{"id":{"repo_id":"abertay","oai_identifier":"oai:rke.abertay.ac.uk:studenttheses/90b18814-909e-42fd-9ff5-60696063c24d"},"canonical_url":"https://search.dev.ndltd.org/etd/abertay/oai:rke.abertay.ac.uk:studenttheses/90b18814-909e-42fd-9ff5-60696063c24d","repository":{"repo_id":"abertay","name":"Abertay University","base_url":"https://rke.abertay.ac.uk/ws/oai"},"display":{"title":"The synthesis and reactions of sulphur analogues of deoxyvasicinone","abstract":"The synthesis of the thiazolo -, thiazin - and thiazepino- quinazolinones (A)-(C) was achieved, by the condensation of anthranilic acid with appropriate sulphur containing lactams, in the presence of phosphoryl chloride. The quinazolinones (A) and (B) were shown to react (at the methylene group alpha to the carbon-nitrogen double bond) with a variety of electrophiles at elevated temperatures. Compound (C) was found to be inert to electrophiles under the same reaction conditions.<br/><br/>The ability of the heterocycles (A)-(C)to react with heterocumulenes, following deprotonation with sodium hydride in DMSO, was demonstrated. Reaction of the anion derived from (B) with alkylating agents, Michael acceptors and activated halopyridines afforded novel substituted derivatives. The oxidation, Pummerer rearrangement and deacetylation of (A)-(C) was accomplished to yield analogues which were similar in structure to the biologically active compound vasicinone. A series of C-ring substituted analogues of (A) were prepared and the sulphoxides derived from these compounds subjected to Pummerer rearrangement.<br/><br/>(A) and (B) were oxidatively ring opened on treatment with excess peracetic acid, whilst under similar reaction conditions (C) gave a sulphone. Investigations in to the reduction of substituted derivatives of (B) led to the novel tetracyclic compound (D).","abstract_html":"The synthesis of the thiazolo -, thiazin - and thiazepino- quinazolinones (A)-(C) was achieved, by the condensation of anthranilic acid with appropriate sulphur containing lactams, in the presence of phosphoryl chloride. The quinazolinones (A) and (B) were shown to react (at the methylene group alpha to the carbon-nitrogen double bond) with a variety of electrophiles at elevated temperatures. Compound (C) was found to be inert to electrophiles under the same reaction conditions.&lt;br/&gt;&lt;br/&gt;The ability of the heterocycles (A)-(C)to react with heterocumulenes, following deprotonation with sodium hydride in DMSO, was demonstrated. Reaction of the anion derived from (B) with alkylating agents, Michael acceptors and activated halopyridines afforded novel substituted derivatives. The oxidation, Pummerer rearrangement and deacetylation of (A)-(C) was accomplished to yield analogues which were similar in structure to the biologically active compound vasicinone. A series of C-ring substituted analogues of (A) were prepared and the sulphoxides derived from these compounds subjected to Pummerer rearrangement.&lt;br/&gt;&lt;br/&gt;(A) and (B) were oxidatively ring opened on treatment with excess peracetic acid, whilst under similar reaction conditions (C) gave a sulphone. Investigations in to the reduction of substituted derivatives of (B) led to the novel tetracyclic compound (D).","abstract_has_math":false,"creators":["Norrie, Robert"],"institution":null,"degree_name":"PhD","degree_level":"Doctoral Thesis","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1989,"date_issued":"1989-1","date_published":"1989-1","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/90b18814-909e-42fd-9ff5-60696063c24d"],"render_values":[{"text":"oai:rke.abertay.ac.uk:studenttheses/90b18814-909e-42fd-9ff5-60696063c24d","href":null,"code":true}]}]},"links":{"outbound_url":"https://rke.abertay.ac.uk/en/studentTheses/90b18814-909e-42fd-9ff5-60696063c24d","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Norrie, Robert"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1989-1"]},{"key":"dc:date.issued","label":"Date","values":["1989-1"]},{"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/90b18814-909e-42fd-9ff5-60696063c24d"]},{"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/90b18814-909e-42fd-9ff5-60696063c24d","https://rke.abertay.ac.uk/en/studentTheses/90b18814-909e-42fd-9ff5-60696063c24d"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://rke.abertay.ac.uk/files/15677927/Norrie_1989_The_synthesis_and_reactioins_of_PhD.