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Sinteza različnih 5,6-disubstituiranih 3-acilamino-2H-piran-2-onov in nadaljnje transformacije
ID Derganc, Drejc Aron (Author), ID Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Abstract
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.

Language:Slovenian
Keywords:cikloadicija, 2H-piran-2-on, N-acilglicin, "one-pot" sinteza, kislinska hidroliza
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2025
PID:20.500.12556/RUL-171960 This link opens in a new window
COBISS.SI-ID:253491715 This link opens in a new window
Publication date in RUL:04.09.2025
Views:390
Downloads:123
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Secondary language

Language:English
Title:Synthesis of various 5,6-disubstituted 3-acylamino-2H-pyran-2-ones and further transformations
Abstract:
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.

Keywords:cycloaddition, 2H-pyran-2-one, N-acylglycine, one-pot synthesis, acid hydrolysis

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