Preparation of n-heterocyc compounds by environmentally benign cascade reactions

Kolcsár Vanessza Judit and Szőllősi György: Preparation of n-heterocyc compounds by environmentally benign cascade reactions.

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The N-heterocyclic compounds include various molecules with significant biological activity, such as the quinazolinone derivatives. The preparation, characterization and application of these molecules are in the focus of pharmaceutical chemistry. The mono- and disubstitued dihidroquinazolinone derivatives are potential anti-cancer and anti-inflammatory compounds, besides they can be used as other pharmaceutical and agrochemical ingredients [1]. Nowadays the demand for the protection of the environment is fortunately increasing, which places numerous expectation on the industries. In the fine chemical and pharmaceutical processes, it has become a basic requirement to take into account the 12 principles of green chemistry. Due to this, the catalytic and neat reactions along with the application of compound from sustainable sources, environmentally friendly solvents and alternative activation methods have a great importance. Among the alternative energy transmission methods, it is worth to highlight the implementation of the mechanochemistry, as the reactions carried out in ball mills, have many of the above-mentioned advantages. In this present study, we examined the cascade reaction of anthranilamide and acetone, in which one ring-closing step occurs, and then we expanded the system to a bifunctional compound, ethyl levulinate, which is a renewable reaction partner, to achieve a second ring-closing step. We examined the possibilities of neat reactions, the quality of the applied catalyst, reaction temperature and time. After the successful optimization of the magnetically stirred neat reactions, we turned our focus to the mechanochemical activation of the reactions. It is possible to carry out several reactions neat in a ball mill, however generally better result can be achieved by adding a small amount of solvent to improve the mixing and the energy transition in the system [2]. Under the optimized conditions, the reactions were carried out with outstanding selectivity, and the final products were obtained in good yields. The developed method provides essential experiences to synthesize optically pure Nheterocycles in a system that meets today’s environmental expectations. The initial experiment of the reaction between anthranilamide and other bifunctional compounds was also carried out. It is our ongoing future goal to optimize the conventional, then the mechanochemical synthesis of optically pure condensed ring systems.

Item Type: Conference or Workshop Item
Journal or Publication Title: Proceedings of the International Symposium on Analytical and Environmental Problems
Date: 2021
Volume: 27
ISBN: 978-963-306-835-9
Page Range: pp. 171-176
Language: English
Publisher: University of Szeged
Place of Publication: Szeged
Event Title: International Symposium on Analytical and Environmental Problems (27.) (2021) (Szeged)
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Uncontrolled Keywords: Környezetkémia, Szerves kémia
Additional Information: Bibliogr.: p. 175-176. ; ill. ; összefoglalás angol nyelven
Subjects: 01. Natural sciences
01. Natural sciences > 01.04. Chemical sciences
Date Deposited: 2022. May. 31. 08:15
Last Modified: 2022. Aug. 08. 15:40

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