Oxidation reactions of cyclopent-2-en-1-yl thiophene derivatives

Yurii Klimko; Dmitrii Pisanenko; Iryna Koshchii; Igor Levandovskii

doi:10.15649/2346075X.3508

Authors

Yurii Klimko National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”
Dmitrii Pisanenko National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”
Iryna Koshchii National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”
Igor Levandovskii National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”

DOI:

https://doi.org/10.15649/2346075X.3508

Keywords:

Enamines, Antimicrobials, Epimers, Epoxidation, M-Chloroperbenzoic acid

Abstract

Introduction: Thiophene derivatives are common in a large number of natural compounds. In addition, their biological activity provides great opportunities for synthetic organic chemistry. In particular, cyclopentenylthiophenes have high antimicrobial activity, can affect various inflammatory mechanisms, and can be effective in the treatment of cancer. However, in research, it is essential to first learn how to obtain compounds in pure form and to select such synthesis conditions that, when scaled up and introduced into widespread production, the affordability and safety of the processes would meet the needs of both consumers and pharmaceutical companies. Material and Methods: As an oxidant, meta-chloroperoxybenzoic acid was used, which allowed exploring its oxidative properties and advantages of use in more detail. Results and Discussion: In the course of this work, several cyclopentenylthiophene derivatives were synthesised, the ratio of isomers in the synthesis of these compounds was analysed, and the advantages and disadvantages of the synthesis methods were discussed. On the other hand, there are several issues that require additional research, including the effect of temperature conditions, electrophilicity of substituents and other factors on the course of the epoxidation reaction for cyclopentenylthiophenes. Conclusion: The research of thiophene derivatives is relevant both from the standpoint of exploring electronic effects when substituents with different acceptor properties are introduced into the heterocyclic aromatic system and from the standpoint of medicinal chemistry, as they are interesting biologically active objects with high chemical stability, good penetration of cell membranes, ability to affect enzyme activity, bind to receptors.

Author Biographies

Yurii Klimko, National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”

Department of Organic Chemistry and Technology of Organic Compounds

Dmitrii Pisanenko, National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”

Department of Organic Chemistry and Technology of Organic Compounds

Iryna Koshchii, National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”

Department of Organic Chemistry and Technology of Organic Compounds

Igor Levandovskii, National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”

Department of Organic Chemistry and Technology of Organic Compounds

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