Synthesis of amino derivatives of naphthoxazoles by photochemical cyclization

U svrhu mogućeg poboljšanja kvalitete života ljudima oboljelim od Alzheimerove bolesti proučavani su novi amino-derivati oksazola. U cilju proučavanja fotokemijskog ponašanja oksazolskih derivata razvijena je sinteza amino-derivata (nafto)oksazola (a-e). Sinteza je provedena nukleofilnom aromatskom supstitucijom slijedeći Buchwald-Hartwigovu reakciju aminacije te uzastopnim fotokemijskim elektrocikličkim zatvaranjem amino-supstituiranih produkata. Novonastali spojevi pokazali su potencijalnu farmakološku aktivnost zbog prisutnosti oksazolske jezgre kao i amino-skupine. Dobiveni spojevi pročišćeni su kromatografskim metodama koristeći tankoslojnu i kolonsku kromatografiju. Spojevi su uspješno izolirani i okarakterizirani spektroskopskim metodama. Prilikom izrade ovoga diplomskog rada nastali fotoprodukti su N-benzilnafto[1,2-d]oksazol-8-amin (a), N-(4-fluorbenzil)nafto[1,2-d]oksazol-8-amin (b), N-(tiofen-2-ilmetil)nafto[1,2-d]oksazol-8-amin (c), nafto[1,2-d]oksazol-8-amin (d), (E)-4-(2-(oksazol-5-il)vinil)anilin (e) i (Z)-4-(2-(oksazol-5-il)vinil)-N-(tiofen-2-ilmetil)anilin (f).New derivatives of amino-naphthoxazole have been investigated to improve the quality of life for people with Alzheimer's disease. For the purpose of studying the photochemical behavior of oxazole derivatives, a synthesis of amino derivatives od (naphtho)oxazole (a-f) was developed. The synthesis was carried out by nucleophilic aromatic substitution, the Buchwald-Hartwig amination reaction followed by photochemical illumination of amino-substituted products. The newly formed compounds showed potential pharmacological activity due to the presence of the oxazole ring as well as the amino group. The resulting compounds were purified by chromatographic methods using thin layer and column chromatography. The compounds were successfully isolated and characterized by spectroscopic methods. In this master thesis, the resulting photoproducts are N-benzylnaphtho[1,2-d]oxazole-8-amine (a), N-(4-fluorobenzyl)naphtho[1,2-d]oxazole-8-amine (b), N-(tiophen-2-ylmethyl)naphtho[1,2-d]oxazole-8-amine (c), naphtho[1,2-d]oxazole-8-amine (d), (E)-4-(2-(oxazol-5-yl)vinyl)aniline (e) and i (Z)-4-(2-(oxazol-5-yl)vinyl)-N-(tiophen-2-ylmethyl)aniline (f)