Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione
- Authors: Gornostaev L.M.1, Fominykh O.I.1, Lavrikova T.I.1, Khalyavina Y.G.1, Gatilov Y.V.2,3, Stashina G.A.4
-
Affiliations:
- Astaf’ev Krasnoyarsk State Pedagogical University
- Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch
- Novosibirsk State University
- Zelinskii Institute of Organic Chemistry
- Issue: Vol 55, No 11 (2019)
- Pages: 1716-1725
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/221371
- DOI: https://doi.org/10.1134/S1070428019110125
- ID: 221371
Cite item
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.
About the authors
L. M. Gornostaev
Astaf’ev Krasnoyarsk State Pedagogical University
Author for correspondence.
Email: gornostaev@kspu.ru
Russian Federation, ul. A. Lebedevoi 89, Krasnoyarsk, 660049
O. I. Fominykh
Astaf’ev Krasnoyarsk State Pedagogical University
Email: galina_stashina@chemical-block.com
Russian Federation, ul. A. Lebedevoi 89, Krasnoyarsk, 660049
T. I. Lavrikova
Astaf’ev Krasnoyarsk State Pedagogical University
Email: galina_stashina@chemical-block.com
Russian Federation, ul. A. Lebedevoi 89, Krasnoyarsk, 660049
Yu. G. Khalyavina
Astaf’ev Krasnoyarsk State Pedagogical University
Email: galina_stashina@chemical-block.com
Russian Federation, ul. A. Lebedevoi 89, Krasnoyarsk, 660049
Yu. V. Gatilov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch; Novosibirsk State University
Email: galina_stashina@chemical-block.com
Russian Federation, pr. Akademika Lavrentieva 9, Novosibirsk, 630090; ul. Pirogova 2, Novosibirsk, 630090
G. A. Stashina
Zelinskii Institute of Organic Chemistry
Author for correspondence.
Email: galina_stashina@chemical-block.com
Russian Federation, Leninskii pr. 47, Moscow, 119991
Supplementary files
