{"id":"https://openalex.org/W2950183758","doi":"https://doi.org/10.3987/com-14-13058","title":"A Simple Synthesis of 4-Hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione Derivatives by the Reaction of 3-Isothiocyanatopyridin-4-yl Ketones with Primary Amines","display_name":"A Simple Synthesis of 4-Hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione Derivatives by the Reaction of 3-Isothiocyanatopyridin-4-yl Ketones with Primary Amines","publication_year":2014,"publication_date":"2014-01-01","ids":{"openalex":"https://openalex.org/W2950183758","doi":"https://doi.org/10.3987/com-14-13058","mag":"2950183758"},"language":"en","primary_location":{"id":"doi:10.3987/com-14-13058","doi":"https://doi.org/10.3987/com-14-13058","is_oa":false,"landing_page_url":"https://doi.org/10.3987/com-14-13058","pdf_url":null,"source":{"id":"https://openalex.org/S27298842","display_name":"Heterocycles","issn_l":"0385-5414","issn":["0385-5414","1881-0942"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-1","norway-1","poland-40","russia-white-list-4"],"host_organization":"https://openalex.org/P4310320990","host_organization_name":"Elsevier BV","host_organization_lineage":["https://openalex.org/P4310320990"],"host_organization_lineage_names":["Elsevier BV"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"HETEROCYCLES","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5074727414","display_name":"Kazuhiro Kobayashi","orcid":"https://orcid.org/0000-0002-3366-3586","observed_orcids":["https://orcid.org/0000-0002-3366-3586","https://orcid.org/0009-0003-9664-7756"]},"institutions":[{"id":"https://openalex.org/I4588055","display_name":"Tottori University","ror":"https://ror.org/024yc3q36","country_code":"JP","type":"education","lineage":["https://openalex.org/I4588055"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Kazuhiro Kobayashi","raw_affiliation_strings":["Division of Applied Chemistry, Department of Chemistry and Biotechnology,","Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Applied Chemistry, Department of Chemistry and Biotechnology,","institution_ids":[]},{"raw_affiliation_string":"Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;","institution_ids":["https://openalex.org/I4588055"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5074008092","display_name":"Hiroki Inouchi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4588055","display_name":"Tottori University","ror":"https://ror.org/024yc3q36","country_code":"JP","type":"education","lineage":["https://openalex.org/I4588055"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hiroki Inouchi","raw_affiliation_strings":["Division of Applied Chemistry, Department of Chemistry and Biotechnology,","Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Applied Chemistry, Department of Chemistry and Biotechnology,","institution_ids":[]},{"raw_affiliation_string":"Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;","institution_ids":["https://openalex.org/I4588055"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5012107271","display_name":"Manami Konishi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4588055","display_name":"Tottori University","ror":"https://ror.org/024yc3q36","country_code":"JP","type":"education","lineage":["https://openalex.org/I4588055"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Manami Konishi","raw_affiliation_strings":["Division of Applied Chemistry, Department of Chemistry and Biotechnology,","Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Applied Chemistry, Department of Chemistry and Biotechnology,","institution_ids":[]},{"raw_affiliation_string":"Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;","institution_ids":["https://openalex.org/I4588055"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I4588055"],"apc_list":null,"apc_paid":null,"fwci":0.1357,"has_fulltext":false,"cited_by_count":3,"citation_normalized_percentile":{"value":0.48610976,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":"89","issue":"9","first_page":"2168","last_page":"2168"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13208","display_name":"Synthesis of heterocyclic compounds","score":0.9473000168800354,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T13208","display_name":"Synthesis of heterocyclic compounds","score":0.9473000168800354,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T14099","display_name":"Synthesis and Characterization of Heterocyclic Compounds","score":0.020899999886751175,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13304","display_name":"Synthesis and Reactivity of Sulfur-Containing Compounds","score":0.010999999940395355,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/3-aminopyridine","display_name":"3-aminopyridine","score":0.828000009059906},{"id":"https://openalex.org/keywords/primary-amines","display_name":"primary amines","score":0.8700000047683716},{"id":"https://openalex.org/keywords/fused-heterocycles","display_name":"fused