{"id":"https://openalex.org/W614893337","doi":"https://doi.org/10.1021/acs.joc.5b00614","title":"Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines","display_name":"Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines","publication_year":2015,"publication_date":"2015-06-09","ids":{"openalex":"https://openalex.org/W614893337","doi":"https://doi.org/10.1021/acs.joc.5b00614","mag":"614893337","pmid":"https://pubmed.ncbi.nlm.nih.gov/26056863"},"language":"en","primary_location":{"id":"doi:10.1021/acs.joc.5b00614","doi":"https://doi.org/10.1021/acs.joc.5b00614","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.5b00614","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"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/A5037938563","display_name":"Lam Quang Tran","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I1298838906","display_name":"Institut de Chimie des Substances Naturelles","ror":"https://ror.org/02st4q439","country_code":"FR","type":"facility","lineage":["https://openalex.org/I1294671590","https://openalex.org/I1298838906","https://openalex.org/I277688954"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Lam Quang Tran","raw_affiliation_strings":["Centre de Recherche de Gif,\rInstitut de Chimie des Substances Naturelles, Laboratoire International\rAssoci\u00e9, CNRS, 91198 Gif-sur-Yvette Cedex, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Centre de Recherche de Gif,\rInstitut de Chimie des Substances Naturelles, Laboratoire International\rAssoci\u00e9, CNRS, 91198 Gif-sur-Yvette Cedex, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I1298838906"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5071052943","display_name":"Jihui Li","orcid":"https://orcid.org/0000-0002-6859-3776","observed_orcids":["https://orcid.org/0000-0002-6859-3776"]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I1298838906","display_name":"Institut de Chimie des Substances Naturelles","ror":"https://ror.org/02st4q439","country_code":"FR","type":"facility","lineage":["https://openalex.org/I1294671590","https://openalex.org/I1298838906","https://openalex.org/I277688954"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Jihui Li","raw_affiliation_strings":["Centre de Recherche de Gif,\rInstitut de Chimie des Substances Naturelles, Laboratoire International\rAssoci\u00e9, CNRS, 91198 Gif-sur-Yvette Cedex, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Centre de Recherche de Gif,\rInstitut de Chimie des Substances Naturelles, Laboratoire International\rAssoci\u00e9, CNRS, 91198 Gif-sur-Yvette Cedex, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I1298838906"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5013360927","display_name":"Luc Neuville","orcid":"https://orcid.org/0000-0002-4648-2469","observed_orcids":["https://orcid.org/0000-0002-4648-2469"]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I1298838906","display_name":"Institut de Chimie des Substances Naturelles","ror":"https://ror.org/02st4q439","country_code":"FR","type":"facility","lineage":["https://openalex.org/I1294671590","https://openalex.org/I1298838906","https://openalex.org/I277688954"]}],"countries":["FR"],"is_corresponding":true,"raw_author_name":"Luc Neuville","raw_affiliation_strings":["Centre de Recherche de Gif,\rInstitut de Chimie des Substances Naturelles, Laboratoire International\rAssoci\u00e9, CNRS, 91198 Gif-sur-Yvette Cedex, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Centre de Recherche de Gif,\rInstitut de Chimie des Substances Naturelles, Laboratoire International\rAssoci\u00e9, CNRS, 91198 Gif-sur-Yvette Cedex, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I1298838906"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5013360927"],"corresponding_institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I1298838906"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.3703,"has_fulltext":false,"cited_by_count":27,"citation_normalized_percentile":{"value":0.77036096,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"80","issue":"12","first_page":"6102","last_page":"6108"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10817","display_name":"Multicomponent Synthesis of Heterocycles","score":0.38499999046325684,"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/T10817","display_name":"Multicomponent Synthesis of Heterocycles","score":0.38499999046325684,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.21960000693798065,"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/T12318","display_name":"Quinazolinone