Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
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2023Copyright
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Työn kirjallisuuskatsauksessa tutkittiin N,N’-substituoitujen imidatsoli-2-tionien synteesiä ja
niihin liittyvää teoriaa. N,N’-Substituoituja imidatsoli-2-tioneita voidaan syntetisoida käyttämällä
monia eri lähtöaineita ja katalyyttejä. Lopputuloksena on iso skaala tuotteita. Nämä
imidatsolijohdannaiset ovat bioaktiivisia, aivan kuten muutkin atsolit. Tästä syystä imidatsoli-2-
tionien käytännön sovellutukset ovat bio-, maanviljely- ja lääkekemian parissa. Myös
koordinaatiokemiasta löytyy sovellutuksia imidatsoli-2-tioneille.
Käytännön osuudessa syntetisoitiin N,N’-substituoituja imidatsoli-2-tioneita erilaisista
bromimetyylibentseeneistä ja imidatsolijohdannaisista. Kyseisessä reaktiossa hyödynnettäviä
imidatsolijohdannaisia tunnetaan paljon. Kaikki tehdyt reaktiot tuottivat raakatuotetta hyvällä
saannolla, mutta monet tuotteista olivat puhdistusta kaipaavia seoksia. Osa tuotteista ei
puhdistunut yrityksistä huolimatta tai ne menetettiin puhdistusprosessissa. Tuotteista mitattiin 1H-
, 13C-, 1H, 13C HMBC- ja 1H, 15N korrelaatio NMR ja ESI-MS spektrit. Myös sulamispiste
mitattiin puhtaista tuotteista. Kymmenen kiderakennetta saatiin määritettyä syntetisoiduista
tuotteista ja neljä niiden komplekseista halogeenisidosdonorien kanssa
yksikideröntgendiffraktiomenetelmällä.
...
The literature review of this thesis was done by reviewing articles considering synthesis of N,N’-
substituted imidazole-2-thiones and theory regarding them. N,N’-Substituted imidazole-2-thiones
can be synthesized with many different starting materials and catalysts, resulting in various
different sized molecules. As all azoles, these imidazole derivates are bioactive. This is the reason
why many of the practical applications of imidazole-2-thiones are in the fields of bio-, agriculturaland pharmaceutical chemistry, although there are some other applications in coordination
chemistry as well.
The experimental section of this thesis is about synthesizing N,N’-substituted imidazole-2-thiones
from different bromomethylbenzenes and imidazole derivatives. Many imidazole derivatives are
known, and they can be used as reagent in this synthesis. All the experiments made worked out to
some degree, giving raw product in good yields. Products were dirty or mixtures and needed
purification. Purification made yields drop and some products could not be purified or were lost
during purification. Standard 1H-,
13C-,
1H, 13C HMBC- and 1H, 15N correlation NMR and ESIMS spectra were measured from every purified sample and some of the raw products. Also melting
points of the pure products were measured. Ten crystal structures from the synthetic products and
four of their complexes with halogen bonding donors were determined with single crystal X-ray
diffraction method.
...
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