Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles

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 imidatsolijohdanna...

Full description

Bibliographic Details
Main Author: Peltonen, Risto
Other Authors: Matemaattis-luonnontieteellinen tiedekunta, Faculty of Sciences, Kemian laitos, Department of Chemistry, Jyväskylän yliopisto, University of Jyväskylä
Format: Master's thesis
Language:eng
Published: 2023
Subjects:
Online Access: https://jyx.jyu.fi/handle/123456789/86607
_version_ 1826225766403145728
author Peltonen, Risto
author2 Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä
author_facet Peltonen, Risto Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä Peltonen, Risto Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä
author_sort Peltonen, Risto
datasource_str_mv jyx
description 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.
first_indexed 2024-09-11T08:49:01Z
format Pro gradu
free_online_boolean 1
fullrecord [{"key": "dc.contributor.advisor", "value": "Valkonen, Arto", "language": "", "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.author", "value": "Peltonen, Risto", "language": "", "element": "contributor", "qualifier": "author", "schema": "dc"}, {"key": "dc.date.accessioned", "value": "2023-04-26T07:18:11Z", "language": null, "element": "date", "qualifier": "accessioned", "schema": "dc"}, {"key": "dc.date.available", "value": "2023-04-26T07:18:11Z", "language": null, "element": "date", "qualifier": "available", "schema": "dc"}, {"key": "dc.date.issued", "value": "2023", "language": "", "element": "date", "qualifier": "issued", "schema": "dc"}, {"key": "dc.identifier.uri", "value": "https://jyx.jyu.fi/handle/123456789/86607", "language": null, "element": "identifier", "qualifier": "uri", "schema": "dc"}, {"key": "dc.description.abstract", "value": "Ty\u00f6n kirjallisuuskatsauksessa tutkittiin N,N\u2019-substituoitujen imidatsoli-2-tionien synteesi\u00e4 ja\nniihin liittyv\u00e4\u00e4 teoriaa. N,N\u2019-Substituoituja imidatsoli-2-tioneita voidaan syntetisoida k\u00e4ytt\u00e4m\u00e4ll\u00e4\nmonia eri l\u00e4ht\u00f6aineita ja katalyyttej\u00e4. Lopputuloksena on iso skaala tuotteita. N\u00e4m\u00e4\nimidatsolijohdannaiset ovat bioaktiivisia, aivan kuten muutkin atsolit. T\u00e4st\u00e4 syyst\u00e4 imidatsoli-2-\ntionien k\u00e4yt\u00e4nn\u00f6n sovellutukset ovat bio-, maanviljely- ja l\u00e4\u00e4kekemian parissa. My\u00f6s\nkoordinaatiokemiasta l\u00f6ytyy sovellutuksia imidatsoli-2-tioneille.\nK\u00e4yt\u00e4nn\u00f6n osuudessa syntetisoitiin N,N\u2019-substituoituja imidatsoli-2-tioneita erilaisista\nbromimetyylibentseeneist\u00e4 ja imidatsolijohdannaisista. Kyseisess\u00e4 reaktiossa hy\u00f6dynnett\u00e4vi\u00e4\nimidatsolijohdannaisia tunnetaan paljon. Kaikki tehdyt reaktiot tuottivat raakatuotetta hyv\u00e4ll\u00e4\nsaannolla, mutta monet tuotteista olivat puhdistusta kaipaavia seoksia. Osa tuotteista ei\npuhdistunut yrityksist\u00e4 huolimatta tai ne menetettiin puhdistusprosessissa. Tuotteista mitattiin 1H-\n, 13C-, 1H, 13C HMBC- ja 1H, 15N korrelaatio NMR ja ESI-MS spektrit. My\u00f6s sulamispiste\nmitattiin puhtaista tuotteista. Kymmenen kiderakennetta saatiin m\u00e4\u00e4ritetty\u00e4 syntetisoiduista\ntuotteista ja nelj\u00e4 niiden komplekseista halogeenisidosdonorien kanssa\nyksikider\u00f6ntgendiffraktiomenetelm\u00e4ll\u00e4.", "language": "fi", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.abstract", "value": "The literature review of this thesis was done by reviewing articles considering synthesis of N,N\u2019-\nsubstituted imidazole-2-thiones and theory regarding them. N,N\u2019-Substituted imidazole-2-thiones\ncan be synthesized with many different starting materials and catalysts, resulting in various\ndifferent sized molecules. As all azoles, these imidazole derivates are bioactive. This is the reason\nwhy 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\nchemistry as well.\nThe experimental section of this thesis is about synthesizing N,N\u2019-substituted imidazole-2-thiones\nfrom different bromomethylbenzenes and imidazole derivatives. Many imidazole derivatives are\nknown, and they can be used as reagent in this synthesis. All the experiments made worked out to\nsome degree, giving raw product in good yields. Products were dirty or mixtures and needed\npurification. Purification made yields drop and some products could not be purified or were lost\nduring purification. Standard 1H-,\n13C-,\n1H, 13C HMBC- and 1H, 15N correlation NMR and ESIMS spectra were measured from every purified sample and some of the raw products. Also melting\npoints of the pure products were measured. Ten crystal structures from the synthetic products and\nfour of their complexes with halogen bonding donors were determined with single crystal X-ray\ndiffraction method.", "language": "en", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Submitted by Paivi Vuorio (paelvuor@jyu.fi) on 2023-04-26T07:18:11Z\nNo. of bitstreams: 0", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Made available in DSpace on 2023-04-26T07:18:11Z (GMT). No. of bitstreams: 0\n Previous issue date: 