Naslov
Carbazole derivatives as precursors of aza-o- quinone methides

Autori
Draženović, Josip ; Škalamera, Đani ; Basarić, Nikola

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

Izvornik
28HSKIKI : 28th Croatian Meeting of Chemists and Chemical Engineers and 6th Symposium Vladimir Prelog : Book of Abstracts / Rogošić, Marko - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2023, 69-69

Skup
28. HSKIKI : 28th Croatian Meeting of Chemists and Chemical Engineers and 6th Symposium Vladimir Prelog

Mjesto i datum
Rovinj, Hrvatska, 28.03.2023. - 31.03.2023

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Aza-quinone methides ; Carbazoles ; Photochemistry

Sažetak
Aza- derivatives of quinone methides derivatives (a-QM) are well-known and relatively reactive intermediates. However, albeit, oxygen analogs are definitely more less represented in literature compared to oxygen analogs. [1] The use of a- QMAza-quinone methides (a-QM) are useful building blocks has been demonstrated inin the organic synthesis of various types of biologically important molecules such as hydroquinolines, indoles and benzotriazepines. Although a-QM these intermediates are most often prepared by the ground state reactions in the ground electronic state, there are a few examples where a-QM were generated by photochemically reactions. [2, 3] FurthermoreFor example, a-QM was prepared in a dehydration reaction of o-aminobenzyl alcohol. (o- ABA). Also, mentioned intermediate was detected by laser flash photolysis and trapped by several types of nucleophiles. [3] However, a-QMit’s trapping in [4+2] cycloaddition reactions was n'ot successfully trapped by alkenesdue to its intermolecular reactions in [4+2] cycloaddition reactions. [3] With the aim to develop novel classes of photoactivable anticancer drugs, we incorporated a- QM precursors in the carbazole derivatives. Carbazoles can be excited with near- visible light (>350 nm), and some of them have shown capability to non-covalently bind to polynucleotides. Herein we report synthesis of several carbazole a-QM precursors and investigation of their photochemical reactivity. derivatives that could be able to generate a-QM in photochemical reactions might be applicable in biological systems because of the possible intercalation of this planar system into biopolymers such as DNA or proteins. Because of that, we tried to prepare a few carbazolylphenyl derivatives of methanol (a derivative of p-ABA) and investigate the possibility of photochemical generation of a-QM from mentioned compounds. para- derivatives were successfully prepared by benzoylation of carbazole and reduction of the carbonyl group. Also, the photochemical reactivity was investigated by The irradiation experiments in methanol and isolation of methyl ether the photoproducts were isolated and fully characterized. ortho-derivatives demand more complex synthetic routes that include protection of para-position.(Scheme 1) is an indication for the photochemical generation of para-a-QM, which to date have not been formed photochemically.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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