scholarly journals Efficient access to aliphatic esters by photocatalyzed alkoxycarbonylation of alkenes with alkyloxalyl chlorides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Jian-Qiang Chen ◽  
Xiaodong Tu ◽  
Qi Tang ◽  
Ke Li ◽  
Liang Xu ◽  
...  
Keyword(s):  
Natural Product ◽  
Oxalyl Chloride ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Formal Synthesis ◽  
Efficient Access ◽  
Wide Range ◽  
Aliphatic Esters

AbstractAliphatic esters are essential constituents of biologically active compounds and versatile chemical intermediates for the synthesis of drugs. However, their preparation from readily available olefins remains challenging. Here, we report a strategy to access aliphatic esters from olefins through a photocatalyzed alkoxycarbonylation reaction. Alkyloxalyl chlorides, generated in situ from the corresponding alcohols and oxalyl chloride, are engaged as alkoxycarbonyl radical fragments under photoredox catalysis. This transformation tolerates a broad scope of electron-rich and electron-deficient olefins and provides the corresponding β-chloro esters in good yields. Additionally, a formal β-selective alkene alkoxycarbonylation is developed. Moreover, a variety of oxindole-3-acetates and furoindolines are prepared in good to excellent yields. A more concise formal synthesis of (±)-physovenine is accomplished as well. With these strategies, a wide range of natural-product-derived olefins and alkyloxalyl chlorides are also successfully employed.

Efficient Access to Aliphatic Esters by Photocatalyzed Alkoxycarbonylation of Alkenes

2021 ◽  
Author(s):  
Jian-Qiang Chen ◽  
Xiaodong Tu ◽  
Qi Tang ◽  
Ke Li ◽  
Liang Xu ◽  
...  
Keyword(s):  
Natural Product ◽  
Oxalyl Chloride ◽  
Biologically Active ◽  
Formal Synthesis ◽  
Efficient Access ◽  
Wide Range ◽  
New Strategy ◽  
Aliphatic Esters ◽  
First Time

Abstract Aliphatic esters are essential constituents of biologically active compounds and versatile chemical intermediates for the synthesis of drugs. However, their preparation from readily available olefins remains challenging. In this report, a new strategy to access aliphatic esters from olefins through a unique photocatalyzed alkoxycarbonylation reaction is described. Alkyloxalyl chlorides, generated in situ from the corresponding alcohols and oxalyl chloride, are engaged for the first time as alkoxycarbonyl radical fragments under photoredox catalysis. This transformation tolerates a broad scope of electron-rich and electron-deficient olefins and provides the corresponding β-chloro esters in good yields. Additionally, a formal β-selective alkene alkoxycarbonylation is developed. And, a variety of oxindole-3-acetates and furoindolines are prepared in good to excellent yields. A more concise formal synthesis of (±)-physovenine is accomplished as well. With these strategies, a wide range of natural-product-derived olefins and alkyloxalyl chlorides are also successfully employed.

Chemical modification and Physicochemical properties of new derivatives 5-(thiophen-3-ilmethyl)-4-R1-1,2,4-triazole-3-thiol

2021 ◽  
pp. 4621-4629
Author(s):  
O.A. Bihdan ◽  
V.V. Parchenko
Keyword(s):  
Physicochemical Properties ◽  
High Reactivity ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Triazole Derivatives ◽  
Pharmaceutical Ingredients ◽  
Current Trends ◽  
Wide Range ◽  
Derivatives Of

