Synthesis and characterisation of quaternary 10,11-dihydro derivatives of cinchonidine and cinchonine

U okviru ovog diplomskog rada opisana je priprava dva derivata Cinhona alkaloida: 10,11-dihidrocinhonina i 10,11-dihidrocinhonidina reakcijom katalitičke hidrogenacije komercijalno dostupnih cinhonina i cinhonidina. Dobiveni dihidro derivati su potom kvaternizirani različito supstituiranim benzilnim bromidima te je pripravljeno 16 novih spojeva. Spojevi se razlikuju po supstituentima na benzenskom prstenu benzilne skupine i svi sadrže jedan ili više atoma fluora (uključujući trifluormetilnu i trifluormetoksi-skupine) u meta i para položaju. Identifikacija i kontrola čistoće pripravljenih spojeva provedena je analitičkim postupcima koji uključuju IR i NMR (1H i 13C) spektroskopiju. Derivatima je također određeno specifično optičko zakretanje.The preparation of two alkaloid derivatives, 10,11-dihydrocinchonine and 10,11-dihydrocinchonidine, by catalytic hydrogenation of commercially available cinchonine and cinchonidine is described in this thesis. The resulting dihydro derivatives are then quaternized with various substituted benzyl bromides, and 16 new compounds were prepared. Substituents on the benzene ring of the benzyl moiety were changed from a fluorine atom to trifluoromethyl and trifluoromethoxy groups in meta and para positions. Identification and purity control of the prepared compounds was performed by analytical methods including IR and 1D and 2D NMR spectroscopy. The specific optical rotations were also determined for all synthesized pseudoenantiomers