heterocycles","score":0.7429999709129333}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9653356075286865},{"id":"https://openalex.org/C2779321679","wikidata":"https://www.wikidata.org/wiki/Q207722","display_name":"Pyrimidine","level":2,"score":0.8162598013877869},{"id":"https://openalex.org/C2777977315","wikidata":"https://www.wikidata.org/wiki/Q7243056","display_name":"Primary (astronomy)","level":2,"score":0.7388008832931519},{"id":"https://openalex.org/C2780586882","wikidata":"https://www.wikidata.org/wiki/Q7520643","display_name":"Simple (philosophy)","level":2,"score":0.4850008189678192},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.47563791275024414},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4450332224369049},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.35483992099761963},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.23328205943107605},{"id":"https://openalex.org/C111472728","wikidata":"https://www.wikidata.org/wiki/Q9471","display_name":"Epistemology","level":1,"score":0.0},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C138885662","wikidata":"https://www.wikidata.org/wiki/Q5891","display_name":"Philosophy","level":0,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.3987/com-14-13058","doi":"https://doi.org/10.3987/com-14-13058","is_oa":false,"landing_page_url":"https://doi.org/10.3987/com-14-13058","pdf_url":null,"source":{"id":"https://openalex.org/S27298842","display_name":"Heterocycles","issn_l":"0385-5414","issn":["0385-5414","1881-0942"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-1","norway-1","poland-40","russia-white-list-4"],"host_organization":"https://openalex.org/P4310320990","host_organization_name":"Elsevier BV","host_organization_lineage":["https://openalex.org/P4310320990"],"host_organization_lineage_names":["Elsevier BV"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"HETEROCYCLES","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W1988019773","https://openalex.org/W2952282059","https://openalex.org/W2145666555","https://openalex.org/W2552534219","https://openalex.org/W1985351009","https://openalex.org/W1983312140","https://openalex.org/W2034228849","https://openalex.org/W2951123604","https://openalex.org/W1550079299","https://openalex.org/W2130650344"],"abstract_inverted_index":{"The":[0],"reaction":[1,135],"of":[2,50,92,104,126,149],"aryl(3-isothiocyanatopyridin-4-yl)methanones,":[3],"prepared":[4,117],"easily":[5,116],"from":[6,165],"commercially":[7,120],"available":[8,121],"3-aminopyridine,":[9],"with":[10,38,119,136],"primary":[11,137],"amines":[12,138],"at":[13],"room":[14],"temperature":[15],"afforded":[16],"3-substituted":[17,141],"4-aryl-4-hydroxy-3,4dihydropyrido":[18],"[3,4-d]pyrimidine-2(1H)-thiones":[19],"in":[20,45],"good":[21],"yields.These":[22],"ketones":[23],"could":[24],"be":[25,115],"converted":[26],"to":[27,64,73,129,158],"new":[28],"tricyclic":[29],"heterocyclic":[30,77],"systems,":[31],"2,3-dihydro-5Hpyrido":[32],"[3,4-d]thiazolo[3,2-a]pyrimidine":[33],"and":[34,41,69,107,133,163],"3,4-dihydro-2H,6H-pyrido[3',4':4,5]pyrimido[2,1-b][1,3]thiazine,":[35],"upon":[36],"treatment":[37],"2-bromoethanamine":[39],"hydrobromide":[40],"3-bromopropaneamine":[42],"hydrobromide,":[43],"respectively,":[44],"the":[46,89,96,130,147],"presence":[47],"two":[48],"equivalents":[49],"triethylamine.3,4-Dihydropyrido[3,4-d]pyrimidine-2(1H)-thione":[51],"derivatives":[52,109,161],"are":[53],"interesting":[54],"heterocycles,":[55],"because":[56],"some":[57],"compounds":[58],"having":[59],"this":[60],"structure":[61],"have":[62,70,83,100,168],"reported":[63],"exhibit":[65],"biological":[66],"activity":[67],"1":[68],"been":[71,84],"elaborated":[72],"more":[74],"complex":[75],"fused":[76],"systems.":[78],"2":[79],"However,":[80],"no":[81],"reports":[82],"so":[85],"far":[86],"recorded":[87],"for":[88],"general":[90],"preparation":[91],"3,4-dihydropyrido":[93,159],"[3,4-d]pyrimidine-2(1H)-thione":[94,160],"derivatives.On":[95],"other":[97],"hand,":[98],"we":[99],"recently":[101],"described":[102],"syntheses":[103],"1,7-naphthyridine":[105],"3a":[106],"3H-pyrrolo[2,3-c]pyridin-3-ol":[108],"3b":[110],"utilizing":[111],"aryl(3-isocyanopyridin-4-yl)methanones,":[112],"which":[113,152],"can":[114],"starting":[118],"3-aminopyridine.We":[122],"envisaged":[123],"that":[124,171],"conversion":[125],"these":[127],"isocyanides":[128],"corresponding":[131],"isothiocyanates":[132],"their":[134],"would":[139],"give":[140],"4-aryl-4-hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thiones.":[142],"4":[143],"This":[144],"paper":[145],"describes":[146],"results":[148],"our":[150],"study,":[151],"provide":[153],"a":[154],"facile":[155],"synthetic":[156],"entry":[157],"(2)":[162],"(3)":[164],"aryl(3-isothiocyanatopyridin-4-yl)methanones":[166],"(1).We":[167],"also":[169],"found":[170],"2168":[172]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2015,"cited_by_count":1}],"updated_date":"2026-11-05T12:25:35.769452","created_date":"2019-06-27T00:00:00"}