Hydroxylation of 4-arylimino-5-hydroxy-1,4-dihydronaphthalen-1-ones

Heating of 4-arylimino-5-hydroxy-1,4-dihydronaphthalen-1-ones with sodium hydroxide in the presence of K₃Fe(CN)₆ gives the corresponding 2,5-dihydroxy derivatives, while in the reaction with FeCl₃ 6H₂O 4-arylimino-3,5-dihydroxy-1,4-dihydronaphthalen-1-ones are formed.Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1334–1336.Original Russian Text Copyright © 2004 by Bukhtoyarova, Ektova.     

Oxidative arylamination of 1,7-dihydroxynaphthalene

1,7-Dihydroxynaphthalene reacts with aniline orp-toluidine in the presence of oxidants to give the correspondingN-aryl-7-hydroxy-1,4-naphthoquinone 4-imines, 2-arylamino- and 2,8-diarylamino-N-aryl-7-hydroxy-1,4-naphthoquinone 4-imines, and benzo[a]oxophenoxazinimine derivatives. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 347–350, February, 1999.     

Dependence of Carbon Chemical Shifts in the 13C NMR Spectra of 5-Hydroxy-1,4-naphthoquinon-4-imines on Position of Tautomeric Equilibrium

In the ¹³C NMR spectra of 5-hydroxy-1,4-naphthoquinon-4-imines the para-quinonimine form is characterized by the presence of signals from C⁵ in the region 160-162 ppm and from C¹⁰ at 115 ppm whereas typical signals of the ana-quinoid form are those of C⁵ in the region 169-170 ppm and C10 at 110-11 ppm.     

Amination of 5-hydroxy-1,4-naphthoquinone in the presence of copper acetate

The reaction of 5-hydroxy-1,4-naphthoquinone with butylamine in the presence of copper(II) acetate monohydrate on heating resulted in the formation of a mixture of regioisomeric 2,6- and 2,8-bis(butylamino)-5-hydroxy-1,4-naphthoquinones.     

Synthesis of 2,4,6,8-Tetrasubstituted 1,5-Naphthoquinones

Derivatives of N-aryl-5-hydroxy-1,4-naphthoquinone 4-imines react with primary amines to afford 2,4,6,8-tetrasubstituted 1,5-naphthoquinones.     

Synthesis and properties of naphthoquinonylamino-substituted benzocrown ethers

Naphthoquinonylaminobenzocrown ethers were synthesized by reactions of 4-aminobenzocrown ethers with 1,4-naphthoquinones. A hypsochromic shift of the long-wave absorption band was found to appear in the electron spectra when the compounds synthesized reacted with alkaline or alkaline-earth metal salts.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 452–454, March, 1994.     

Synthesis and structure of N-(4-dialkylaminophenyl)hexafluoro-1,4-naphthoquinone 4-imines

The reaction of heptafluoro-1-naphthol with N,N-dialkyl-p-nitrosoanilines or N,N-dialkyl-p-phenylenediamines in the presence of HIO₃ gave the corresponding polyfluorinated N-aryl-1,4-naphthoquinone 4-imine derivatives which exist in solution as equilibrium mixtures of Z and E isomers. 2,3,5,6,7,8-Hexafluoro-N-(4-dimethylaminophenyl)-1,4-naphthoquinone 4-imine in crystal has exclusively the Z-isomer structure.     

Reaction of hexafluoro-N-(4-N,N-dialkylaminophenyl)-1,4-naphthoquinon-4-imines with primary amines

Amination of 2,3,5,6,7,8-hexafluoro-N-(4-N,N-dialkylaminophenyl)-1,4-naphthoquinon-4-imines with primary amines led to the formation of 3-amino derivatives, which further underwent cyclization into 7-alkyl(aryl)-1,2,3,4,6-pentafluoro-5H-benzo[a]phenazin-5-ones. The spectral properties of compounds obtained were examined.