{"id":{"repo_id":"abertay","oai_identifier":"oai:rke.abertay.ac.uk:studenttheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6"},"canonical_url":"https://search.dev.ndltd.org/etd/abertay/oai:rke.abertay.ac.uk:studenttheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6","repository":{"repo_id":"abertay","name":"Abertay University","base_url":"https://rke.abertay.ac.uk/ws/oai"},"display":{"title":"The synthesis and reactions of thienopyridines","abstract":"The synthesis of ortho-halogenated pyridine derivatives (A-D; R = CN, CO2Et; R1 = CN, CO2Me, CO2Et) containing methylene groups activated by the nitrile or ester functionality is described. Derivatives (A-D) are reacted with carbon disulfide in the presence of base, followed by alkylation with iodomethane, to afford novel thienopyridines (E-H; R = CN, CO2Et; R1 = CN, CO2Me, CO2Et; X = SMe).
Pyridine derivative (B; R = CN) also reacts with phenyl isothiocyanate to form thienopyridine (F; R = CN; X = NHPh). Reaction of the nitriles (A, C and D; R, R1 = CN) under identical conditions, however, does not give the bicyclic compounds but ketene dithioacetals (I, J and K). Increasing the reaction temperature allows formation of thienopyridines (E, G and H; R, R1 = CN; X = NHPh). Thienopyridines R = CO2Et; R1 = CO2Me, CO2Et; X = NHPh) are also synthesised from the ruction of the derivatives (A-D; R = CO2Et; = CO2Me; CO2Et) with phenyl isothiocyanate.
Reaction of nitrile (A; R1 = CN) with carbon disulfide in the presence of base, followed by quenching with ethyl chloroacetate affords thienopyridine (E; R1 = CN; X = SCH2CO2Et) which in turn cyclises with base to give tricyclic compound (L).
Thienopyridines (E; R1 = NH2; X = CN, Ph, CO2Et, COMe, COPh, COCH2CO2Et) are synthesised from reactions of 3-cyanopyridine-2(lH)-thione with compounds containing a halogen atom adjacent to an active methylene group.
Nucleophilic reactions of thienopyridines (E; R1 = CN; X = SMe, SOMe, SO2Me) are investigated, in an attempt to prepare tricyclic compounds.","abstract_html":"The synthesis of <i>ortho</i>-halogenated pyridine derivatives (A-D; R = CN, CO<sub>2</sub>Et; R<sub>1</sub> = CN, CO<sub>2</sub>Me, CO<sub>2</sub>Et) containing methylene groups activated by the nitrile or ester functionality is described. Derivatives (A-D) are reacted with carbon disulfide in the presence of base, followed by alkylation with iodomethane, to afford novel thienopyridines (E-H; R = CN, CO<sub>2</sub>Et; R<sub>1</sub> = CN, CO<sub>2</sub>Me, CO<sub>2</sub>Et; X = SMe).<br/><br/>Pyridine derivative (B; R = CN) also reacts with phenyl isothiocyanate to form thienopyridine (F; R = CN; X = NHPh). Reaction of the nitriles (A, C and D; R, R<sub>1</sub> = CN) under identical conditions, however, does not give the bicyclic compounds but ketene dithioacetals (I, J and K). Increasing the reaction temperature allows formation of thienopyridines (E, G and H; R, R<sub>1</sub> = CN; X = NHPh). Thienopyridines R = CO<sub>2</sub>Et; R<sub>1</sub> = CO<sub>2</sub>Me, CO<sub>2</sub>Et; X = NHPh) are also synthesised from the ruction of the derivatives (A-D; R = CO<sub>2</sub>Et; = CO<sub>2</sub>Me; CO<sub>2</sub>Et) with phenyl isothiocyanate.<br/><br/>Reaction of nitrile (A; R<sub>1</sub> = CN) with carbon disulfide in the presence of base, followed by quenching with ethyl chloroacetate affords thienopyridine (E; R1 = CN; X = SCH<sub>2</sub>CO<sub>2</sub>Et) which in turn cyclises with base to give tricyclic compound (L).<br/><br/>Thienopyridines (E; R<sub>1</sub> = NH<sub>2</sub>; X = CN, Ph, CO<sub>2</sub>Et, COMe, COPh, COCH<sub>2</sub>CO<sub>2</sub>Et) are synthesised from reactions of 3-cyanopyridine-2(lH)-thione with compounds containing a halogen atom adjacent to an active methylene group.<br/><br/>Nucleophilic reactions of thienopyridines (E; R<sub>1</sub> = CN; X = SMe, SOMe, SO<sub>2</sub>Me) are investigated, in an attempt to prepare tricyclic compounds.","abstract_has_math":false,"creators":["Wilson, Kenneth"],"institution":null,"degree_name":"PhD","degree_level":"Doctoral Thesis","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Bremner, David"],"committee_chairs":[],"committee_members":[],"year":1992,"date_issued":"1992-1","date_published":"1992-1","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/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6"],"render_values":[{"text":"oai:rke.abertay.ac.uk:studenttheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6","href":null,"code":true}]}]},"links":{"outbound_url":"https://rke.abertay.ac.uk/en/studentTheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6","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":["Wilson, Kenneth"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1992-1"]},{"key":"dc:date.issued","label":"Date","values":["1992-1"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Dundee Institute of Technology"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://rke.abertay.ac.uk/en/studentTheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6"]},{"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/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6","https://rke.abertay.ac.uk/en/studentTheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://rke.abertay.ac.uk/files/15627185/Wilson_1991_The_synthesis_and_reactions_of_PhD.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The synthesis of ortho-halogenated pyridine derivatives (A-D; R = CN, CO2Et; R1 = CN, CO2Me, CO2Et) containing methylene groups activated by the nitrile or ester functionality is described. Derivatives (A-D) are reacted with carbon disulfide in the presence of base, followed by alkylation with iodomethane, to afford novel thienopyridines (E-H; R = CN, CO2Et; R1 = CN, CO2Me, CO2Et; X = SMe).
