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undergraduate thesis
Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. urn:nbn:hr:149:636247
Kos, Marija
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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Kos, M. (2018). Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:636247

Kos, Marija. "Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:636247

Kos, Marija. "Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:636247

Kos, M. (2018). 'Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:636247

Kos M. Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2018 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:636247

M. Kos, "Sinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:149:636247

Metadata
TitleSinteza i spektroskopska karakterizacija amido-supstituiranih pentacikličkih derivata benzimidazola
Title (english)Synthesis and spectroscopic characterization of amido substituted pentacyclic benzimidazole derivatives
AuthorMarija Kos
MentorMarijana Hranjec (mentor)
Committee memberMarijana Hranjec (predsjednik povjerenstva)
Committee memberNataša Perin (član povjerenstva)
Committee memberMirjana Novak Stankov (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2018-09-11, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U okviru ovog rada provedena je sinteza amido supstituiranih pentacikličkih derivata benzimidazola pri čemu su novi spojevi priređeni klasičnim reakcijama organske i fotokemijske sinteze. Aciklički prekursori 3 i 11 dobiveni su reakcijom kondenzacije 2-cijanometilbenzimidazola 2 s kinolinkarbaldehidima 1 i 10. U sljedećem stupnju sinteze provedene su ciklizacije kako bi se dobili glavni ciklički prekursori za ciljane derivate benzo[g]benzo[4,5]imidazo[1,2-a][1,8]naftiridina te benzo[g]benzo[4,5]imidazo[1,2-a][1,5]naftiridina. Spoj 4 dobiven je termičkom ciklizacijom u sulfolanu iz spoja 3 dok je spoj 12 priređen iz prekursora 11 fotokemijskom ciklizacijom osvjetljavanjem UV-Hg lampom od 400 W. Nadalje su iz cijano derivata 4 i 12 kiselo kataliziranom hidrolizom priređene odgovarajuće kiseline 5 i 13 koje su u reakciji s tionil-kloridom dale acilne kloride 6 te 14. Tretiranjem s aminima uz suhi diklormetan iz acilnih klorida 6 i 14, u završnom su koraku sintetizirani ciljani produkti 7-9 te 15. Spoj 15 dobiven je i provođenjem „one pot“ sinteze direktno iz kiseline 13 uz male količine katalizatora DMF-a, tionil-klorid, toluen te izobutilamin. Dodatkom veće količine DMF-a dobiven je produkt 16. Strukture priređenih produkata potvrđene su 1H i 13C NMR spektroskopijom, a uz to neki su spojevi okarakterizirani UV/Vis spektroskopijom te masenom spektrometrijom.
Abstract (english)
This work presents the synthesis and spectroscopic characterization of amido substituted pentacyclic benzimidazole derivates whereby the new compounds were prepared by conventional reactions of organic and photochemical synthesis. Acyclic precursors 3 and 11 were prepared by the condensation reaction of 2-cyanomethylbenzimidazole 2 with quinolinecarboxaldehydes 1 and 10. In the next stage of synthesis, cyclization reactions were carried out in order to get the main cyclic precursors for target derivates benzo[g]benzo[4,5]imidazo[1,2-a][1,8]naphthyridine and benzo[g]benzo[4,5]imidazo[1,2-a][1,5]naphthyridine. Precursor 4 was prepared by the thermal cyclization in sulfolane from precursor 3 while 12 was prepared from 11 by photochemical cyclization reaction with UV-Hg lamp of 400 W. Further more, from cyano derivates 4 and 12 corresponding acids 5 and 13 were prepared by acid catalysed hydrolysis. Carboxylic acids 5 and 13 gave in the next step, in reaction with thionyl-chloride, acyl chlorides 6 and 14. Treating acyl chlorides 6 and 14 with corresponding amines in dry dichloromethane were synthesized targeted products 7-9 and 15. Compound 15 was also prepared by „one pot“ synthesis directly from carboxyl acid 13 and with small amount of DMF, thionyl-chloride, toluene and isobutylamine. By adding more DMF, product 16 was obtained. The structures of prepared compounds were confirmed by means of 1H and 13C NMR, also some of them were characterized by UV/Vis spectroscopy and mass spectrometry.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:636247
Study programmeTitle: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: undergraduate
Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
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Created on2021-11-22 11:34:23