Naslov
Electrochemical approach to new derivatives of 4H- 1,3-benzoxazines and 4H-1,3-benzothiazines with potential affinity for DNA/RNA

Autori
Kragol, Goran ; Kovačec, Petra ; Mlakić, Milena ; Škorić, Irena

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
23rd Tetrahedron Symposium / Russel, Angela ; Hu, Jinbo - Goteborg : University of Gothenburg, 2023

Skup
23rd Tetrahedron Symposium

Mjesto i datum
Göteborg, Švedska, 27.06.2023. - 30.06.2023

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
4H-1, 3-benzoxazines, 4H-1, 3-benzothiazines, amination, electrochemical synthesis

Sažetak
Fused heterocyclic skeletons like benzoxazines and benzothiazines are interesting molecular structures due to their potential pharmacological application.ref The goal of this work was to prepare a few specific arylamino-substituted derivatives of 4H-1, 3-benzoxazinium and 4H-1, 3- benzothiazinium salts in order to study their affinity to bind DNA/RNA. We decided to use synthetic route in which the key synthetic step is the intramolecular dehydrogenative coupling of N- benzylbenzamides and N- benzylbenzenecarbothioamides to form 4H-1, 3- benzoxazines and 4H-1, 3-benzothiazines, respectively. This approach was used because there was a possibility to employ the economical, fast, and environmentally friendly electrochemical synthetic approach in this step.ref Desired chloro-, dichloro-, and cyano-substituted N- benzylbenzamide and N-benzylbenzenecarbothioamide precursors were easily prepared in one and two synthetic steps. The initial conditions for electrochemical intramolecular dehydrogenative cyclization to prepare corresponding 4H-1, 3- benzoxazines and 4H-1, 3-benzothiazines were substantially optimized in order to achieve satisfactory yields. The optimization involved change of current or voltage, reagent concentration, temperature, time, and electrodes. The reaction kinetics were also followed indicating that it depends on the substitution of the precursors but it was quite fast in all cases. The following step of the synthesis was C-N coupling in which Buchwald-Hartwig method was used. The last step was formation of salt that was tried with 4H-1, 3-benzothiazine derivatives.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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