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V diplomskem delu so s ti. one-pot sintezno metodo predstavljene sinteze nekaterih 2H-piran-2-onskih derivatov. V postopku so potrebne spojine z aktiviranimi metilenskimi ali metilnimi skupinami, ki reagirajo v ustreznem topilu (acetanhidridu) z ustreznim C1 sintonom (npr. DMFDMA) ter N-acilglicinom. V organski kemiji imajo 2H-piran-2-oni velik pomen, saj služijo kot dieni pri Diels–Alderjevih reakcijah. Njihovi derivati so v organski kemiji zelo zanimivi, saj jih lahko uporabimo kot vsestranski gradniki pri sintezah ključnih intermediatov. Pri raziskovalnem delu sem naredila sinteze treh različnih 2H-piran-2-onov in sicer sintezo 5-acetil-3-benzoilamino-6-metil-2H-piran-2-ona, sintezo 3-benzoilamino-6-(2-tienil)-2H-piran-2-ona in sintezo 3-benzoilamino-6-fenil-2H-piran-2-ona. Pri sintezi biciklo[2.2.2]oktenskega derivata sem izhajala iz svojega 2H-piran-2-ona (3-benzoilamino-6-(2-tienil)-2H-piran-2-on) kot izhodnega diena. Kot alkenski dienofil sem uporabila maleinanhidrid in izvedla Diels–Alderjevo reakcijo ob prisotnosti tetralina (tetrahidronaftalen) kot topila. Vse nastale produkte sintez sem tudi ustrezno karakterizirala. In the Diploma Work, the synthesis of some 2H-pyran-2-one derivatives with the so-called one-pot synthesis method is presented. Compounds with activated methylene or methyl groups are required in this process. They react in a suitable solvent (acetic anhydride) with an appropriate C1 synthon (e.g. DMFDMA) and N-acylglycine. In organic chemistry, 2H-pyran-2-ones are of great importance because they serve as dienes in Diels–Alder reactions. Their derivatives are very interesting in organic chemistry because they can be used as versatile building blocks in the synthesis of key intermediates. In my research work, I carried out the synthesis of three different 2H-pyran-2-ones, i.e. the synthesis of 5-acetyl-3-benzoylamino-6-methyl-2H-pyran-2-one, the synthesis of 3-benzoylamino-6-(2-thienyl)-2H-pyran-2-one, and the synthesis of 3-benzoylamino-6-phenyl-2H-pyran-2-one. In the synthesis of the bicyclo[2.2.2]octene derivative, I proceeded from my 2H-pyran-2-one (3-benzoylamino-6-(2-thienyl)-2H-pyran-2-one) as the starting diene. I used maleic anhydride as an alkene dienophile and performed the Diels–Alder reaction in the presence of tetralin (tetrahydronaphthalene) as a solvent. I also characterized all the resulting syntheses products appropriately. |
