On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid

On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid Full article

Journal

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

Output data

Year: 2019, Volume: 55, Number: 5, Pages: 608-614 Pages count : 7 DOI: 10.1134/S1070428019050051

Tags

2-benzylamino-1; 4-naphthoquinone; hydroxyimidazole; naphtho-1; 2-oxazole; oximes; 2; 3-diazido-1; 4-naphthoquinone; nitrosylsulfuric acid

Authors

Gornostaev L.M. ¹ , Nuretdinova E.V. ¹ , Lavrikova T.I. ¹ , Khalyavina Yu.G. ¹ , Fominykh O.I. ¹ , Gatilov Yu.V. ^2,3

Affiliations

1	(Данные Web of science) Astafev Krasnoyarsk State Pedag Univ, Ul A Lebedevoy 89, Krasnoyarsk 660049, Russia
2	(Данные Web of science) RAS, SB, Vorozhtsov Novosibirsk Inst Organ Chem, Pr Akad Lavrentieva 9, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Ul Pirogova 2, Novosibirsk 630090, Russia

The reaction of 2-benzylamino-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid results in preferential formation of 2,1- and 2,3-heterocyclization products: (E)-4-(hydroxyimino)-2-phenylnaphtho [2,1-d]oxazol-5(4H)-one and 2-phenyl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-dione. In addition, 2-phenylnaphtho[2,1-d]oxazol-4,5-dione and N-(3-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide are also formed. The reaction of 2-benzylamino-3-chloro-1,4-naphthoquinone with nitrosylsulfuric acid in acetic acid gives 3-diazonapthalene-1,2,4(3H)-trione and benzaldehyde.

Gornostaev L.M. , Nuretdinova E.V. , Lavrikova T.I. , Khalyavina Y.G. , Fominykh O.I. , Gatilov Y.V.
On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid
Russian Journal of Organic Chemistry. 2019. V.55. N5. P.608-614. DOI: 10.1134/S1070428019050051 WOS Scopus РИНЦ

Горностаев Л.М. , Нуретдинова Э.В. , Лаврикова Т.И. , Халявина Ю.Г. , Фоминых О.И. , Гатилов Ю.В.
О реакции 2-бензиламино-1,4-нафтохинонов с нитрозилсерной кислотой
Журнал органической химии (RUSS J ORG CHEM+). 2019. Т.55. №5. С.700-707. DOI: 10.1134/S0514749219050069 РИНЦ

Published print:	May 1, 2019
Published online:	Jul 13, 2019

Web of science	WOS:000475589400005
Scopus	2-s2.0-85068819080
Elibrary	41616973
OpenAlex	W2959587032