{"id":{"repo_id":"aston","oai_identifier":"oai:publications.aston.ac.uk:10694"},"canonical_url":"https://search.dev.ndltd.org/etd/aston/oai:publications.aston.ac.uk:10694","repository":{"repo_id":"aston","name":"Aston University","base_url":"https://publications.aston.ac.uk/cgi/oai2"},"display":{"title":"Pyrrolo [2-3-b] Pyridines of Potential Chemotherapeutic Value","abstract":"The methods available for the synthesis of pyrrolopyridines and the biological activity of the pyrrolo [2,3-b] pyridines are reviewed briefly. The reasons for the synthesis of pyrrolo [2. 3- b] pyridines from a pyrrole precursor are discussed and the possible routes from the available starting materials outlined. The synthesis of pyrrolo [2, 3-b] pyridines was approached by two main routes. The attempted syntheses of pyrroto|2,3-b] pyridines from 3-substitued 2-aminopyrroles are discussed and a possible explanation of the failure of these reactions is postulated. The preparation of a series of 2-amino-4-cyanopyrroles and their reaction with 1,3-dicarbonyl reagents to give pyrrolo [2. 3- b] pyridines: is discussed. The two-stage synthesis of pyrrolo[ 2, 3- b] pyridin-4 (7H)- ones from 2-amino-4-cyanopyrroles and diethyl ethoxymethylenemalonate is discussed. The preferred orientation of products obtained from the reaction between 2-amino-4-cyanopyrroles and unsymmetrical dicarbonyl reagents is discussed in terms of a reaction mechanism, The chemistry of the pyrrolo [2,3-3] pyridines is discussed. 13C nuclear magnetic resonance spectroscopy 1H-pyrrolo-[2.3-b] pyridine is discussed and the chemical shifts are rationalised in terms of electron density calculations. The 13C chemical shifts of 1H-pyrrolo[3,2-b] pyridine and 1H-pyrrolo [3,2-c] pyridine are compared with those of 1H-pyrrolo-[2:3-b] pyriaine. The 13C chemical shifts of a series of pyrrolo[2,3-b] pyridine derivatives are recorded, and a comparison of the chemical shift data with available data for methyl-substituted pyridines was made. The comparison of data established the product of the reaction between an aminopyrrole and 4,4-dimethoxybutan-2-one to be a 6-methylpyrrolo |2,3-b| pyridine and not a 4-methylpyrrolo [ 2,3~b] pyridine. The mass spectra of most of the compounds prepared in this work are recorded and possible fragmentation pathways are postulated.","abstract_html":"The methods available for the synthesis of pyrrolopyridines and the biological activity of the pyrrolo [2,3-b] pyridines are reviewed briefly. The reasons for the synthesis of pyrrolo [2. 3- b] pyridines from a pyrrole precursor are discussed and the possible routes from the available starting materials outlined. The synthesis of pyrrolo [2, 3-b] pyridines was approached by two main routes. The attempted syntheses of pyrroto|2,3-b] pyridines from 3-substitued 2-aminopyrroles are discussed and a possible explanation of the failure of these reactions is postulated. The preparation of a series of 2-amino-4-cyanopyrroles and their reaction with 1,3-dicarbonyl reagents to give pyrrolo [2. 3- b] pyridines: is discussed. The two-stage synthesis of pyrrolo[ 2, 3- b] pyridin-4 (7H)- ones from 2-amino-4-cyanopyrroles and diethyl ethoxymethylenemalonate is discussed. The preferred orientation of products obtained from the reaction between 2-amino-4-cyanopyrroles and unsymmetrical dicarbonyl reagents is discussed in terms of a reaction mechanism, The chemistry of the pyrrolo [2,3-3] pyridines is discussed. 13C nuclear magnetic resonance spectroscopy 1H-pyrrolo-[2.3-b] pyridine is discussed and the chemical shifts are rationalised in terms of electron density calculations. The 13C chemical shifts of 1H-pyrrolo[3,2-b] pyridine and 1H-pyrrolo [3,2-c] pyridine are compared with those of 1H-pyrrolo-[2:3-b] pyriaine. The 13C chemical shifts of a series of pyrrolo[2,3-b] pyridine derivatives are recorded, and a comparison of the chemical shift data with available data for methyl-substituted pyridines was made. The comparison of data established the product of the reaction between an aminopyrrole and 4,4-dimethoxybutan-2-one to be a 6-methylpyrrolo |2,3-b| pyridine and not a 4-methylpyrrolo [ 2,3~b] pyridine. The mass spectra of most of the compounds prepared in this work are recorded and possible fragmentation pathways are postulated.","abstract_has_math":false,"creators":["Brodrick, Andrew"],"institution":"Aston University","degree_name":"Ph.D.","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1975,"date_issued":"1975-10","date_published":"1975-10","updated_at":"2026-07-24T01:01:19Z","subjects":[],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":null,"outbound_label":null,"outbound_source":null},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Brodrick, Andrew"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1975-10"]},{"key":"dc:date.issued","label":"Date","values":["1975-10"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Aston Pharmacy School"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["Aston University"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://publications.aston.ac.uk/id/eprint/10694/"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["doctoral"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["Ph.D."