1,2,3-triazolni derivati benztiazola: sinteza i strukturna karakterizacija

undergraduate thesis

• Title (english): 1,2,3-triazole derivatives of benzothiazole: synthesis and structural characterization
• Author: Ivona Čipor
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Committee member: Nataša Perin (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-18, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U ovom radu opisana je sinteza novih benztiazolnih derivata supstituiranih 1,2,3-triazolnim prstenom. Pristupom molekulske hibridizacije povezane su alifatske i aromatske strukturne komponente s benztiazolnom jezgrom premoštene 1,2,3-triazolnom poveznicom. Reakcijom 2-supstituiranih 6-aminobenztiazola s tert-butilnitritom i trimetilsilil-azidom u acetonitrilu pripravljeni su 6-azido derivati benztiazola 1-5, koji su nadalje mikrovalovima potpomognutom klik-reakcijom kataliziranom bakrom s terminalnim alkinima prevedeni u 1,2,3-triazolne derivate benztiazola 6, 7 i 9. Strukture svih sintetiziranih spojeva potvrđene su 1H-NMR spektroskopijom. Derivati benztiazola 1, 2 i 7 su spektroskopski okarakterizirani UV/Vis spektroskopijom, te su im određeni maksimumi apsorbancije i valne duljine emisije.

Abstract (english)

This paper describes the synthesis of novel benzothiazole derivatives substituted with a 1,2,3-triazole ring. Aliphatic and aromatic structural components are linked to the benzothiazole core through 1,2,3-triazole linker by molecular hybridization approach. 6-azido derivatives of benzothiazole 1-5 were synthethized by a reaction of 2-substituted 6-aminobenzothiazoles with tert-butylnitrite and trimethylsilyl-azide in acetonitrile. The 6-azido derivatives were then transformed to novel 1,2,3-triazole derivatives 6, 7 and 9 using terminal alkynes by the microwave supported click reaction catalyzed with copper. Structures of all synthetized compounds were confirmed with 1H-NMR spectroscopy. Derivatives of benzothiazole 1, 2 and 7 were spectroscopically characterized by UV/Vis spectroscopy and their maximums of absorbance and wavelengths of emmision were determined.

• Keywords: benztiazol; 1 2 3-triazol; klik kemija; molekulska hibridizacija
• Keywords (english): benzothiazole; 1 2 3-triazole; click chemistry; molecular hybridization approach
• Language: croatian
• URN:NBN: urn:nbn:hr:149:304775
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2022-05-17 11:41:57