485&partnerID=8YFLogxK

U2 - 10.1134/S1070428019110125

DO - 10.1134/S1070428019110125

M3 - Article

AN - SCOPUS:85077542485

VL - 55

SP - 1716

EP - 1725

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 11

ER -

ID: 23144678