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master's thesis
Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. urn:nbn:hr:149:493332
Boček, Ida
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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Boček, I. (2017). Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:493332

Boček, Ida. "Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:493332

Boček, Ida. "Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:493332

Boček, I. (2017). 'Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:493332

Boček I. Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina [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:149:493332

I. Boček, "Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2017. Available at: https://urn.nsk.hr/urn:nbn:hr:149:493332

Metadata
TitleSinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina
Title (english)Synthesis and spectroscopic characterization of novel amino-substituted tetracyclic imidazo[4,5-b]piridyne derivatives
AuthorIda Boček
MentorMarijana Hranjec (mentor)
Committee memberMarijana Hranjec (predsjednik povjerenstva)
Committee memberNataša Perin (član povjerenstva)
Committee memberDragana Mutavdžić Pavlović (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2017-07-07, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U ovom radu prikazana je sinteza i spektroskopska karakterizacija novih amino supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina. Brojna istaživanja pokazala su da derivati imidazo[4,5-b]piridina imaju širok spektar biološkog djelovanja, a upravo tetraciklički derivati pokazali su antitumorsko djelovanje. Za pripravu ciljanih molekula korištene su klasične metode organske kemije, dok je posljednji stupanj sinteze potpomognut mikrovalnim zračanjem. Kondenzacijom derivata imidazo[4,5-b]piridina 3 s 2-klorbenzoil-kloridom ili 4-fluor- 2-klorbenzoil-kloridom, priređeni su aciklički prekursori 5 i 19. Termičkom ciklizacijom priređena je smjesa cikličkih regioizomera 6a i 6b te 20a i 20b iz kojih su dobiveni 5-klor supstituirani tetraciklički derivati 9 i 10 te 2-fluor-5-klor supstituirani derivati 21 i 22. Amino i diamino supstituirani regioizomeri 9-16 i 24-28 i 30 priređeni su nekataliziranom reakcijom aminacije potpomognutom mikrovalovima. Strukture priređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom, a struktura regioizomera utvrđena je 2D NMR spektroskopskim tehnikama. Odabrani derivati 11, 15, 25 i 29 okarakterizirani su UV/Vis i fluorimetrijskom spektroskopijom.
Abstract (english)
Within this work, the synthesis and spectroscopic characterization of novel aminosubstituted tetracyclic imidazo[4,5-b]pyridine derivatives was presented. According to previous research, imidazo[4,5-b]pyridine derivatives have a broad spectrum of biological activities and tetracyclic derivatives showed potent antitumour activity. For the synthesis of novel targeted compounds, classical organic synthesis reactions as well as microwave assisted synthesis were used. Due to the condensation of imidazo[4,5-b]pyridine derivative with 2-chlorobenzoyl chloride or 4-fluoro-2-chlorobenzoyl chloride, acyclic precursors 5 and 19 were prepared. In reaction of termic cyclization, the mixture of cyclic regioisomers 6a and 6b or 20a and 20b was prepared. Furthermore, from 6a and 6b, or 20a and 20b, 5-chloro (7 and 8) and 2-fluoro- 5-chloro- (21 and 22) substituted tetracyclic derivatives were obtained in the next step. Amino substituted 9 – 16 and diamino substituted 24 – 28 and 30 regioisomers were prepared by uncatalyzed microwave assisted amination. Structures of newly prepared compounds were confirmed by means of 1H and 13C NMR spectroscopy. Structure of regioisomers was determined by 2D NMR spectroscopy. Spectroscopic characterization of derivatives 11, 15, 25 and 29 was performed by using UV/Vis and fluorimetric spectroscopy in methanol.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:493332
Study programmeTitle: Applied Chemistry - Graduate 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: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2019-10-02 14:17:37