2023", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.format.extent", "value": "126", "language": "", "element": "format", "qualifier": "extent", "schema": "dc"}, {"key": "dc.language.iso", "value": "eng", "language": null, "element": "language", "qualifier": "iso", "schema": "dc"}, {"key": "dc.rights", "value": "In Copyright", "language": null, "element": "rights", "qualifier": null, "schema": "dc"}, {"key": "dc.title", "value": "Synthesis of N,N\u2019-substituted imidazole-2-thiones from N-substituted imidazoles", "language": "", "element": "title", "qualifier": null, "schema": "dc"}, {"key": "dc.type", "value": "master thesis", "language": null, "element": "type", "qualifier": null, "schema": "dc"}, {"key": "dc.identifier.urn", "value": "URN:NBN:fi:jyu-202304262714", "language": "", "element": "identifier", "qualifier": "urn", "schema": "dc"}, {"key": "dc.type.ontasot", "value": "Master\u2019s thesis", "language": "en", "element": "type", "qualifier": "ontasot", "schema": "dc"}, {"key": "dc.type.ontasot", "value": "Pro gradu -tutkielma", "language": "fi", "element": "type", "qualifier": "ontasot", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Matemaattis-luonnontieteellinen tiedekunta", "language": "fi", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Faculty of Sciences", "language": "en", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Kemian laitos", "language": "fi", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Department of Chemistry", "language": "en", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "Jyv\u00e4skyl\u00e4n yliopisto", "language": "fi", "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "University of Jyv\u00e4skyl\u00e4", "language": "en", "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.subject.discipline", "value": "Orgaaninen kemia", "language": "fi", "element": "subject", "qualifier": "discipline", "schema": "dc"}, {"key": "dc.subject.discipline", "value": "Organic Chemistry", "language": "en", "element": "subject", "qualifier": "discipline", "schema": "dc"}, {"key": "yvv.contractresearch.funding", "value": "0", "language": "", "element": "contractresearch", "qualifier": "funding", "schema": "yvv"}, {"key": "dc.type.coar", "value": "http://purl.org/coar/resource_type/c_bdcc", "language": null, "element": "type", "qualifier": "coar", "schema": "dc"}, {"key": "dc.rights.copyright", "value": "\u00a9 The Author(s)", "language": null, "element": "rights", "qualifier": "copyright", "schema": "dc"}, {"key": "dc.rights.accesslevel", "value": "openAccess", "language": null, "element": "rights", "qualifier": "accesslevel", "schema": "dc"}, {"key": "dc.type.publication", "value": "masterThesis", "language": null, "element": "type", "qualifier": "publication", "schema": "dc"}, {"key": "dc.subject.oppiainekoodi", "value": "4035", "language": "", "element": "subject", "qualifier": "oppiainekoodi", "schema": "dc"}, {"key": "dc.subject.yso", "value": "orgaaninen kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "atsolit", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "synteesi", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "reaktiot", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "organic chemistry", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "chemistry", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "azoles", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "synthesis", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "reactions", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.rights.url", "value": "https://rightsstatements.org/page/InC/1.0/", "language": null, "element": "rights", "qualifier": "url", "schema": "dc"}]
id jyx.123456789_86607
language eng
last_indexed 2025-02-18T10:56:13Z
main_date 2023-01-01T00:00:00Z
main_date_str 2023
online_boolean 1
online_urls_str_mv {"url":"https:\/\/jyx.jyu.fi\/bitstreams\/2b154ea6-b03e-4ac4-a8c8-e85c5e3f6022\/download","text":"URN:NBN:fi:jyu-202304262714.pdf","source":"jyx","mediaType":"application\/pdf"}
publishDate 2023
record_format qdc
source_str_mv jyx
spellingShingle Peltonen, Risto Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles Orgaaninen kemia Organic Chemistry 4035 orgaaninen kemia kemia atsolit synteesi reaktiot organic chemistry chemistry azoles synthesis reactions
title Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
title_full Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
title_fullStr Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
title_full_unstemmed Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
title_short Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
title_sort synthesis of n n substituted imidazole 2 thiones from n substituted imidazoles
title_txtP Synthesis of N,N’-substituted imidazole-2-thiones from N-substituted imidazoles
topic Orgaaninen kemia Organic Chemistry 4035 orgaaninen kemia kemia atsolit synteesi reaktiot organic chemistry chemistry azoles synthesis reactions
topic_facet 4035 Orgaaninen kemia Organic Chemistry atsolit azoles chemistry kemia orgaaninen kemia organic chemistry reactions reaktiot synteesi synthesis
url https://jyx.jyu.fi/handle/123456789/86607 http://www.urn.fi/URN:NBN:fi:jyu-202304262714
work_keys_str_mv AT peltonenristo synthesisofnnsubstitutedimidazole2thionesfromnsubstitutedimidazoles