Current trends in the search for new biologically active compounds among synthetic molecules have arguably proved a priority in studies of the heterocyclic 1,2,4-triazole system. For many years, 1,2,4-triazole derivatives remain the object of close attention of scientists of various scientific fields. The unique properties of 1,2,4-triazole derivatives include high reactivity, which allows different modification of this system, practical absence of toxicity of these derivatives and the presence of a wide range of biological, pharmacological properties, which in the complex provides the prerequisites for the creation of new biologically active compounds, and in the future, active pharmaceutical ingredients (AFI). The aim of our work is to investigate some transformations in a number of derivatives of 5-(thiophen-3-ylmethyl) -4-R1-1,2,4-triazole-3-thiol, to study the physicochemical properties of the new synthesized compounds. A well-known fact remains the successful attempt of many scientists involved in the study of the heterocyclic 1,2,4-triazole system to synthesize potential biologically active compounds. The process of creating new molecules is very painstaking and requires considerable effort. The chemical approaches for the synthesis of the starting compounds required for further transformations are well known and described. Therefore, we used the corresponding N-R1-2 as intermediates for the synthesis of new 5-(thiophen-3-ylmethyl) -4-R1-1,2,4-triazole-3-thiols appropriate ones were used N-R1-2-(2-(thiophen-3-yl) acetyl) hydrazinocarbothioamide.

Minor enantiomer recycling – a strategy to improve enantioselectivity

2016 ◽  
Vol 88 (4) ◽  
pp. 309-316 ◽  
Author(s):  
Christina Moberg
Keyword(s):  
Catalytic Reaction ◽  
Enantiomeric Purity ◽  
Biologically Active Compounds ◽  
Starting Material ◽  
Biologically Active ◽  
Active Compounds ◽  
Enantioselective Reactions

AbstractIn enantioselective reactions, the major, desired enantiomer is commonly obtained along with the minor, undesired enantiomer. By continuous recycling of this undesired enantiomer back to starting material, products with improved enantiomeric purity can be obtained. Such in situ minor enantiomer recycling can be accomplished by coupling the catalytic reaction to an exergonic transformation of a sacrificial reagent. The method has been applied to the synthesis of O-acylated cyanohydrins, which serve as starting materials for a variety of biologically active compounds.

scholarly journals Tale of Breslow Intermediate, a Central Player in N-Heterocyclic Carbene Organocatalysis: Then and Now

2021 ◽  
Author(s):  
Raghavan B. Sunoj ◽  
Monika Pareek ◽  
Yernaidu Reddi
Keyword(s):  
Natural Products ◽  
Heterocyclic Carbenes ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Wide Range

N-heterocyclic carbenes (NHCs) belong to the popular family of organocatalysts used in a wide range of reactions, including that for the synthesis of complex natural products and biologically active compounds....

scholarly journals INFLUENCE OF BIOTECHNOLOGICAL FACTORS ON THE YIELD OF BIOLOGICALLY ACTIVE COMPOUNDS FROM SORBUS AUCUPARIA

2021 ◽  
pp. 291-300
Author(s):  
Elena Nikolaevna Sokolova ◽  
Tat'yana Vladimirovna Yuraskina ◽  
Yuliya Aleksandrovna Borshcheva ◽  
Natal'ya Aleksandrovna Fursova ◽  
Anton Yur'yevich Sharikov ◽  
...  
Keyword(s):  
Amino Acids ◽  
Biologically Active Compounds ◽  
Biologically Active Substances ◽  
Biologically Active ◽  
Theoretical Research ◽  
Sorbus Aucuparia ◽  
Plant Materials ◽  
Active Compounds ◽  
Wide Range ◽  
Active Substances

Currently, the diet of almost all population groups in Russia is characterized by a deficiency of vitamins, essential amino acids, macro- and micronutrients, as well as biologically active substances (flavonoids, carotenoids, etc.). Replenishment of the lack of these components in the diet of the population due to natural sources of plant origin is an important and actual task of national health care. The rational use of natural components of plant materials containing a wide range of natural biologically active substances using biocatalytic methods, as well as the selection of optimal conditions for obtaining commodity forms of ingredients, will allow to create preventive products that have a beneficial effect on the human body. Theoretical research in the field of promising sources of food and biologically active ingredients among wild species of plant materials were carried out. Biomedical properties of Sorbus aucuparia were described. The technological characteristics of the biologically active substances extraction from dried plant raw materials was investigated. Thus, it was revealed that the degree of dried berries grinding about 0.2–0.8 mm, the hydromodule 1 : 10 and the extraction duration 240 minutes are most effective for the extractive substances yield. The enzymatic complex, allowing the maximum to release biologically valuable components to extract was selected. The amino acid composition of rowanberry with the use of high-performance liquid chromatography was investigated. Produced fermentalizates contain complex of biologically active compounds, including amino acids, vitamins, carotenoids, phenolic substances, that makes these ingredients promising for creation of various foodstuffs to improve quality, nutritional and biological value, taste and other consumer properties.

