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master's thesis
Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. urn:nbn:hr:149:126333
Zdrilić, Ante
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Zdrilić, A. (2017). Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:126333

Zdrilić, Ante. "Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:126333

Zdrilić, Ante. "Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:126333

Zdrilić, A. (2017). 'Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:126333

Zdrilić A. Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2017 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:126333

A. Zdrilić, "Sinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2017. Available at: https://urn.nsk.hr/urn:nbn:hr:149:126333

Metadata
TitleSinteza naftoksazola fotokemijskom ciklizacijom 4-stiriloksazola
Title (english)Naphthoxazole synthesis by photochemical cyclisation of 4-styryloxazoles
AuthorAnte Zdrilić
MentorIrena Škorić (mentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberIvana Šagud (član povjerenstva)
Committee memberLidija Furač (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2017-07-14, 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
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:126333
Study programmeTitle: 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 resourceText
File originBorn digital
Access conditionsOpen access
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Created on2020-04-22 09:03:58