Pyridine derivative (B; R = CN) also reacts with phenyl isothiocyanate to form thienopyridine (F; R = CN; X = NHPh). Reaction of the nitriles (A, C and D; R, R1 = CN) under identical conditions, however, does not give the bicyclic compounds but ketene dithioacetals (I, J and K). Increasing the reaction temperature allows formation of thienopyridines (E, G and H; R, R1 = CN; X = NHPh). Thienopyridines R = CO2Et; R1 = CO2Me, CO2Et; X = NHPh) are also synthesised from the ruction of the derivatives (A-D; R = CO2Et; = CO2Me; CO2Et) with phenyl isothiocyanate.
Reaction of nitrile (A; R1 = CN) with carbon disulfide in the presence of base, followed by quenching with ethyl chloroacetate affords thienopyridine (E; R1 = CN; X = SCH2CO2Et) which in turn cyclises with base to give tricyclic compound (L).
Thienopyridines (E; R1 = NH2; X = CN, Ph, CO2Et, COMe, COPh, COCH2CO2Et) are synthesised from reactions of 3-cyanopyridine-2(lH)-thione with compounds containing a halogen atom adjacent to an active methylene group.
Nucleophilic reactions of thienopyridines (E; R1 = CN; X = SMe, SOMe, SO2Me) are investigated, in an attempt to prepare tricyclic compounds."]},{"key":"dc:title","label":"Title","values":["The synthesis and reactions of thienopyridines"]}]}],"canonical_facts":{"dc:contributor.advisor":["Bremner, David"],"dc:creator":["Wilson, Kenneth"],"dc:date":["1992-1"],"dc:date.issued":["1992-1"],"dc:description.abstract":["The synthesis of ortho-halogenated pyridine derivatives (A-D; R = CN, CO2Et; R1 = CN, CO2Me, CO2Et) containing methylene groups activated by the nitrile or ester functionality is described. Derivatives (A-D) are reacted with carbon disulfide in the presence of base, followed by alkylation with iodomethane, to afford novel thienopyridines (E-H; R = CN, CO2Et; R1 = CN, CO2Me, CO2Et; X = SMe).
Pyridine derivative (B; R = CN) also reacts with phenyl isothiocyanate to form thienopyridine (F; R = CN; X = NHPh). Reaction of the nitriles (A, C and D; R, R1 = CN) under identical conditions, however, does not give the bicyclic compounds but ketene dithioacetals (I, J and K). Increasing the reaction temperature allows formation of thienopyridines (E, G and H; R, R1 = CN; X = NHPh). Thienopyridines R = CO2Et; R1 = CO2Me, CO2Et; X = NHPh) are also synthesised from the ruction of the derivatives (A-D; R = CO2Et; = CO2Me; CO2Et) with phenyl isothiocyanate.
Reaction of nitrile (A; R1 = CN) with carbon disulfide in the presence of base, followed by quenching with ethyl chloroacetate affords thienopyridine (E; R1 = CN; X = SCH2CO2Et) which in turn cyclises with base to give tricyclic compound (L).
Thienopyridines (E; R1 = NH2; X = CN, Ph, CO2Et, COMe, COPh, COCH2CO2Et) are synthesised from reactions of 3-cyanopyridine-2(lH)-thione with compounds containing a halogen atom adjacent to an active methylene group.
Nucleophilic reactions of thienopyridines (E; R1 = CN; X = SMe, SOMe, SO2Me) are investigated, in an attempt to prepare tricyclic compounds."],"dc:identifier":["oai:rke.abertay.ac.uk:studenttheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6","https://rke.abertay.ac.uk/en/studentTheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6"],"dc:identifier.uri":["https://rke.abertay.ac.uk/files/15627185/Wilson_1991_The_synthesis_and_reactions_of_PhD.pdf"],"dc:language":["eng"],"dc:publisher.department":["Dundee Institute of Technology"],"dc:relation.isreferencedby":["https://rke.abertay.ac.uk/en/studentTheses/a399e9f6-e2c3-4dc4-81a8-85aa2e0614e6"],"dc:title":["The synthesis and reactions of thienopyridines"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["Doctoral Thesis"],"dc:type.qualificationname":["PhD"]},"updated_at":"2026-07-24T00:50:16Z"}