synthesis and applications","score":0.10639999806880951,"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/copper-catalysis","display_name":"copper catalysis","score":0.9559999704360962},{"id":"https://openalex.org/keywords/cascade-reactions","display_name":"cascade reactions","score":0.8109999895095825},{"id":"https://openalex.org/keywords/three-component-reaction","display_name":"three-component reaction","score":0.847000002861023},{"id":"https://openalex.org/keywords/2-aminobenzimidazole","display_name":"2-aminobenzimidazole","score":0.984000027179718},{"id":"https://openalex.org/keywords/cyanamide","display_name":"cyanamide","score":0.8930000066757202},{"id":"https://openalex.org/keywords/arylboronic-acids","display_name":"arylboronic acids","score":0.9950000047683716},{"id":"https://openalex.org/keywords/amines","display_name":"amines","score":0.8180000185966492},{"id":"https://openalex.org/keywords/oxidative-coupling","display_name":"oxidative coupling","score":0.6489999890327454},{"id":"https://openalex.org/keywords/c-h-functionalization","display_name":"C\u2013H functionalization","score":0.906000018119812},{"id":"https://openalex.org/keywords/c-n-bond-formation","display_name":"C\u2013N bond formation","score":0.7870000004768372},{"id":"https://openalex.org/keywords/heterocycle-synthesis","display_name":"heterocyclic synthesis","score":0.7889999747276306}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.951081395149231},{"id":"https://openalex.org/C2776416436","wikidata":"https://www.wikidata.org/wiki/Q3751781","display_name":"Domino","level":3,"score":0.7893226146697998},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.7056440114974976},{"id":"https://openalex.org/C544778455","wikidata":"https://www.wikidata.org/wiki/Q753","display_name":"Copper","level":2,"score":0.6952674984931946},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.5571757555007935},{"id":"https://openalex.org/C168167062","wikidata":"https://www.wikidata.org/wiki/Q1117970","display_name":"Component (thermodynamics)","level":2,"score":0.5445303320884705},{"id":"https://openalex.org/C115537861","wikidata":"https://www.wikidata.org/wiki/Q7645993","display_name":"Surface modification","level":2,"score":0.5276989936828613},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5083019137382507},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3333953320980072},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.3281813859939575},{"id":"https://openalex.org/C188027245","wikidata":"https://www.wikidata.org/wiki/Q750446","display_name":"Polymer chemistry","level":1,"score":0.3223368227481842},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C97355855","wikidata":"https://www.wikidata.org/wiki/Q11473","display_name":"Thermodynamics","level":1,"score":0.0},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000586","descriptor_name":"Amination","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001562","descriptor_name":"Benzimidazoles","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D001562","descriptor_name":"Benzimidazoles","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003300","descriptor_name":"Copper","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D011799","descriptor_name":"Quinazolines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011799","descriptor_name":"Quinazolines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.joc.5b00614","doi":"https://doi.org/10.1021/acs.joc.5b00614","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.5b00614","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:26056863","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/26056863","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of organic chemistry","raw_type":"Journal Article"},{"id":"pmh:oai:HAL:hal-01178968v1","doi":null,"is_oa":false,"landing_page_url":"https://hal.science/hal-01178968","pdf_url":null,"source":{"id":"https://openalex.org/S4306402512","display_name":"HAL","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4405252976","host_organization_name":"Centre pour la Communication Scientifique Directe","host_organization_lineage":["https://openalex.org/I4405252976"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Journal of Organic Chemistry, 2015, 80 (12), pp.6102-6108. &#x27E8;10.1021/acs.joc.5b00614&#x27E9;","raw_type":"info:eu-repo/semantics/article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320322892","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":79,"referenced_works":["https://openalex.org/W580825176","https://openalex.org/W1567523921","https://openalex.org/W1953270378","https://openalex.org/W1969003117","https://openalex.org/W1973503725","https://openalex.org/W1976591534","https://openalex.org/W1978170307","https://openalex.org/W1979427000","https://openalex.org/W1979646736","https://openalex.org/W1989212143","https://openalex.org/W1990380077","https://openalex.org/W1996442835","https://openalex.org/W1996562668","https://openalex.org/W1997157373","https://openalex.org/W2006947767","https://openalex.org/W2010115581","https://openalex.org/W2010224630","https://openalex.org/W2012548482","https://openalex.org/W2013581526","https://openalex.org/W2017538708","https://openalex.org/W2019169667","https://openalex.org/W2024983608","https://openalex.org/W2027518568","https://openalex.org/W2029131679","https://openalex.org/W2030523377","https://openalex.org/W2034009857","https://openalex.org/W2036344516","https://openalex.org/W2048986263","https://openalex.org/W2049694867","https://openalex.org/W2050864668","https://openalex.org/W2054284208","https://openalex.org/W2057086900","https://openalex.org/W2065047384","https://openalex.org/W2065393843","https://openalex.org/W2066956989","https://openalex.org/W2068749447","https://openalex.org/W2078861584","https://openalex.org/W2079509522","https://openalex.org/W2080459353","https://openalex.org/W2083790594","https://openalex.org/W2085196079","https://openalex.org/W2088150999","https://openalex.org/W2092683508","https://openalex.org/W2092695896","https://openalex.org/W2096614505","https://openalex.org/W2097186155","https://openalex.org/W2108240183","https://openalex.org/W2110478240","https://openalex.org/W2123101018","https://openalex.org/W2123203582","https://openalex.org/W2123771203","https://openalex.org/W2130505697","https://openalex.org/W2132626909","https://openalex.org/W2138749937","https://openalex.org/W2143885751","https://openalex.org/W2149164111","https://openalex.org/W2151439302","https://openalex.org/W2151665985","https://openalex.org/W2153859082","https://openalex.org/W2154212075","https://openalex.org/W2155390912","https://openalex.org/W2164023709","https://openalex.org/W2168631659","https://openalex.org/W2314107076","https://openalex.org/W2317744756","https://openalex.org/W2320065507","https://openalex.org/W2320142100","https://openalex.org/W2332059670","https://openalex.org/W2334412483","https://openalex.org/W2334618617","https://openalex.org/W2949081263","https://openalex.org/W2949764479","https://openalex.org/W2951146679","https://openalex.org/W2951360372","https://openalex.org/W2951830072","https://openalex.org/W2952218613","https://openalex.org/W2953291918","https://openalex.org/W3081548864","https://openalex.org/W4251038450"],"related_works":["https://openalex.org/W2950556430","https://openalex.org/W2965164146","https://openalex.org/W3213119162","https://openalex.org/W3016950184","https://openalex.org/W2092683508","https://openalex.org/W1792823354","https://openalex.org/W2012593212","https://openalex.org/W3134683306","https://openalex.org/W3038325674","https://openalex.org/W2896326529"],"abstract_inverted_index":{"A":[0],"copper-promoted":[1],"three-component":[2],"synthesis":[3],"of":[4,8,29,34,47,67],"2-aminobenzimidazoles":[5],"(1)":[6],"or":[7,50,55],"2-aminoquinazolines":[9],"(2)":[10],"involving":[11],"cyanamides,":[12,57],"arylboronic":[13],"acids,":[14],"and":[15,37,73],"amines":[16],"has":[17],"been":[18],"developed.":[19],"The":[20],"operationally":[21],"simple":[22],"oxidative":[23],"process,":[24,61],"performed":[25],"in":[26],"the":[27,44,62,65],"presence":[28],"K2CO3,":[30],"a":[31],"catalytic":[32],"amount":[33],"CuCl2\u00b72H2O,":[35],"2,2'-bipyridine,":[36],"an":[38,74],"O2":[39],"atmosphere":[40],"(1":[41],"atm),":[42],"allows":[43],"rapid":[45],"assembly":[46],"either":[48],"benzimidazoles":[49],"quinazolines":[51],"starting":[52],"from":[53,78],"aryl-":[54],"benzyl-substituted":[56],"respectively.":[58],"In":[59],"this":[60],"copper":[63],"promotes":[64],"formation":[66],"three":[68],"bonds,":[69,72],"two":[70],"C-N":[71],"additional":[75],"bond":[76],"resulting":[77],"C-H":[79],"functionalization":[80],"event.":[81]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":3},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":2},{"year":2020,"cited_by_count":3},{"year":2019,"cited_by_count":5},{"year":2018,"cited_by_count":3},{"year":2017,"cited_by_count":3},{"year":2016,"cited_by_count":2},{"year":2015,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