Efficient C(sp3)–H Bond Arylation of Tetrahydroisoquinolines with Knochel-Type Arylzinc Reagents under Oxidative Conditions

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1835-1839 ◽  
Author(s):  
Zhihua Peng ◽  
Zhi Yu ◽  
Dong-Huang Chen ◽  
Shuyuan Liang ◽  
Liwei Zhang ◽  
...  
Keyword(s):  
Functional Groups ◽  
Ester Group ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Wide Range

A novel C(sp3)–H bond arylation of tetrahydroisoquinoline (THIQ) derivatives with Knochel-type arylzinc reagents has been developed. In the presence of MgCl2, arylzinc reagents readily reacted with THIQ derivatives under oxidative conditions, affording a wide range of potentially biologically active compounds in good yields. Moreover, the developed method can tolerate a variety of sensitive functional groups such as an ester group.

scholarly journals Isolation and characterization of culturable actinobacteria associated with Polytrichum strictum (Galindez Island, the maritime Antarctic)

2021 ◽  
pp. 82-97
Author(s):  
O. Gromyko ◽  
◽  
S. Tistechok ◽  
I. Roman ◽  
O. Aravitska ◽  
...  
Keyword(s):  
Multidrug Resistant ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Rrna Gene ◽  
Biosynthetic Genes ◽  
Active Compounds ◽  
Isolation And Characterization ◽  
Polytrichum Strictum ◽  
Wide Range ◽  
Direct Inoculation

The main objective of the study is the evaluation of the diversity of actinobacteria associated with Polytrichum strictum — dominant species of widespread Antarctic Тall moss turf subformation and their characteristics as the producers of biologically active compounds. The actinobacterial isolates were isolated by direct inoculation, phenol pretreatment, and heated treatment. The cultural properties of the isolates were evaluated using diagnostic media. The antimicrobial activity of the isolates was determined by the point inoculations method. The phylogenetic analysis was based on sequence analysis of the 16S rRNA gene. The biosynthetic genes screening was performed using polymerase chain reaction. A total of 23 actinobacterial isolates associated with P. strictum were isolated, the four identified genera being Streptomyces (7 isolates), Micromonospora (14 isolates), Kribbella (1 isolate), and Micrococcus (1 isolate). Eight psychrotrophic strains of all identified genera were identified. The optimal pH values for all isolates were in the range 6–10. Four isolates grew on the medium with 7.5% NaCl. A significant number of the isolates showed a wide range of enzymatic activities. Antagonists of a wide range of pathogenic microorganisms were found, including against multidrug-resistant strain of Candida albicans and Methicillin-resistant Staphylococcus aureus. Some strains were active against phytopathogenic bacteria, namely three strains against Erwinia amylovora, one strain against Agrobacterium tumefaciens, and one strain against Pectobacterium carotovorum. More than half of the isolates showed antifungal activity against Fusarium oxysporum and Aspergillus niger. The biosynthetic genes involved in synthesizing a wide range of bioactive compounds were found in more than 80% of isolates. Antarctic actinobacteria isolated in this study demonstrate potential as the producers of a wide range of biologically active compounds. Further studies of these actinobacteria may lead to the identification of previously unknown biologically active compounds.

Copper-catalyzed N-arylation of pyrroles: An overview

2021 ◽  
Author(s):  
Kalathingal Nasreen Hisana ◽  
C. M. A. Afsina ◽  
Gopinathan Anilkumar
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Wide Range

N-Arylated pyrroles have a wide range of applications in pharmaceuticals, agrochemical industry and organic synthesis. They are intermediates for the formation of many biologically active compounds and natural products. Over...

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