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The synthesis of the thiazolo -, thiazin - and thiazepino- quinazolinones (A)-(C) was achieved, by the condensation of anthranilic acid with appropriate sulphur containing lactams, in the presence of phosphoryl chloride. The quinazolinones (A) and (B) were shown to react (at the methylene group alpha to the carbon-nitrogen double bond) with a variety of electrophiles at elevated temperatures. Compound (C) was found to be inert to electrophiles under the same reaction conditions.<br/><br/>The ability of the heterocycles (A)-(C)to react with heterocumulenes, following deprotonation with sodium hydride in DMSO, was demonstrated. Reaction of the anion derived from (B) with alkylating agents, Michael acceptors and activated halopyridines afforded novel substituted derivatives. The oxidation, Pummerer rearrangement and deacetylation of (A)-(C) was accomplished to yield analogues which were similar in structure to the biologically active compound vasicinone. A series of C-ring substituted analogues of (A) were prepared and the sulphoxides derived from these compounds subjected to Pummerer rearrangement.<br/><br/>(A) and (B) were oxidatively ring opened on treatment with excess peracetic acid, whilst under similar reaction conditions (C) gave a sulphone. Investigations in to the reduction of substituted derivatives of (B) led to the novel tetracyclic compound (D)."]},{"key":"dc:title","label":"Title","values":["The synthesis and reactions of sulphur analogues of deoxyvasicinone"]}]}],"canonical_facts":{"dc:creator":["Norrie, Robert"],"dc:date":["1989-1"],"dc:date.issued":["1989-1"],"dc:description.abstract":["The synthesis of the thiazolo -, thiazin - and thiazepino- quinazolinones (A)-(C) was achieved, by the condensation of anthranilic acid with appropriate sulphur containing lactams, in the presence of phosphoryl chloride. The quinazolinones (A) and (B) were shown to react (at the methylene group alpha to the carbon-nitrogen double bond) with a variety of electrophiles at elevated temperatures. Compound (C) was found to be inert to electrophiles under the same reaction conditions.<br/><br/>The ability of the heterocycles (A)-(C)to react with heterocumulenes, following deprotonation with sodium hydride in DMSO, was demonstrated. Reaction of the anion derived from (B) with alkylating agents, Michael acceptors and activated halopyridines afforded novel substituted derivatives. The oxidation, Pummerer rearrangement and deacetylation of (A)-(C) was accomplished to yield analogues which were similar in structure to the biologically active compound vasicinone. A series of C-ring substituted analogues of (A) were prepared and the sulphoxides derived from these compounds subjected to Pummerer rearrangement.<br/><br/>(A) and (B) were oxidatively ring opened on treatment with excess peracetic acid, whilst under similar reaction conditions (C) gave a sulphone. Investigations in to the reduction of substituted derivatives of (B) led to the novel tetracyclic compound (D)."],"dc:identifier":["oai:rke.abertay.ac.uk:studenttheses/90b18814-909e-42fd-9ff5-60696063c24d","https://rke.abertay.ac.uk/en/studentTheses/90b18814-909e-42fd-9ff5-60696063c24d"],"dc:identifier.uri":["https://rke.abertay.ac.uk/files/15677927/Norrie_1989_The_synthesis_and_reactioins_of_PhD.pdf"],"dc:language":["eng"],"dc:publisher.department":["Dundee Institute of Technology"],"dc:relation.isreferencedby":["https://rke.abertay.ac.uk/en/studentTheses/90b18814-909e-42fd-9ff5-60696063c24d"],"dc:title":["The synthesis and reactions of sulphur analogues of deoxyvasicinone"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["Doctoral Thesis"],"dc:type.qualificationname":["PhD"]},"updated_at":"2026-07-24T00:50:16Z"}