Elektrokemijska sinteza novih 1,3-benztiazinskih i 1,3-benzoksazinskih soli s potencijalnim afinitetom prema DNK/RNK

master's thesis

• Title (english): Electrochemical synthesis of new derivates of 4H-1,3-benzoxazine and 4H-1,3-benzothiazine salts with potential affinty for DNA/RNA
• Author: Petra Kovačec
• Mentor: Irena Škorić (mentor)
• Mentor: Goran Kragol (komentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Goran Kragol (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-08, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Klasičnoj sintezi organskih spojeva unazad nekoliko desetljeća pridružuje se elektroorganska sinteza. Ona pruža mogućnost ekonomične, brze i ekološki prihvatljive proizvodnje organskih spojeva. Derivati 4H-1,3-benzoksazina i 4H-1,3-benztiazina te njihove soli zanimljive su strukture zbog potencijalnog farmakološkog djelovanja. Neki od njih do danas su sintetizirani elektrokemijskom sintezom, a ovaj je rad svojevrsni nastavak sinteze novih, do sada, nesintetiziranih derivata. Također, optimizirani su uvjeti navedenih reakcija, te su uspješno dobiveni i izolirani spojevi 4a i 4a', 4c, 4d, 4e, 5a i 5a'. Sinteza spojeva 4b i 5b provedena je u svrhu ponavljanja do sada već provedene sinteze poradi usporedbe uvjeta reakcija s dobivenim rezultatima. Nadalje, provedeno je aminiranje odabranih derivata 4H-1,3-benzoksazina i 4H-1,3-benztiazina u svrhu pomaka UV-spektra u vidljivo područje. Uspješno su sintetizirani i izolirani spojevi 9,10a i 10b, 11, 12, i 13. Također je uspješno provedeno aminiranje N-(4-klorbenzil)benzamida koji ima u budućnosti potencijal prevođenja u ciklički oblik optimiziranjem uvjeta elektrokemijske ciklizacije. Svi su spojevi okarakterizirani 1H NMR metodom te je u svim dobivenim uzorcima detektirana očekivana masa tekućinskom kromatografijom vrlo visokog učinka vezane na spektrometar masa (eng. UPLC-MS/UV).

Abstract (english)

Electroorganic synthesis has been joining the classic synthesis of organic compounds for several decades. It provides the possibility of economical, fast and environmentally friendly production of organic compounds. Derivatives of 4H-1,3-benzoxazine and 4H-1,3-benzothiazine and their salts are interesting structures due to their potential pharmacological application. Some of them have been synthesized by electrochemical synthesis, and this work is the continuation of the synthesis of so far unsynthesized derivatives. Also, the conditions of the mentioned reactions were optimized, and compounds 4a and 4a', 4c, 4d, 4e, 5a and 5a' were successfully obtained and isolated. The synthesis of compounds 4b and 5b was carried out in order to repeat the synthesis already carried out so far in order to compare the reaction conditions with the obtained results. Furthermore, the amination of the selected derivatives 4H-1,3-benzoxazine and 4H-1,3-benzthiazine was carried out in order to shift the UV-spectrum into the visible region. Compounds 9, 10a and 10b, 11, 12, and 13 were successfully synthesized and isolated. The amination of N-(4-chlorobenzyl)benzamide, which has the potential to be converted into a cyclic form in the future by optimizing the conditions of electrochemical cyclization, was also successfully performed. All compounds were characterized by the 1H-NMR method, and the expected mass was detected in all obtained samples,by performing the high-performance liquid chromatography attached to a mass spectrometer (eng. UPLC-MS/UV).

• Keywords: 4H-1 3-benzoksazini; 4H-1 3-benztiazini; aminiranje; elektrokemijska sinteza
• Keywords (english): 4H-1 3-benzoxazines; 4H-1 3-benzothiazines; amination; electrochemical synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:149:655153
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-03-10 15:45:25