| Abstract | U cilju sinteze novih 2-furostilbenskih oksima provedeno je niz kemijskih reakcija; Wittigova reakcija, Vilsmeierovo formiliranje te prevođenje aldehida u oksim. Sintetizirani su oksimi sa tri različita supstituenta; cijano-, metoksi- te dimetilamino-. Iz polaznih aldehida i soli dobiveni su Wittigovi produkti (cis-1, trans-1, cis-2, trans-2 te trans-3). Cijano- i metoksi-derivati daju cis i trans Wittigove produkte, dok kod dimetilamino-derivata nastaje samo trans izomer. Dobiveni Wittigovi produkti korišteni su u reakciji Vilsmeierovog formiliranja u svrhu sinteze formilnih derivata. Nakon provedenog formiliranja, dobiveno je šest aldehida (cis-4, trans-4, cis-5, trans-5, cis-6 i trans-6). Svaki Wittigov produkt dao je po jedan aldehid, osim dimetilaminoaldehida. Iako je nakon provedene Wittigove reakcije kod dimetilamino-derivata nastao samo trans-3 izomer, prilikom provedbe Vilsmeierovog formiliranja trans-3 izomerizira te nastaju dva izomera; cis-6 i trans-6. Sintetizirani 2-karbaldehidi iskorišteni su za sintezu novih 2-furostilbenskih oksima. Svi dobiveni oksimi imaju vrlo bliske Rf vrijednosti te ih je bilo potrebno pročistiti pomoću preparativnih TLC ploča, nakon čega je dobiveno 12 novih 2-furostilbenskih oksima, od kojih su cis,syn-7, cis,anti-7, trans,syn-7 te trans,anti-7 izolirani kao čisti spojevi, dok su spojevi cis,syn-8, cis,anti-8, trans,syn-8, trans,anti-8, cis,syn-9, cis,anti-9, trans,syn-9 te trans,anti-9 i nakon pročišćavanja na preparativnim TLC pločama ostali u smjesi. Svi sintetizirani spojevi okarakterizirani su spektroskopskim metodama; jednodimenzionalnim 1H i 13C NMR tehnikama. |
| Abstract (english) | In order to synthesize new 2-furostilbene oximes, a series of chemical reactions were carried out; Wittig reaction, Wilsmeier formulation and conversion of aldehyde to oxime. Oximes with three different substituents were synthesized; cyano-, methoxy- and dimethylamino-. Wittig products (cis-1, trans-1, cis-2, trans-2 and trans-3) were obtained from the starting aldehydes and salts. Cyano- and methoxy-derivatives give cis and trans Wittig products, while in dimethylamino-derivatives only the trans isomer is formed. The obtained Wittig products were used in the Vilsmeier formylation reaction for the synthesis of formyl derivatives. After formulation, six aldehydes were obtained (cis-4, trans-4, cis-5, trans-5, cis-6 and trans-6). Each Wittig product gave one aldehyde, except dimethylaminoaldehyde. Although only the trans-3 isomer was formed in the dimethylamino derivative after the Wittig reaction, during the implementation of Vilsmeier's formulation the trans-3 isomerized to form two isomers; cis-6 and trans-6. The synthesized 2-carbaldehydes were used for the synthesis of new 2-furostilbene oximes. All the obtained oximes have very close Rf values and it was necessary to purify them using preparative TLC plates, after which 12 new 2-furostilbene oximes were obtained, of which cis,syn-7, cis,anti-7, trans,syn-7 and trans, anti-7 isolated as pure compounds, while compounds cis,syn-8, cis,anti-8, trans,syn-8, trans,anti-8, cis,syn-9, cis,anti-9, trans,syn-9 and trans,anti-9 and after purification on preparative TLC plates remained in the mixture. All synthesized compounds were characterized by spectroscopic methods one dimensional 1H and 13C NMR techniques. |
