Electrochemical approach to obtaining flavonoid derivatives

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Flavonoids are an important class of natural products. Because of their anti-oxidative, anti-inflammatory and anti-carcinogenic properties, flavonoids underlie a number of biologically active substances. In this monograph, the possibility of obtaining new derivatives of flavonoids by an electrochemical method is considered. Particular attention is paid to electrochemical transformations of flavonoids under the conditions of electrode polarization.
The book may be of interest to specialists working in the field of organic chemistry and electrochemistry, teachers and students of chemical faculties.

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CONTENT
INTRODUCTION

5
1. GENERAL INFORMATION ON THE FLAVONOIDS
8
1.1 . Classification and structure of flavonoids
8
1.2. A brief overview of the biological activity of flavonoids
10
1.3. Synthesis of flavonoids
11
1.4. Identification of flavonoids
14
2. BASIC PRINCIPLES OF ORGANIC ELECTROSYNTHESIS
16
2.1. General issues
16
2.2. Methods for studying the electrochemical behaviour of organic compounds
17
2.2.1. Electrochemical measurements
18
2.2.2. Bulk electrolysis, with isolation and identification of electrolysis products
19
2.3. Features of electrolysis of organic compounds
20
3. ELECTROLYSIS IN AQUEOUS SOLUTIONS
25
3.1. Scheme of flavonoids transformation under the conditions of anodic polarization
25
3.2. Electrochemical oxidation of eupafolin
30
4. ELECTROLYSIS IN ACETONITRILE
38
4.1. General issues on the application of acetonitrile in organic electrochemistry
38
4.2. Cyclic voltammograms of flavonoids in acetonitrile
38
4.3. Bulk electrolysis of flavonoids in acetonitrile
42
4.3.1. Electrochemical coupling of flavonols
42
4.3.2. Synthesis of flavopiridol analogues by electrolysis of chrysine
47
4.4. Electrochemical nitration of the flavonoids
50
4.4.1. Opportunities for obtaining flavonoids nitro derivatives
50
4.4.2. Bulk electrolysis of galangin in the presence of N2O4 in a two-compartment cell
51
4
4.4.3. Bulk electrolysis of isorhamnetin in the presence of N2O4 in a three-compartment cell
52
4.4.4. Transformation of flavonoids under the conditions of electrochemical nitration
52
5. ELECTROLYSIS IN THE «ACETONITRILE-WATER» SYSTEM
55
5.1. Cyclic voltammetry
55
5.2. Rotating disc electrode
62
5.3. Bulk electrolysis
64
5.4. Electrochemical synthesis of flavopiridol analogues
65
6. ELECTROLYSIS IN THE SYSTEM «ACETONITRILE-WATER-DIMETHYLAMINE»
69
6.1. Preparation and application of the flavonoid amino derivatives
69
6.2. Electrolysis of eupafolin in the presence of dimethylamine
71
6.2.1 Cyclic voltammetry
72
6.2.2. Bulk electrolysis
74
7. ELECTROLYSIS IN THE SYSTEM «ETHANOL-WATER»
76
7.1. Anodic oxidation of the fisetin in the ethanol
76
7.2. Bulk electrolysis at the controlled potential
87
7.3. Proposed scheme for the fisetin transformations in an aqueous-ethanol solution under the conditions of anodic polarization
89
7.4. Possible schemes for the ethoxylation of flavonoids
91
CONCLUSIONS
100
REFERENCES
104

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