20.500.12556/RUL-171725 Sinteza in pretvorbe izbranih (aza)kinolizinilaminov Synthesis and transformations of selected (aza)quinolizinylamines V diplomskem delu sem v prvi stopnji sinteze s ciklokondenzacijo dveh različnih derivatov piridina spojini 1a in 1b in enaminona 2 pripravila dva kinolizinska derivata z zaščiteno amino skupino 3a in 3b. V drugi stopnji sinteze sem odstranila zaščitni skupini, pri čemer sta nastali spojini 3-amino-4H-piridino[1,2-a]pirimidin-4-on (4a) in 3-amino-1-ciano-4H-kinolizin-4-on (4b-HBr). Amina 4 sem v nadaljevanju pretvorila v ustrezna azida 5a in 5b z uporabo NaNO2 in NaN3. V zadnji stopnji sem na azida 5a in 5b s CuAAC “klik” reakcijo pripela alkil 4-fluorofenilacetilen (6), pri tem se je tvoril triazolski obroč. Tako sem pripravila dve, v literaturi doslej še ne znani spojini, 3-[4-(4-fluorofenil)-1H-1,2,3-triazol-1-il]-4H-pirido[1,2-a]pirimidin-4-on (7a) in 3-[4-(4-fluorofenil)-1H-1,2,3-triazol-1-il]-1-ciano-4H-kinolizin-4-on (7b). In this bachelor thesis I first prepared two different quinolizine derivatives with a protected amino group 3a and 3b through cyclocondensation of two pyridine derivatives 1a and 1b with enaminone 2. In the second step, I removed the protecting group to obtain 3-amino-4H-pyrido[1,2-a]pyrimidin-4-one (4a) and 3-amino-1-cyano-4H-quinolizine-4-one (4b-HBr). The amines 4 were then transformed into the corresponding azides 5a and 5b using NaNO2 and NaN3. In the final step, I performed a CuAAC “click” reaction between the azides 5a and 5b and 4-fluorophenylacetylene (6), which resulted in triazole ring formation to obtain two previously unknown compounds, 3-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl]-4H-pyrido[1,2-a]pyrimidin-4-one (7a) and 3-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1-cyano-4H-quinolizine-4-one (7b). enaminon ciklokondenzacija kinolizin azid “klik” reakcija triazol enaminone cyclocondensation quinolizine azide “click” reaction triazole true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2025-09-01 10:10:01 2025-09-01 10:10:07 2025-09-12 10:48:08 0000-00-00 00:00:00 2025 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 25805 248742147 Dolenc_Nitja_-_Sinteza_in_pretvorbe_izbranih_(aza)kinolizinilaminov.pdf Dolenc_Nitja_-_Sinteza_in_pretvorbe_izbranih_(aza)kinolizinilaminov.pdf 1 2E9F293F24A6092432B6FF96AE57B985 e2dc90185d767f61bd8f29c534674fa0bf658dc6c1a08052bac86bf807e8274a eefd96e7-870a-11f0-9328-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=215106 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0