RESUMO
Isopropyl-alkylamines 2 react with 2,3-dichloro-1,4-naphthoquinone (1) to give red 2-chloro-3-isopropyl-alkylamino-1,4-naphthoquinones 3 and with 2,3-dichloro-1,4-naphthoquinone/acetaldehyde to give blue 2-chloro-3-isopropylalkylamino-vinyl-1,4-naphthoquinones 7. It is evident that the formation of 7 is preferred sterically to the formation of 3. The reaction between 2, 1 and acetaldehyde give also red aminoquinones 3 and blue green 2-chloro-3-(4-isopropylalkylamino-buta-1,3-dienyl)-1,4-naphthoquinone like 11.
Assuntos
Naftoquinonas/química , Acetaldeído , Corantes , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Conformação Molecular , Propilaminas/química , Espectrofotometria InfravermelhoRESUMO
Dialkylamine drugs desipramine, propanolol, pindolol, alprenolol and metoprolol 4a-e react with 2,3-dichloro-1,4-naphthoquinone (2) and acetaldehyde to give red coloured 2-dialkylamino-3-chloro-1,4-naphthoquinones 5a, b, d, e, blue coloured 2-dialkylamino-vinyl-3-chloro-1,4-naphtho-quinones 1a-e and bluish green coloured 2-dialkylamino-butadienyl-3-chloro-1,4-naphthoquinones 6b-e. The colour products are isolated by column chromatography.
Assuntos
Acetaldeído/química , Naftoquinonas/química , Preparações Farmacêuticas/química , Cromatografia , Colorimetria , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Sodium 1,2-naphthoquinone-4-sulphonate (1) reacts with trialkylamines 6a, b by N-desalkylation to give red colored 4-di-alkyamino-1,2-naphthoquinones 3a, b. N,N-Diethylaniline (6f), a phenylogous amine, reacts with 1 to form the blue colored 4-(diethylamino-phenyl)-1,2-naphthoquinone (8). 2,3-Dihalogeno-1,4-naphthoquinones 15A/B produce with triethylamine (6a) the red N-desalkylation products 17A/Ba and the blue colored dehydrogenation products 18A/B. The reactions from trialkylamines 6b-g indicate that only ethyl functions may be dehydrogenated. 2,3-Dihalogeno-1,4-naphthoquinones 15A/B form with N,N-Diethylaniline (6f) blue violet colored CT-complexes and with diethylcyclohexylamine (6g) only blue colored 2-aminovinyl-3-halogeno-1,4-naphthoquinones 20A/B.
Assuntos
Alcinos/química , Aminas/química , Corantes/química , Naftoquinonas/química , Cor , Remoção de Radical Alquila , Indicadores e ReagentesRESUMO
1,2-Naphthoquinone (8) reacts with arylhydrazines 2 in acetic solution to give 1,2-naphthoquinone-2-arylhydrazones 13 and 2-arylazo-1-naphtholes, respectively. 4-Arylhydrazino-1,2-naphthoquinones 11 are not obtained. On the other hand 8 reacts with the same arylhydrazones 2 in neutral methanolic solution to give 11 and 13. The formation of 13 is remarkable, because 1,4-naphthoquinone (1) does not react with arylhydrazones 2 in neutral methanolic solution to give 6 and because arylhydrazones usually are condensed in acidic solution.
Assuntos
Hidrazinas/química , Naftoquinonas/química , Espectroscopia de Ressonância Magnética , Espectrofotometria InfravermelhoRESUMO
2-Arylamino-3-dichloroacetylamino-1,4-naphthoquinones 4 show in ethanolic hydrochloric acid the same reactivity as the corresponding 3-monochloroacetylamino-1,4-naphthoquinones 3. After cyclisation from 4 to 6, 6 dehydrates to give 2-dichloromethyl-4,9-dihydro-1-phenyl-1H-napth [2,3-d]imidazole-4,9-diones 8. Elimination of dichloromethane from 6 to 9 is not observed. The reaction of 4c in alkaline DMSO solution indicates, that ring closure to 3-hydroxy-benzo[g]quinoxalinetriones 2 is possible. The microbiological activity from 7 and 8 has been proved.
