THE PRODUCTS OF THE PHOTOLYSIS OF 2-(4-ALKYL( OR PHENYL)PIPERAZINO)-3-AMINO-1,4-NAPHTHOQUINONES, THEIR STRUCTURES AND SUBSEQUENT THERMAL TRANSFORMATIONS

THE PRODUCTS OF THE PHOTOLYSIS OF 2-(4-ALKYL( OR PHENYL)PIPERAZINO)-3-AMINO-1,4-NAPHTHOQUINONES, THEIR STRUCTURES AND SUBSEQUENT THERMAL TRANSFORMATIONS Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 1993, Volume: 42, Number: 5, Pages: 903-908 Pages count : 6 DOI: 10.1007/BF00698958

Tags

1,4-NAPHTHOQUINONE; 1,2,3,4,12,12A-HEXAHYDRONAPHTHO[2',3'/4,5]IMIDAZO[1,2-A]PYRAZINE-6,11-DIOL; 1,2,3,4-TETRAHYDRO-13-ALKYL(PHENYL)-3,1-(IMINOETHANO)BENZOL[G]QUINOXA-LINE-5,10-DIOL(-DIONE); PHOTOLYSIS; THERMOLYSIS; RECYCLIZATION; H-1 AND C-13 NMR SPECTRA

Authors

Berezhnaya V.N. ¹ , Vetchinov V.P. ¹ , Mamatyuk V.I. ¹ , Shishkina R.P. ¹

Affiliations

1	Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation

Photolysis of 2-(4-alkyl(phenyl)piperazino)-3-amino-1,4-naphthoquinones affords 2-alkyl(phenyl)-1,2,3,4,12,12a-hexahydronaphtho[2',3':4,5]imidazo[1,2-a]pyrazine-6,11-diols which recyclize at elevated temperatures to yield 1,2,3,4-tetrahydro-13-alkyl(phenyl)-3,1-(iminoethano)benzo[g]quinoxaline-5,10-diols. The latter are oxidated with atmospheric oxygen to the corresponding diones. On the basis of deuterium exchange data a mechanism for the recyclization is proposed.

Berezhnaya V.N. , Vetchinov V.P. , Mamatyuk V.I. , Shishkina R.P.
THE PRODUCTS OF THE PHOTOLYSIS OF 2-(4-ALKYL( OR PHENYL)PIPERAZINO)-3-AMINO-1,4-NAPHTHOQUINONES, THEIR STRUCTURES AND SUBSEQUENT THERMAL TRANSFORMATIONS
Russian Chemical Bulletin. 1993. V.42. N5. P.903-908. DOI: 10.1007/BF00698958 WOS Scopus РИНЦ

Published print:

May 1, 1993

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