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Doctoral Thesis
DOI
https://doi.org/10.11606/T.46.1986.tde-19062015-170901
Document
Author
Full name
Solange de Lima Netto
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1986
Supervisor
 
Title in Portuguese
Síntese de xiloquinonas 2, 3-dissubstituídas
Keywords in Portuguese
Química orgânica
Síntese orgânica
Abstract in Portuguese
É apresentada a revisão bibliográfica de reações entre dicloronaftoquinona e nucleófilos de enxofre, nitrogênio e carbono. São descritas as reações de 2,3-dihalogeno-xiloquinonas com os mesmos nucleófilos, sendo isolados e caracterizadas, no total, 18 xiloquinonas substituídas novas. Enquanto, que as reações com nucleófilos de enxofre conduziram aos derivados ditio-substituídos, não sendo possível obter derivados monossubstituídos, no caso de nucleófilos de nitrogênio e carbono isolaram-se somente derivados monossubstituídos. Dentre as xiloquinonas substituídas, fazem parte vários derivados mistos de nitrogênio-enxofre, carbono -enxofre e carbono-nitrogênio. Foram também sintetizados e caracterizados dois novos mono-sulfinil derivados obtidos pela oxidação de dimetiltio-xiloquinona e dimetiltio-naftoquinona. Foi descrita uma nova reação entre mono sulfinil-metiltio-xiloquinona e cloreto de tionila, conduzindo à cloro-metiltio-xiloquinona. São discutidas as diferenças de reatividade e sugeridos os mecanismos para as reações descritas. São também apresentados os resultados de testes bacteriológicos preliminares.
 
Title in English
Synthesis of xiloquinonas of 2,3 - disubstituted
Keywords in English
Organic chemistry
Organic synthesis
Abstract in English
The literature review of the reactions of dichloronafhtoquinone with nucleophiles of sulphur, nitrogen and carbon is presented. The experimental results of the reactions of 2,3-dihalogeno- xyloquinones with the same nucleophiles are reported, being isolated and identified 18 new 2,3-substituted xyloquinones. These are: di-sulphur, mono-nitrogen and mono-carbon, as well as nitrogen-sulphur, carbon-sulphur and carbon-nitrogen mixed substituted derivatives. No mono-sulphur or di-nitrogen or di-carbon-substituted xyloquinones could be isolated. Two new mono-sulphinyl derivatives, obtained by oxidation of dimethylthioxyloquinone and dimethylthionaphtoquinone, were isolated and identified. A new reaction between 2-sulphinyl-3-methylthioxyloquinone and thionyl chloride, leading to the 2-chloro-3-methylthioxyloquinone is described. The reactivity differences are discussed and the reaction mechanisms proposed. The preliminary test, reported for some new substituted xyloquinones, indicate that aziridinyl- and chloro-derivatives are biologically active.
 
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Publishing Date
2015-06-23
 
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