Sinteza amidino-supstituiranih benzotiazola

undergraduate thesis

• Title (english): Synthesis of amidino-substituted benzothiazoles
• Author: Anja Ravlić
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Mirjana Novak Stankov (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-18, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Tema završnog rada je sinteza novih amidino supstituiranih derivata benzotiazola 8-10 i 16. Za pripravu ciljnih spojeva korištene su klasične metode organske sinteze. Sinteza je provedena s dva različita početna spoja: 4-kloranilina i 4-aminobenzonitrila. Sinteza amidino derivata 8-10 provedena je u pet stupnjeva zatvaranja, otvaranja benzotiazola, nukleofilne supstitucije bromacetonitrila i Pinnerove reakcije kojom su dobiveni ciljni spojevi
2-(4-(5-klor-benzotiazol-2-il)fenoksi)acetimidamid 8 i
5-klor-2-(4-((4,5-dihidro-1H-imidazol-2-il)metoksi)fenil)benzotiazol 9, dok sinteza spoja 10 nije bila uspješna. Sinteza 6-amidino supstituiranog benzotiazola provedena je u 4 stupnja koja su uključivala reakcije supstitucije 4-aminobenzonitrila i kalijeva tiocijanata, konverziju tiocijanatne skupine u tiolnu skupinu, zatvaranja benzotiazolnog prstena i Pinnerovu reakciju kojom nije dobiven ciljni spoj 16. Tijek Pinnerovih reakcija kojima se cijano skupina prevodi u amidinsku praćen je IR spektroskopijom, a strukture svih novosintetiziranih spojeva potvrđene su 1H NMR i 13C NMR spektroskopijom.

Abstract (english)

The topic of this work was the synthesis of novel amidino-substituted benzothiazole derivatives 8-10 and 16. For the synthesis of target compounds classical methods of organic synthesis were used. The synthesis was carried out by two different starting compounds: 4-chloroaniline and 4-aminobenzonitrile. Synthesis of amidino derivatives 8-10 was performed in five synthetic steps, closing, opening of benzothiazole ring, nucleophilic substitution of bromacetonitrile and Pinner reaction which obtained the target compounds 2-(4-(5-chlorobenzothiazol-2-yl)phenoxy)acetimidamide 8 and
2-(4-((1H-imidazol-2-yl)methoxy) phenyl)-5-chlorobenzothiazole 9, while the synthesis of compound 10 was not successful. The synthesis of 6-amidino-substituted benzothiazole was carried out in four synthetic steps which involved substitution of 4-aminobenzonitrile and potassium thiocyanate, conversion of thiocyanate group into thiol group, closing of benzothiazole ring and Pinner reaction which did not afford target compound 16. The progress of Pinner reactions was monitored by IR spectroscopy, and the structures of all newly synthesized compounds were confirmed by 1H NMR and 13C NMR spectroscopy.

• Keywords: benzotiazol; amidini; organska sinteza; Pinnerova reakcija; 1H NMR spektroskopija; 13C NMR spektroskopija; IR spektroskopija
• Keywords (english): benzothiazole; amidines; organic synthesis; Pinner reaction; 1H NMR spectroscopy; 13C NMR spectroscopy; IR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:603995
• Project: Number: IP-2018-01-4682; Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja; Acronym: PurBioCaPa; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Advanced materials and technologies; 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 resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-05-28 16:47:12