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://publications.aston.ac.uk/id/eprint/10694/1/190416_A_Brodrick_1975_reduced.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The methods available for the synthesis of pyrrolopyridines and the biological activity of the pyrrolo [2,3-b] pyridines are reviewed briefly. The reasons for the synthesis of pyrrolo [2. 3- b] pyridines from a pyrrole precursor are discussed and the possible routes from the available starting materials outlined. The synthesis of pyrrolo [2, 3-b] pyridines was approached by two main routes. The attempted syntheses of pyrroto|2,3-b] pyridines from 3-substitued 2-aminopyrroles are discussed and a possible explanation of the failure of these reactions is postulated. The preparation of a series of 2-amino-4-cyanopyrroles and their reaction with 1,3-dicarbonyl reagents to give pyrrolo [2. 3- b] pyridines: is discussed. The two-stage synthesis of pyrrolo[ 2, 3- b] pyridin-4 (7H)- ones from 2-amino-4-cyanopyrroles and diethyl ethoxymethylenemalonate is discussed. The preferred orientation of products obtained from the reaction between 2-amino-4-cyanopyrroles and unsymmetrical dicarbonyl reagents is discussed in terms of a reaction mechanism, The chemistry of the pyrrolo [2,3-3] pyridines is discussed. 13C nuclear magnetic resonance spectroscopy 1H-pyrrolo-[2.3-b] pyridine is discussed and the chemical shifts are rationalised in terms of electron density calculations. The 13C chemical shifts of 1H-pyrrolo[3,2-b] pyridine and 1H-pyrrolo [3,2-c] pyridine are compared with those of 1H-pyrrolo-[2:3-b] pyriaine. The 13C chemical shifts of a series of pyrrolo[2,3-b] pyridine derivatives are recorded, and a comparison of the chemical shift data with available data for methyl-substituted pyridines was made. The comparison of data established the product of the reaction between an aminopyrrole and 4,4-dimethoxybutan-2-one to be a 6-methylpyrrolo |2,3-b| pyridine and not a 4-methylpyrrolo [ 2,3~b] pyridine. The mass spectra of most of the compounds prepared in this work are recorded and possible fragmentation pathways are postulated."]},{"key":"dc:format","label":"Dc Format","values":["text"]},{"key":"dc:title","label":"Title","values":["Pyrrolo [2-3-b] Pyridines of Potential Chemotherapeutic Value"]}]}],"canonical_facts":{"dc:creator":["Brodrick, Andrew"],"dc:date":["1975-10"],"dc:date.issued":["1975-10"],"dc:description.abstract":["The methods available for the synthesis of pyrrolopyridines and the biological activity of the pyrrolo [2,3-b] pyridines are reviewed briefly. The reasons for the synthesis of pyrrolo [2. 3- b] pyridines from a pyrrole precursor are discussed and the possible routes from the available starting materials outlined. The synthesis of pyrrolo [2, 3-b] pyridines was approached by two main routes. The attempted syntheses of pyrroto|2,3-b] pyridines from 3-substitued 2-aminopyrroles are discussed and a possible explanation of the failure of these reactions is postulated. The preparation of a series of 2-amino-4-cyanopyrroles and their reaction with 1,3-dicarbonyl reagents to give pyrrolo [2. 3- b] pyridines: is discussed. The two-stage synthesis of pyrrolo[ 2, 3- b] pyridin-4 (7H)- ones from 2-amino-4-cyanopyrroles and diethyl ethoxymethylenemalonate is discussed. The preferred orientation of products obtained from the reaction between 2-amino-4-cyanopyrroles and unsymmetrical dicarbonyl reagents is discussed in terms of a reaction mechanism, The chemistry of the pyrrolo [2,3-3] pyridines is discussed. 13C nuclear magnetic resonance spectroscopy 1H-pyrrolo-[2.3-b] pyridine is discussed and the chemical shifts are rationalised in terms of electron density calculations. The 13C chemical shifts of 1H-pyrrolo[3,2-b] pyridine and 1H-pyrrolo [3,2-c] pyridine are compared with those of 1H-pyrrolo-[2:3-b] pyriaine. The 13C chemical shifts of a series of pyrrolo[2,3-b] pyridine derivatives are recorded, and a comparison of the chemical shift data with available data for methyl-substituted pyridines was made. The comparison of data established the product of the reaction between an aminopyrrole and 4,4-dimethoxybutan-2-one to be a 6-methylpyrrolo |2,3-b| pyridine and not a 4-methylpyrrolo [ 2,3~b] pyridine. The mass spectra of most of the compounds prepared in this work are recorded and possible fragmentation pathways are postulated."],"dc:format":["text"],"dc:identifier.uri":["https://publications.aston.ac.uk/id/eprint/10694/1/190416_A_Brodrick_1975_reduced.pdf"],"dc:publisher.department":["Aston Pharmacy School"],"dc:publisher.institution":["Aston University"],"dc:relation.isreferencedby":["https://publications.aston.ac.uk/id/eprint/10694/"],"dc:title":["Pyrrolo [2-3-b] Pyridines of Potential Chemotherapeutic Value"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["Ph.D."]},"updated_at":"2026-07-24T01:01:19Z"}