Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola

master's thesis

• Title (english): Naphthoxazole synthesis by photochemical cyclisation of 4-styryloxazoles
• Author: Ante Zdrilić
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Ivana Šagud (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-07-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U ovom radu proučavane su fotokemijske reakcije ciklizacije sustava sličnih stilbenu gdje je jedna benzenska jezgra zamijenjena oksazolskim prstenom. Priređen je niz 4-(aril/heteroariletenil)oksazola 3-10, koji su sintetizirani Wittigovom reakcijom iz oksazol-4-karbaldehida (1) ili 2-metil-oksazol-4-karbaldehida (2) te odgovarajućih fosfonijevih soli. Aldehidi 1 i 2 dobiveni su redukcijom iz odgovarajućih oksazolskih estera, etil-4-oksazolkarboksilata i metil-2-metiloksazol-4-karboksilata. Derivati oksazola koji su sintetizirani su 4-(4-metoksistiril)oksazol (3), 4-(4-metilstiril)oksazol (4), 4-(2-cijanostiril)oksazol (5), 4-(4-nitrostiril)oksazol (6), 4-(4metoksistiril)-2-metiloksazol (7), 2-metil-4-(4-metilstiril)oksazol (8), 4-(2-cijanostiril)-2-metiloksazol (9) i 2-metil-4-(4-nitrostiril)oksazol (10). Fotokemijskom elektrociklizacijom 4-(aril/heteroariletenil)oksazola 3-10, dobiven je niz novih naftoksazola. Derivati 4-(aril/heteroariletenil)oksazola 3-10 podvrgnuti su fotokemijskim reakcijama ciklizacije, na 300 nm ili 350 nm u uvjetima s kisikom i jodom prisutnima u otopini toluena. Novi pročišćeni naftoksazolski derivati nafto[2,1-d]oksazol-6-karbonitril (13), 8-metilnafto[2,1-d]oksazol (14), 8-nitronafto[2,1-d]oksazol (15), 8-metilnafto[2,1-d]oksazol (16) i 2-metil-8-metilnafto[2,1-d]oksazol (17), kao i svi njihovi polazni spojevi 4-(aril/heteroariletenil)oksazoli 3-10 u potpunosti su okarakterizirani modernim spektroskopskim metodama (jednodimenzionalni i dvodimenzionalni NMR, UV/Vis i IR).

Abstract (english)

In this work photochemical cyclization reactions were studied for stilbene like systems, where one benzene ring is replaced by an oxazole ring. A series of 4-(aryl/heteroarylethenyl)oxazoles 3-10 was synthesized by Wittig reaction from the corresponding oxazole-4-carbaldehyde (1)/2-methyl-oxazole-4-carbaldehyde (2) and diverse phosphonium salts. Aldehydes 1 and 2 were obtained by reduction from the corresponding oxazole esters, ethyl-4-oxazolecarboxylate and methyl-2-methyloxazole-4-carboxylate. The synthesized oxazole derivatives are as follows, 4-(4-methoxystyryl)oxazole (3), 4-(4-methylstyryl)oxazole (4), 4-(2-cyanostyryl)oxazole (5), 4-(4-nitrostyryl)oxazole (6), 4-(4methoxystyryl)-2-methyloxazole (7), 2-methyl-4-(4-methylstyryl)oxazole (8), 4-(2-cyanostyryl)-2-methyloxazole (9) and 2-methyl-4-(4-nitrostyryl)oxazole (10). Photochemical electrocyclization reaction of 4-(aryl/heteroarylethenyl)oxazoles 3-10 gave a series of new naphthoxazoles. The reaction took place at 300 nm or 350 nm, in conditions with oxygen and iodine present, in toluene solution. New naphthoxazole derivatives that were purified are as follows, naphtho[2,1-d]oxazole-6-carbonitrile (13), 8-methylnaphtho[2,1-d]oxazole (14), 8-nitronaphtho[2,1-d]oxazole (15), 8-methylnaphtho[2,1-d]oxazole (16) and 2-methyl-8-methylnaphtho[2,1-d]oxazole (17). All of the new compounds were fully characterized by modern spectroscopic methods (one-dimensional and two-dimensional NMR, UV / Vis and IR).

• Keywords: naftoksazoli; stiril-4-oksazoli; fotociklizacija
• Keywords (english): naphthoxazoles; styryl-4-oxazoles; photocyclization
• Language: croatian
• URN:NBN: urn:nbn:hr:149:126333
• Study programme: Title: Environmental Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka ekoinženjerstva (magistar/magistra inženjer/inženjerka ekoinženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-04-22 09:03:58