Synthesis and Spectral Properties of N-Aryl-5-hydroxy-1,4-naphthoquinone 4-Imines

Bukhtoyarova, A. D.; Ektova, L. V.; Alekseev, S. N.; Beregovaya, I. V.

doi:10.1023/b:rujo.0000010219.20915.5f

Cited by 7 publications

(6 citation statements)

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“…With regard to the synthesis of N -phenyl-1,4-naphthoquinone monoimines, Bukhtoyarova et al [19], has described their preparation by reaction of 1,5-DHN ( 1 ) with phenylamines using oxidants such as K 3 Fe(CN) 6 , HIO 3 and NaIO 4 in aqueous alcohol. According to these authors, the oxidative phenylamination mechanism involves a radical cation intermediate generated by an electron transfer process from the phenylamine to the oxidant.…”

Section: Resultsmentioning

confidence: 99%

“…The N -phenylquinone imines are considered as an important class of compounds because of their properties as dyes for optical devices [ 15 ], antioxidants [ 16 ], anticancer agents [ 17 ] and precursors of liquid crystalline materials [ 18 ]. With regard to the synthesis of N -phenyl-1,4-naphthoquinone monoimines, Bukhtoyarova et al [ 19 ], has described their preparation by reaction of 1,5-DHN ( 1 ) with phenylamines using oxidants such as K 3 Fe(CN) 6 , HIO 3 and NaIO 4 in aqueous alcohol. According to these authors, the oxidative phenylamination mechanism involves a radical cation intermediate generated by an electron transfer process from the phenylamine to the oxidant.…”

Section: Resultsmentioning

confidence: 99%

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Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

Benites¹,

Meléndez²,

Estela³

et al. 2014

Beilstein J. Org. Chem.

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SummaryA number of N-phenyl-1,4-naphthoquinone monoimines 6–10 were prepared by on-water oxidative phenylamination of 1,5-dihydroxynaphthalene (1) and 5-acetylamino-1-hydroxynaphthalene (5) with oxygen-substituted phenylamines under aerobic conditions and either solar or green LED radiation, in the presence of rose bengal as singlet oxygen sensitizer. As compared to the conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions “on water” instead of hazardous oxidant reagents currently employed in aqueous alcoholic media.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

Benites¹,

Meléndez²,

Estela³

et al. 2014

Beilstein J. Org. Chem.

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“…1). 11 The synthesized dyes (3, 5a,b-f, 6e, 8) show the characteristic long wavelength thio-substituted quinonoid π-π* broad transition at 432 ~ 471 nm.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Spectral Properties of Novel Thionaphtoquinone Dyes

Sayıl¹,

Ibis²

2010

Bulletin of the Korean Chemical Society

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2,3-Dichloro-1,4-naphtoquinone 1 compound was reacted with octadecanethiol 2 in two different mole ratio. Compound 3 was obtained from the reaction of 1 and 2 in 1:2 mole/mole ratio. Compounds 7 and 8 were obtained from reaction of 1 and 2 in 1:1 mole/mole ratio and known compound 9 was synthesized as by-product in this reaction. Novel compounds 5a-e were obtained from reaction of 1 and related thiols 4a-e. Known compounds 6c and 6e were synthesized as by-product in this reaction. The structures of the compounds were characterized by elemental analysis, UV-vis, FTIR, 1 H-NMR, 13 C-NMR and Mass spectroscopies.

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“…We found that 2,6,8-tribromo-5-hydroxy-N-phenyl-1,4-naphthoquinone 4-imine (Ia) prepared formerly from 2,4,6,8-tetrabromo-1,5-dihydroxynaphthalene [9] at boiling with n-butylamine or n-heptylamine in ethanol under basic catalysis (in the presence of K 2 CO 3 ) or with excess aniline The reaction of 2,6-dibromo-5-hydroxy-N-phenyl-1,4-naphthoquinone 4-imine (Ib) [7] with aniline in the presence of an oxidant gave rise to a mixture of 6-bromo-5-hydroxy-2-phenylamino-N-phenyl-1,4-naphthoquinone 4-imine (III) and 2,6-dibromo-4,8-di(phenylamino)-1,5-naphthoquinone (IV). EKTOVA et al…”

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confidence: 99%

“…Molecular mass and elemental composition of compounds was determined from the precision measurement of molecular ions mass on Finnigan MAT 8200 and Finnigan AEI MS-900 instruments. Initial 2,6,8-tribromo-5-hydroxy-N-phenyl-1,4-naphthoquinone 4-imine (Ia) and 2,6-dibromo-5-hydroxy-Nphenyl-1,4-naphthoquinone 4-imine (Ib) were obtained as described in [7], 2,6,8-tribromo-N-(4-butoxyphenyl)-5-hydroxy-1,4-naphthoquinone 4-imine (Ic) was prepared by procedure from [9].…”

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confidence: 99%