20.500.12556/RUL-171960 Sinteza različnih 5,6-disubstituiranih 3-acilamino-2H-piran-2-onov in nadaljnje transformacije Synthesis of various 5,6-disubstituted 3-acylamino-2H-pyran-2-ones and further transformations V diplomskem delu se ukvarjam s sintezo različnih 5,6-disubstituiranih 2H-piran-2-onov. Izhodišče načrtovanja kemijskih reakcij je "one-pot" sintezna metoda po Kepetu in njene kasnejše modifikacije. Za izhodne spojine sem uporabil različne aktivirane elektrofile, 1,3-diketone ter cikloalkanone. Reagiral sem jih s hipurno kislino v vlogi N-acilglicina ter DMFDMA kot C1-sintonom. Uspešno sem pripravil dva analoga, mono- in biciklični 5,6-disubstituiran 3-benzoilamino-2H-piran-2-on. Kot nadaljnjo transformacijo sem raziskoval najprej odščito 3-acilaminske skupine z vročo kislinsko hidrolizo amidne vezi. Z dobrim izkoristkom sem uspešno izoliral 3-aminski analog. Na dobljeni produkt sem poizkusil uvesti novo zaščitno skupino z akriloil kloridom. 2H-piran-2-oni in njihovi derivati lahko služijo kot ogrodje pomembnih biološko aktivnih molekul, ki so ključne v razvoju medicinske kemije in novih zdravil. In this thesis, I focus on the synthesis of various 5,6-disubstituted 2H-pyran-2-ones. The starting point for the design of the synthesis is the one-pot synthetic method according to Kepe and its later modifications. For the starting compounds, I used various activated electrophiles, 1,3-diketones, and cycloalkanones. I reacted them with hippuric acid as the N-acylglycine and DMFDMA as the C1-synthon. I successfully prepared two analogues: a mono- and a bicyclic 5,6-disubstituted 3-benzoylamino-2H-pyran-2-one. As a further transformation, I first investigated the removal of the 3-acylamino group by hot acid hydrolysis of the amide bond. The 3-amino analogue was successfully isolated with a good yield. On the same product, I attempted to introduce a new protecting group with acryloyl chloride. 2H-pyran-2-ones and their derivatives can serve as scaffolds of important biologically active molecules that are crucial in the development of medicinal chemistry and new drugs. cikloadicija 2H-piran-2-on N-acilglicin "one-pot" sinteza kislinska hidroliza cycloaddition 2H-pyran-2-one N-acylglycine one-pot synthesis acid hydrolysis true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2025-09-04 13:45:01 2025-09-04 13:45:06 2025-10-16 13:19:30 0000-00-00 00:00:00 2025 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 25553 253491715 Derganc_Drejc_aron_-_Sinteza_razlicnih_5,6-disubstituiranih_3-acilamino-2H-piran-2-onov_in_nadal.pdf Derganc_Drejc_aron_-_Sinteza_razlicnih_5,6-disubstituiranih_3-acilamino-2H-piran-2-onov_in_nadal.pdf 1 E44CFDB127662581E3D319D550AA09E3 3a02a5c09a2f4f158d00aadf6f44dbf60f8c6fa7cd21ee5c4eee56e75b6f7de3 740a3e72-8984-11f0-9328-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=215576 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0