Synthesis of 5,7-dihydroxynaphthoquinone derivatives and their reactions with nucleophiles: Nitration of 2,3-dimethylnaphthalene and subsequent transformations

1976 ◽  
Vol 29 (10) ◽  
pp. 2247 ◽  
Author(s):  
HJ Banks ◽  
DW Cameron ◽  
MJ Crossley ◽  
EL Samuel
Keyword(s):  
Unusual Reaction ◽  
Nitro Derivatives ◽  
Reactions With Nucleophiles ◽  
Derivatives Of ◽  
Related Compounds ◽  
Benzenoid Ring

5,7-Dihydroxy-2,3-dimethyl-l,4-naphthoquinone (5) and related compounds have been synthesized. The quinone affords an accessible substrate for studying an unusual reaction with nucleophiles, which involves attack at the 8-position, i.e. at the benzenoid ring. An unsuccessful approach to (5) has led to tri- and tetra-nitro derivatives of 2,3-dimethylnaphthalene. Reduction of the former and subsequent conversions have given aminonaphthoquinone and perimidinone derivatives.

QSAR Analysis of Selected Antimicrobial Structures Belonging to Nitro-derivatives of Heterocyclic Compounds

2020 ◽  
Vol 17 (2) ◽  
pp. 214-225 ◽  
Author(s):  
Piotr Kawczak ◽  
Leszek Bober ◽  
Tomasz Bączek
Keyword(s):  
Antimicrobial Activity ◽  
Heterocyclic Compounds ◽  
Molecular Descriptors ◽  
Microbiological Activity ◽  
Activity Data ◽  
Qsar Analysis ◽  
Qsar Models ◽  
Nitro Derivatives ◽  
Semi Empirical ◽  
Derivatives Of

Background: Nitro-derivatives of heterocyclic compounds were used as active agents against pathogenic microorganisms. A set of 4- and 5-nitroimidazole derivatives exhibiting antimicrobial activity was analyzed with the use of Quantitative Structure-Activity Relationships (QSAR) method. The study included compounds used both in documented treatment and those described as experimental. Objective: The purpose of this study was to demonstrate the common and differentiating characteristics of the above-mentioned chemical compounds alike physicochemically as well as pharmacologically based on the quantum chemical calculations and microbiological activity data. Methods: During the study PCA and MLR analysis were performed, as the types of proposed chemometric approach. The semi-empirical and ab initio level of in silico molecular modeling was performed for calculations of molecular descriptors. Results: QSAR models were proposed based on chosen descriptors. The relationship between the nitro-derivatives structure and microbiological activity data was able to class and describe the antimicrobial activity with the use of statistically significant molecular descriptors. Conclusion: The applied chemometric approaches revealed the influential features of the tested structures responsible for the antimicrobial activity of studied nitro-derivatives.

Electrochemical reduction of para-substituted 2-acyl-5-phenylfuranes in dimethylformamide

1981 ◽  
Vol 46 (2) ◽  
pp. 498-502 ◽  
Author(s):  
Jozef Černák ◽  
František Tomanovič ◽  
Andrej Staško ◽  
Anna Fedosyevna Oleinikova ◽  
Jaroslav Kováč
Keyword(s):  
Electrochemical Reduction ◽  
Unpaired Electron ◽  
Anion Radical ◽  
Electron Wave ◽  
Epr Method ◽  
Electron Center ◽  
Nitrogen Nucleus ◽  
Nitro Derivatives ◽  
Stable Anion ◽  
Derivatives Of

para Substituted chloro, bromo, and nitro derivatives of 2-acyl-5-phenylfurane are reduced polarographically in a one-electron wave to the corresponding anion radicals, which were studied by the EPR method. The reduction of nitro derivatives, studied by the Kalousek switch, is reversible and leads to a stable anion radical with an unpaired electron center on the nitrogen nucleus; the reduction of the halogen derivatives is only partly reversible and leads to unstable ketyl radicals. The bromo derivatives give polarographic maxima typical for concurrent reactions.

scholarly journals Nitro Derivatives of 4, 5-Dimethyl-carbethoxyaminobenzene

1949 ◽  
Vol 69 (11) ◽  
pp. 493-496
Author(s):  
Taizo Matskawa ◽  
Kenzo Sirakawa
Keyword(s):  
Nitro Derivatives ◽  
Derivatives Of

A synthesis of alkylated 3-aminoisoquinolines and related compounds

1982 ◽  
Vol 35 (7) ◽  
pp. 1391 ◽  
Author(s):  
AJ Liepa
Keyword(s):  
Phosphoryl Chloride ◽  
Tertiary Amides ◽  
Derivatives Of ◽  
Related Compounds ◽  
Selection Of

N,N-Dialkyl derivatives of 3-aminoisoquinoline have been prepared by reaction of nitriles with various arylacetic acid tertiary amides in the presence of phosphoryl chloride. The synthesis has been extended to include a benzoisoquinoline and annulated isoquinolines by the selection of appropriate amide and nitrile precursors.

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