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

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

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2019, Volume: 55, Number: 11, Pages: 1716-1725 Pages count : 10 DOI: 10.1134/S1070428019110125

Tags

2-alkylamino-1,4-naphthoquinones; 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones; 13-R-benzo[f]isohromeno[4,3-b]indole-5,7,12(13H)-triones; 2,2-dihydroxy-1H-indene-1,3-(2H)-dione; domino reactions; acid catalysis

Authors

Gornostaev L.M. ¹ , Fominykh O., I ¹ , Lavrikova T., I ¹ , Khalyavina Yu G. ¹ , Gatilov Yu, V ^2,3 , Stashina G.A. ⁴

Affiliations

1	(Данные Web of science) Astafev Krasnoyarsk State Pedag Univ, Ul A Lebedevoi 89, Krasnoyarsk 660049, Russia
2	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Pr Akad Lavrentieva 9, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Ul Pirogova 2, Novosibirsk 630090, Russia
4	(Данные Web of science) Russian Acad Sci, Zelinskii Inst Organ Chem, Leninskii Pr 47, Moscow 119991, Russia

The reaction of 2-amino-1,4-naphthoquinones with ninhydrin at 50-60 degrees 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.

Gornostaev L.M. , Fominykh O.,.I. , Lavrikova T.,.I. , Khalyavina Y.G. , Gatilov Y.V. , Stashina G.A.
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. V.55. N11. P.1716-1725. DOI: 10.1134/S1070428019110125 WOS Scopus РИНЦ

Горностаев Л.М. , Фоминых О.И. , Лаврикова Т.И. , Халявина Ю.Г. , Гатилов Ю.В. , Сташина Г.А.
Особенности взаимодействия 2-амино-1,4-нафтохинонов с 2,2-дигидрокси-1H-инден-1,3(2H)-дионом
Журнал органической химии (RUSS J ORG CHEM+). 2019. Т.55. №11. С.1751-1761. DOI: 10.1134/S0514749219110132 РИНЦ

Published print:	Nov 1, 2019
Published online:	Jan 7, 2020

Web of science	WOS:000511152000012
Scopus	2-s2.0-85077542485
Elibrary	43225314
OpenAlex	W3000279266