{"id":{"repo_id":"vilnius","oai_identifier":"oai:vu.lt:elaba:1938053"},"canonical_url":"https://search.dev.ndltd.org/etd/vilnius/oai:vu.lt:elaba:1938053","repository":{"repo_id":"vilnius","name":"Vilnius University","base_url":"https://epublications.vu.lt/oai"},"display":{"title":"Alkilintų 5-cian-2-metilsulfanil-4(3H)-pirimidinonų sintezės ir ciklizacijos reakcijų tyrimas /","abstract":"The cyclization reactions of initial ethyl (E)-2-cyano-3-(S-methylisothioureido)-2-propenoate under acid and basic catalysis conditions has been studied. It was determined that boiling in glacial acetic acid proceeds selectively and leads to formation of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate, while ring closure in alkaline media gives rise to a mixture of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone (major product), small amounts of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate and uncyclisized products – ethyl 2-cyano-3-ureido-2-propenoates. Alkylation of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone with 4-substituted ω- bromoacetophenones in the system CH3CN–K2CO3–[KI] has been investigated and influence of aromatic ring substituent for alkylation product distribution has been determined. The all three series of O-, N3- and N1-alkylated isomers have been isolated by means of fraction crystallization. Novel method for the synthesis of furo[2,3-d]pyrimidines by cyclization of of O-alkylated isomers – 2-methylsulfanyl-4-(4´-R-phenacyloxy)pyrimidine-5-carbonitriles – has been developed and functionalization (acetylation, oxidation, hydrolysis and hydrazinolysis) possibilities of synthesized 5-amino-6-(4´-R-benzoyl)-2-methylsulfanylfuro[2,3-d]pyrimidines has been examined.","abstract_html":"The cyclization reactions of initial ethyl (E)-2-cyano-3-(S-methylisothioureido)-2-propenoate under acid and basic catalysis conditions has been studied. It was determined that boiling in glacial acetic acid proceeds selectively and leads to formation of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate, while ring closure in alkaline media gives rise to a mixture of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone (major product), small amounts of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate and uncyclisized products – ethyl 2-cyano-3-ureido-2-propenoates. Alkylation of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone with 4-substituted ω- bromoacetophenones in the system CH3CN–K2CO3–[KI] has been investigated and influence of aromatic ring substituent for alkylation product distribution has been determined. The all three series of O-, N3- and N1-alkylated isomers have been isolated by means of fraction crystallization. Novel method for the synthesis of furo[2,3-d]pyrimidines by cyclization of of O-alkylated isomers – 2-methylsulfanyl-4-(4´-R-phenacyloxy)pyrimidine-5-carbonitriles – has been developed and functionalization (acetylation, oxidation, hydrolysis and hydrazinolysis) possibilities of synthesized 5-amino-6-(4´-R-benzoyl)-2-methylsulfanylfuro[2,3-d]pyrimidines has been examined.","abstract_has_math":false,"creators":["Stankevičiūtė, Živilė,"],"institution":"Institutional Repository of Vilnius University","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Malinauskas, Albertas"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2010,"date_issued":"2010","date_published":"2010","updated_at":"2026-07-24T05:55:35Z","subjects":["4(3H)pyrimidinone ; alkylation ; furo[2 ; 3-d]pyrimidine ; cyclization"],"languages":["lit"],"rights":["info:eu-repo/semantics/openAccess"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://repository.vu.lt/VU:ELABAETD1938053&prefLang=en_US","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Malinauskas, Albertas"]},{"key":"dc:creator","label":"Author","values":["Stankevičiūtė, Živilė,"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2010"]},{"key":"dc:publisher","label":"Institution","values":["Institutional Repository of Vilnius University"]},{"key":"dc:relation","label":"Dc Relation","values":["https://epublications.vu.lt/object/elaba:1938053/1938053.pdf"]},{"key":"dc:type","label":"Dc Type","values":["info:eu-repo/semantics/doctoralThesis"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["4(3H)pyrimidinone ; alkylation ; furo[2 ; 3-d]pyrimidine ; cyclization"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["lit"]},{"key":"dc:rights","label":"Dc Rights","values":["info:eu-repo/semantics/openAccess"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://repository.vu.lt/VU:ELABAETD1938053&prefLang=en_US"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The cyclization reactions of initial ethyl (E)-2-cyano-3-(S-methylisothioureido)-2-propenoate under acid and basic catalysis conditions has been studied. It was determined that boiling in glacial acetic acid proceeds selectively and leads to formation of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate, while ring closure in alkaline media gives rise to a mixture of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone (major product), small amounts of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate and uncyclisized products – ethyl 2-cyano-3-ureido-2-propenoates. Alkylation of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone with 4-substituted ω- bromoacetophenones in the system CH3CN–K2CO3–[KI] has been investigated and influence of aromatic ring substituent for alkylation product distribution has been determined. The all three series of O-, N3- and N1-alkylated isomers have been isolated by means of fraction crystallization. Novel method for the synthesis of furo[2,3-d]pyrimidines by cyclization of of O-alkylated isomers – 2-methylsulfanyl-4-(4´-R-phenacyloxy)pyrimidine-5-carbonitriles – has been developed and functionalization (acetylation, oxidation, hydrolysis and hydrazinolysis) possibilities of synthesized 5-amino-6-(4´-R-benzoyl)-2-methylsulfanylfuro[2,3-d]pyrimidines has been examined."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Alkilintų 5-cian-2-metilsulfanil-4(3H)-pirimidinonų sintezės ir ciklizacijos reakcijų tyrimas /","Studies on the synthesis and cyclization reactions of alkylated 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinones."]}]}],"canonical_facts":{"dc:contributor":["Malinauskas, Albertas"],"dc:creator":["Stankevičiūtė, Živilė,"],"dc:date":["2010"],"dc:description":["The cyclization reactions of initial ethyl (E)-2-cyano-3-(S-methylisothioureido)-2-propenoate under acid and basic catalysis conditions has been studied. It was determined that boiling in glacial acetic acid proceeds selectively and leads to formation of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate, while ring closure in alkaline media gives rise to a mixture of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone (major product), small amounts of ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate and uncyclisized products – ethyl 2-cyano-3-ureido-2-propenoates. Alkylation of 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinone with 4-substituted ω- bromoacetophenones in the system CH3CN–K2CO3–[KI] has been investigated and influence of aromatic ring substituent for alkylation product distribution has been determined. The all three series of O-, N3- and N1-alkylated isomers have been isolated by means of fraction crystallization. Novel method for the synthesis of furo[2,3-d]pyrimidines by cyclization of of O-alkylated isomers – 2-methylsulfanyl-4-(4´-R-phenacyloxy)pyrimidine-5-carbonitriles – has been developed and functionalization (acetylation, oxidation, hydrolysis and hydrazinolysis) possibilities of synthesized 5-amino-6-(4´-R-benzoyl)-2-methylsulfanylfuro[2,3-d]pyrimidines has been examined."],"dc:format":["application/pdf"],"dc:identifier":["https://repository.vu.lt/VU:ELABAETD1938053&prefLang=en_US"],"dc:language":["lit"],"dc:publisher":["Institutional Repository of Vilnius University"],"dc:relation":["https://epublications.vu.lt/object/elaba:1938053/1938053.pdf"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:subject":["4(3H)pyrimidinone ; alkylation ; furo[2 ; 3-d]pyrimidine ; cyclization"],"dc:title":["Alkilintų 5-cian-2-metilsulfanil-4(3H)-pirimidinonų sintezės ir ciklizacijos reakcijų tyrimas /","Studies on the synthesis and cyclization reactions of alkylated 5-cyano-2-methylsulfanyl-4(3H)-pyrimidinones."],"dc:type":["info:eu-repo/semantics/doctoralThesis"]},"updated_at":"2026-07-24T05:55:35Z"}