SYNTHESIS OF N-HYDROXYINDOLES

2017 ◽  
Vol 60 (4) ◽  
pp. 4 ◽  
Author(s):  
Zhanna V. Chirkova
Keyword(s):  
Noble Metals ◽  
Dicarboxylic Acids ◽  
Building Blocks ◽  
Monoamine Oxidase A ◽  
Biologically Active ◽  
Synthetic Methods ◽  
Titanium Chloride ◽  
Functional Derivatives ◽  
Derivatives Of ◽  
Treat Breast Cancer

The basic synthetic methods for obtaining N-hydroxyindoles were studied. The first method is intramolecular reductive cyclization of ortho-substituted nitroaromatic compounds by various reducing agents. Nitrophenyl acetaldehydes (synthesis by Acheson), N,N-disubstituted amino-2-nitrostyrenes (synthesis by Somei), ortho-nitroketoetheres of different structure or 1-(o-nitroarene)-1-cyanoalkylnitroketones, ortho-nitrophenylacetonitriles were used as substrates for the synthesis of N-hydroxyindoles. Titanium chloride (III), zinc in THF solution of ammonium chloride or in acetic acid, stannous chloride in ethanolic HCl, and hydrogen with application of catalytic agent on basis of noble metals (platinum, palladium) were used as reduction agents. The second method is a [3+2]-cycloaddition with nitrozoaromatic compounds to alkynes or deoxygenation ortho-nitro substituted aromatic compounds with subsequent intramolecular cyclization. The third method is catalytic oxidation of 2,3-dihydroindoles or different indoles by concentrated hydrogen peroxide with application of of tungstate sodium as catalyst. We attended special attention to synthesis of functional derivatives of N-hydroxyindole-5,6-dicarboxylic acids because these compounds were synthesized from commercially available basic materials using well known synthetic methods and without using expensive catalysts. Indoles of various designs were synthesized. They may be building blocks for the synthesis of biologically active substances, phthalocyanines of different structures having mesomorphic and catalytic properties. Compounds of this class of heterocycles were found among many natural products and they can be used as therapeutic agents, for example, as inhibitors of human lactate dehydrogenase of isoforms 5, selective inhibitors of monoamine oxidase A and B, and N-methoxyindole can be used to treat breast cancer. For citation:Chirkova Zh.V. Synthesis of N-hydroxyindoles. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 4. P. 4-20.

scholarly journals Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids

Biomolecules ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 566 ◽  
Author(s):  
Akula ◽  
Kwon
Keyword(s):  
Large Scale ◽  
Dicarboxylic Acids ◽  
Cost Effective ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Aqueous Alcohol ◽  
Chemical Transformations ◽  
Hydroxycarboxylic Acids ◽  
Escherichia Coli Cells ◽  
Catalyzed Oxidation

In addition to our previous efforts toward bioenzymatic and chemical transformations of ricinoleic acid and oleic acid to their corresponding ,-dicarboxylic acids via their ester intermediates driven in Escherichia coli cells, several efficient oxidation conditions were investigated and optimized for the conversion of -hydroxycarboxylic acids to ,-dicarboxylic acids. Pd/C-catalyzed oxidation using NaBH4 in a basic aqueous alcohol and Ni(II) salt-catalyzed oxidation using aqueous sodium hypochlorite were considered to be excellent as a hybrid reaction for three successive chemical reactions (hydrogenation, hydrolysis, and oxidation) and an eco-friendly, cost-effective, and practical approach, respectively. Omega-hydroxycarboxylic acids and -aminocarboxylic acid were also easily prepared as useful building blocks for plastics or bioactive compounds from the bioenzymatically driven ester intermediate. The scope of the developed synthetic methods can be utilized for large-scale synthesis and various derivatizations.

Functional derivatives of (bi)phenyl-substituted carbazoles as building blocks for electro-active polymers

2010 ◽  
Vol 70 (7) ◽  
pp. 477-481 ◽  
Author(s):  
S. Lengvinaite ◽  
J.V. Grazulevicius ◽  
S. Grigalevicius ◽  
B. Zhang ◽  
Z. Xie
Keyword(s):  
Building Blocks ◽  
Functional Derivatives ◽  
Derivatives Of

scholarly journals Synthesis, Sorption and Metallochromy Properties of Organosilicon Derivatives of 1-Acetylguanidine

2021 ◽  
Vol 13 (1) ◽  
pp. 78-87
Author(s):  
E.N. Oborina ◽  
◽  
A.M. Nalibayeva ◽  
V.G. Fedoseeva ◽  
I.A. Ushakov ◽  
...  
Keyword(s):  
Noble Metals ◽  
Large Scale ◽  
Condensation Reaction ◽  
Building Blocks ◽  
Test Methods ◽  
Metal Extraction ◽  
Composition And Structure ◽  
Complex Test ◽  
Derivatives Of ◽  
Polymeric Structures

