{"id":{"repo_id":"abertay","oai_identifier":"oai:rke.abertay.ac.uk:studenttheses/cc5042b3-b728-4302-909b-3a78323015b1"},"canonical_url":"https://search.dev.ndltd.org/etd/abertay/oai:rke.abertay.ac.uk:studenttheses/cc5042b3-b728-4302-909b-3a78323015b1","repository":{"repo_id":"abertay","name":"Abertay University","base_url":"https://rke.abertay.ac.uk/ws/oai"},"display":{"title":"Synthesis and reactions of some pyridines and thienopyridines","abstract":"The overall aim of this research project is to investigate nucleophilic substitution reactions of the thiomethyl group of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]jpyridine. The multistep synthesis of this compound is reviewed and improvements described. The first step is the N-oxidation of ethyl 3- pyridylacetate, so reagents for the preparation of this and other 3-substituted pyridines were investigated and a novel workup procedure for oxidation with <i>m</i>-CPBA (<i>m</i>-chloroperbenzoic acid) is described. The preparation of ethyl 2-chloro-3-pyridylacetate and several polychlorinated pyridine derivatives are reported. Novel ketene dithioacetals were prepared from ethyl 5-chloro-3-pyridylacetate and 5-chloro-3-pyridylacetonitrile and some were converted to highly substituted thiophenes. Novel thieno[2,3-b]pyridines and [3,2-c]pyridines were prepared from ethyl 2-chloro-3-pyridylacetate, ethyl 4-chloro-3-pyridylacetate and their N-oxides. Preparation of the sulphoxide and sulphone of 3-ethyloxycarbonyl-2- methylthiothieno[2,3-b]pyridine was investigated and their relative susceptibility to substitution by some nitrogen nucleophiles examined. The conversion of benzylamine to benzaldehyde by the N-oxide group during the reaction of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine N-oxide with benzylamine was studied in some detail. Attempts were made to develop a synthetic route to the potential agonist of serotonin, 3-(2-aminoethyl)-5-hydroxythieno[2,3-b]pyridine from 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine. Successful removal of the thiomethyl group at C-2 of 3-ethyloxycarbonyl-2-methylthiothieno[2,3- bjpyridine and progress made in development of the side chain at C-3 is reported. This thesis exhibits evidence of clear progress towards the development of a novel synthetic route to potential agonists of serotonin.","abstract_html":"The overall aim of this research project is to investigate nucleophilic substitution reactions of the thiomethyl group of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]jpyridine. The multistep synthesis of this compound is reviewed and improvements described. The first step is the N-oxidation of ethyl 3- pyridylacetate, so reagents for the preparation of this and other 3-substituted pyridines were investigated and a novel workup procedure for oxidation with &lt;i&gt;m&lt;/i&gt;-CPBA (&lt;i&gt;m&lt;/i&gt;-chloroperbenzoic acid) is described. The preparation of ethyl 2-chloro-3-pyridylacetate and several polychlorinated pyridine derivatives are reported. Novel ketene dithioacetals were prepared from ethyl 5-chloro-3-pyridylacetate and 5-chloro-3-pyridylacetonitrile and some were converted to highly substituted thiophenes. Novel thieno[2,3-b]pyridines and [3,2-c]pyridines were prepared from ethyl 2-chloro-3-pyridylacetate, ethyl 4-chloro-3-pyridylacetate and their N-oxides. Preparation of the sulphoxide and sulphone of 3-ethyloxycarbonyl-2- methylthiothieno[2,3-b]pyridine was investigated and their relative susceptibility to substitution by some nitrogen nucleophiles examined. The conversion of benzylamine to benzaldehyde by the N-oxide group during the reaction of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine N-oxide with benzylamine was studied in some detail. Attempts were made to develop a synthetic route to the potential agonist of serotonin, 3-(2-aminoethyl)-5-hydroxythieno[2,3-b]pyridine from 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine. Successful removal of the thiomethyl group at C-2 of 3-ethyloxycarbonyl-2-methylthiothieno[2,3- bjpyridine and progress made in development of the side chain at C-3 is reported. This thesis exhibits evidence of clear progress towards the development of a novel synthetic route to potential agonists of serotonin.","abstract_has_math":false,"creators":["Sturrock, Keith"],"institution":"University of Abertay Dundee","degree_name":"PhD","degree_level":"Doctoral Thesis","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Bremner, David"],"committee_chairs":[],"committee_members":[],"year":2005,"date_issued":"2005-8","date_published":"2005-8","updated_at":"2026-07-24T00:50:16Z","subjects":[],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["oai:rke.abertay.ac.uk:studenttheses/cc5042b3-b728-4302-909b-3a78323015b1"],"render_values":[{"text":"oai:rke.abertay.ac.uk:studenttheses/cc5042b3-b728-4302-909b-3a78323015b1","href":null,"code":true}]}]},"links":{"outbound_url":"https://rke.abertay.ac.uk/en/studentTheses/cc5042b3-b728-4302-909b-3a78323015b1","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Bremner, David"]},{"key":"dc:creator","label":"Author","values":["Sturrock, Keith"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2005-8"]},{"key":"dc:date.issued","label":"Date","values":["2005-8"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["SET"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Abertay Dundee"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://rke.abertay.ac.uk/en/studentTheses/cc5042b3-b728-4302-909b-3a78323015b1"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Doctoral Thesis"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["PhD"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["oai:rke.abertay.ac.uk:studenttheses/cc5042b3-b728-4302-909b-3a78323015b1","https://rke.abertay.ac.uk/en/studentTheses/cc5042b3-b728-4302-909b-3a78323015b1"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://rke.abertay.ac.uk/files/15438206/Sturrock_2005_Synthesis_and_reactions_of_some_Redacted.