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


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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

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