Increased interest in carbofunctional organosilicon monomers (silanes) and polymers (silsesquioxanes) is associated with the fact that these compounds are promising reagents and building blocks, materials for micro-electronics, agriculture and medicine, complexones, catalysts, and efficient sorbents. Thus, functional polysilsesquioxanes surpass mineral and organic sorbents in sorption properties. Moreover, they have the highest chemical and thermal stability. Along with sorption activity carbofunctional organosilicon compounds of both monomeric and polymeric structures can possess metallochromic properties. All this paves the way for the large-scale development of analytical systems for the creation of new complex test methods for the determination, concentration and separation of metals from solutions. In the present study the functional monomer N-[3-(triethoxysilyl)propyl]acetylguanidine 1 was synthesized by the condensation reaction of 1-acetylguanidine and 3-triethoxysilyl-propylamine. Poly-N-[3-silsesquioxanyl) propyl]acetylguanidine 2 was obtained by hydrolytic polycondensation of compound 1. The composition and structure of compounds 1 and 2 were confirmed by IR and 1H NMR spectroscopy, as well as by elemental analysis. Polymer 2 was studied as a sorbent for ions of heavy metals, such as Hg (II), and noble metals Ag (I), Au (III), Rh (II), Pd (II), Pt (IV) from solutions of their salts in hydrochloric or nitric acid. For polymer 2, the values of static sorption capacities have been calculated. The latter depend on the nature of the metal and have values from 78 mg/g (for platinum) to 366 mg/g for rhodium. The graphs of the degree of metal extraction depending on the sorption time and acid concentration have been plotted. A sorption mechanism is proposed, which is realized due to the chelate interaction of the metal cation (M+) with the amide groups of compounds 1 and 2. The interaction of monomer 1, in the form of indicator paper, and polymer 2, in the powder form, with salts of the studied metals is accompanied by intense specific coloration (metallochromy). Color tables of the samples after their contact with the Ag (I), Au (III), Pd (II), Pt (IV), Rh (III), Hg (II) salts are given.

Synthesis of Functional Derivatives of 3-Acyl-1-hydroxyindole-5,6-dicarboxylic Acids

2019 ◽  
Vol 89 (3) ◽  
pp. 626-630
Author(s):  
Zh. V. Chirkova ◽  
M. V. Kabanova ◽  
S. I. Filimonov
Keyword(s):  
Dicarboxylic Acids ◽  
Functional Derivatives ◽  
Derivatives Of

scholarly journals Approaches to the Synthesis of Dicarboxylic Derivatives of Bis(pyrazol-1-yl)alkanes

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 413
Author(s):  
Nikita P. Burlutskiy ◽  
Andrei S. Potapov
Keyword(s):  
Potassium Hydroxide ◽  
Oxalyl Chloride ◽  
Dicarboxylic Acids ◽  
Building Blocks ◽  
Acid Chlorides ◽  
Alternative Approach ◽  
Methylene Groups ◽  
Metal Organic ◽  
Superbasic Medium ◽  
Derivatives Of

Carboxylation of bis(pyrazol-1-yl)alkanes by oxalyl chloride was studied. It was found that 4,4′-dicarboxylic derivatives of substrates with electron-donating methyl groups and short linkers (from one to three methylene groups) can be prepared using this method. Longer linkers lead to significantly lower product yields, which is probably due to instability of the intermediate acid chlorides that are initially formed in the reaction with oxalyl chloride. Thus, bis(pyrazol-1-yl)methane gave only monocarboxylic derivative even with a large excess of oxalyl chloride and prolonged reaction duration. An alternative approach involves the reaction of ethyl 4-pyrazolecarboxylates with dibromoalkanes in a superbasic medium (potassium hydroxide–dimethyl sulfoxide) and is suitable for the preparation of bis(4-carboxypyrazol-1-yl)alkanes with both short and long linkers independent of substitution in positions 3 and 5 of pyrazole rings. The obtained dicarboxylic acids are interesting as potential building blocks for metal-organic frameworks.

Synthesis of Functional Derivatives of Benzofuran-5,6-dicarboxylic Acids

2019 ◽  
Vol 89 (6) ◽  
pp. 1307-1309
Author(s):  
Zh. V. Chirkova ◽  
S. I. Filimonov ◽  
I. G. Abramov
Keyword(s):  
Dicarboxylic Acids ◽  
Functional Derivatives ◽  
Derivatives Of

Functional Derivatives of Sterically Hindered Amines. Polyalkylpiperidine Diesters

1995 ◽  
Vol 60 (9) ◽  
pp. 1529-1535 ◽  
Author(s):  
František Vašš ◽  
Jozef Lustoň
Keyword(s):  
Dicarboxylic Acid ◽  
Nucleophilic Addition ◽  
Dicarboxylic Acids ◽  
Amino Derivative ◽  
Replacement Reaction ◽  
Structural Units ◽  
Functional Derivatives ◽  
Acid Catalyzed ◽  
Hindered Amines ◽  
Derivatives Of

Several diesters of dicarboxylic acids with pendant polyalkylpiperidine structural units were prepared from α-bromo and α,α'-dibromo substituted aliphatic dicarboxylic acid diesters by a nucleophilic replacement reaction with 2,2,6,6-tetramethyl-4-hydroxypiperidine, 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, and 2,2,6,6-tetramethyl-4-aminopiperidine, by a nucleophilic addition of amino derivative to the α,β-unsaturated dicarboxylic acid diester and by an acid catalyzed condensation of 2,2,6,6-tetramethyl-4-oxopiperidine with diethyl bis(hydroxymethyl)malonate.

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