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The overall aim of this research project is to investigate nucleophilic substitution reactions of the thiomethyl group of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]jpyridine. The multistep synthesis of this compound is reviewed and improvements described. The first step is the N-oxidation of ethyl 3- pyridylacetate, so reagents for the preparation of this and other 3-substituted pyridines were investigated and a novel workup procedure for oxidation with <i>m</i>-CPBA (<i>m</i>-chloroperbenzoic acid) is described. The preparation of ethyl 2-chloro-3-pyridylacetate and several polychlorinated pyridine derivatives are reported. Novel ketene dithioacetals were prepared from ethyl 5-chloro-3-pyridylacetate and 5-chloro-3-pyridylacetonitrile and some were converted to highly substituted thiophenes. Novel thieno[2,3-b]pyridines and [3,2-c]pyridines were prepared from ethyl 2-chloro-3-pyridylacetate, ethyl 4-chloro-3-pyridylacetate and their N-oxides. Preparation of the sulphoxide and sulphone of 3-ethyloxycarbonyl-2- methylthiothieno[2,3-b]pyridine was investigated and their relative susceptibility to substitution by some nitrogen nucleophiles examined. The conversion of benzylamine to benzaldehyde by the N-oxide group during the reaction of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine N-oxide with benzylamine was studied in some detail. Attempts were made to develop a synthetic route to the potential agonist of serotonin, 3-(2-aminoethyl)-5-hydroxythieno[2,3-b]pyridine from 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine. Successful removal of the thiomethyl group at C-2 of 3-ethyloxycarbonyl-2-methylthiothieno[2,3- bjpyridine and progress made in development of the side chain at C-3 is reported. This thesis exhibits evidence of clear progress towards the development of a novel synthetic route to potential agonists of serotonin."]},{"key":"dc:title","label":"Title","values":["Synthesis and reactions of some pyridines and thienopyridines"]}]}],"canonical_facts":{"dc:contributor.advisor":["Bremner, David"],"dc:creator":["Sturrock, Keith"],"dc:date":["2005-8"],"dc:date.issued":["2005-8"],"dc:description.abstract":["The overall aim of this research project is to investigate nucleophilic substitution reactions of the thiomethyl group of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]jpyridine. The multistep synthesis of this compound is reviewed and improvements described. The first step is the N-oxidation of ethyl 3- pyridylacetate, so reagents for the preparation of this and other 3-substituted pyridines were investigated and a novel workup procedure for oxidation with <i>m</i>-CPBA (<i>m</i>-chloroperbenzoic acid) is described. The preparation of ethyl 2-chloro-3-pyridylacetate and several polychlorinated pyridine derivatives are reported. Novel ketene dithioacetals were prepared from ethyl 5-chloro-3-pyridylacetate and 5-chloro-3-pyridylacetonitrile and some were converted to highly substituted thiophenes. Novel thieno[2,3-b]pyridines and [3,2-c]pyridines were prepared from ethyl 2-chloro-3-pyridylacetate, ethyl 4-chloro-3-pyridylacetate and their N-oxides. Preparation of the sulphoxide and sulphone of 3-ethyloxycarbonyl-2- methylthiothieno[2,3-b]pyridine was investigated and their relative susceptibility to substitution by some nitrogen nucleophiles examined. The conversion of benzylamine to benzaldehyde by the N-oxide group during the reaction of 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine N-oxide with benzylamine was studied in some detail. Attempts were made to develop a synthetic route to the potential agonist of serotonin, 3-(2-aminoethyl)-5-hydroxythieno[2,3-b]pyridine from 3-ethyloxycarbonyl-2-methylthiothieno[2,3-b]pyridine. Successful removal of the thiomethyl group at C-2 of 3-ethyloxycarbonyl-2-methylthiothieno[2,3- bjpyridine and progress made in development of the side chain at C-3 is reported. This thesis exhibits evidence of clear progress towards the development of a novel synthetic route to potential agonists of serotonin."],"dc:identifier":["oai:rke.abertay.ac.uk:studenttheses/cc5042b3-b728-4302-909b-3a78323015b1","https://rke.abertay.ac.uk/en/studentTheses/cc5042b3-b728-4302-909b-3a78323015b1"],"dc:identifier.uri":["https://rke.abertay.ac.uk/files/15438206/Sturrock_2005_Synthesis_and_reactions_of_some_Redacted.pdf"],"dc:language":["eng"],"dc:publisher.department":["SET"],"dc:publisher.institution":["University of Abertay Dundee"],"dc:relation.isreferencedby":["https://rke.abertay.ac.uk/en/studentTheses/cc5042b3-b728-4302-909b-3a78323015b1"],"dc:title":["Synthesis and reactions of some pyridines and thienopyridines"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["Doctoral Thesis"],"dc:type.qualificationname":["PhD"]},"updated_at":"2026-07-24T00:50:16Z"}