Sinteza, optimiranje reakcijskih uvjeta i strukturna karakterizacija novih akrilonitrilnih derivata benzoksazola priređenih metodama zelene kemije

master's thesis

• Title (english): Synthesis, optimization of reaction conditions and structural characterization of novel acrylonitrile derived benzoxazoles prepared by green chemistry methods
• Author: Tamara Rohtek
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Vesna Ocelić Bulatović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-07-11, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Derivati 2-cijanometilbenzoksazola i akrilonitrilni derivati benzoksazola važna su skupina heterocikličkih spojeva koji pokazuju široki spektar biološkog djelovanja. U ovom radu opisana je sinteza i strukturna karakterizacija 2-cijanometilnih i akrilonitrilnih derivata benzoksazola. Ciljani spojeva priređeni su klasičnim reakcijama organske sinteze i sinteze potpomognute mikrovalnim zračenjem. U prvom koraku sinteze, nukleofilnim napadom malononitrila 1 priređen je etil-2-cijanoacetamidat-hidroklorid 2. Konvencionalnim i zelenim metodama ciklizacije iz spoja 2 i odgovarajućih različito supstituiranih aminofenola 3, 6 i 8 priređeni su glavni prekursori, 2-cijanometilbenzoksazoli 4, 7 i 9. Reakcijom Knoevenagelove kondenzacije iz glavnih prekursora 4, 7 i 9 te odgovarajućih aromatskih aldehida 10-15 i 34-41 priređeni su akrilonitrilni derivati benzoksazola 16-27, 42, 43 i 46-49. Akrilonitrilni derivati benzoksazola 28-30, 44 i 45 nisu uspješno priređeni korištenom metodom te je metodu potrebno dodatno optimirati. Spojevi 31-33 dobiveni su kao smjese E- i Z-izomera. Strukture novopriređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom, kao i
MS spektrometrijom.

Abstract (english)

2-cyanomethylbenzoxazole derivatives and acrylonitrile derived benzoxazoles are an important group of heterocyclic compounds since they exhibit a broad spectrum of biological activities. This work describes the synthesis and structural characterization of 2-cyanomethyl and novel acrylonitrile derived benzoxazoles. The target compounds were prepared by using the standard reactions of organic synthesis and microwave-assisted synthesis. In the first step of the synthesis, ethyl-2-cyanoacetamidate hydrochloride 2 was prepared by nucleophilic reaction of malononitrile 1. The main precursors, 2-cyanomethylbenzoxazoles 4, 7 i 9 were prepared conventional and green synthetic methods, from compounds 3, 6 and 8 in the reaction cyclization with compounds 2. Acrylonitrile derived benzoxazoles 16-27, 42, 43 and 46-49 were prepared in the Knoevenagel condensation from the main precursors 4, 7 and 9 and the corresponding aromatic aldehydes 10-15 and 34-41. Acrylonitriles 28-30, 44 and 45 were not successfully prepared and the method should be further optimized. Compound 31-33 were found to exist as a mixture of E- and Z-isomers. The structures of the newly prepared compounds were confirmed by 1H and 13C NMR spectroscopy as well as by MS spectrometry.

• Keywords: benzoksazoli; 2-cijanometilbenzoksazoli; akrilonitrili; MW potpomognuta sinteza; zelena sinteza; 1H i 13C NMR spektroskopija; MS spektrometrija
• Keywords (english): benzoxazoles; 2-cyanomethylbenzoxazoles; acrylonitriles; microwave-assisted synthesis; green synthesis; 1H and 13C NMR spectroscopy; MS spectrometry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:496104
• Study programme: Title: Materials Science and Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: sveučilišni/a magistar/magistra inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-07-01
• Created on: 2024-07-15 13:04:15