{"id":"https://openalex.org/W2950126625","doi":"https://doi.org/10.3987/com-92-s1","title":"Regioselective ortho-Lithiation of Halopyridines. Syntheses of ortho-Disubstituted Pyridines and a Convenient Generations of 3,4-Pyridyne","display_name":"Regioselective ortho-Lithiation of Halopyridines. Syntheses of ortho-Disubstituted Pyridines and a Convenient Generations of 3,4-Pyridyne","publication_year":1993,"publication_date":"1993-01-01","ids":{"openalex":"https://openalex.org/W2950126625","doi":"https://doi.org/10.3987/com-92-s1","mag":"2950126625"},"language":"en","primary_location":{"id":"doi:10.3987/com-92-s1","doi":"https://doi.org/10.3987/com-92-s1","is_oa":false,"landing_page_url":"https://doi.org/10.3987/com-92-s1","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","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/A5049245360","display_name":"Gordon W. Gribble","orcid":"https://orcid.org/0000-0002-7573-0927","observed_orcids":["https://orcid.org/0000-0002-7573-0927"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Gordon W. Gribble","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5003544584","display_name":"Mark G. Saulnier","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Mark G. Saulnier","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":1.8256,"has_fulltext":false,"cited_by_count":66,"citation_normalized_percentile":{"value":0.83516928,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"35","issue":"1","first_page":"151","last_page":"151"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9970999956130981,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9970999956130981,"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/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.0017000000225380063,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.00019999999494757503,"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/halopyridines","display_name":"halopyridines","score":0.984000027179718},{"id":"https://openalex.org/keywords/lithium-diisopropylamide","display_name":"lithium diisopropylamide","score":0.9390000104904175},{"id":"https://openalex.org/keywords/metal-halogen-exchange","display_name":"halogen-metal exchange","score":0.9279999732971191},{"id":"https://openalex.org/keywords/n-butyllithium","display_name":"n-butyllithium","score":0.9679999947547913},{"id":"https://openalex.org/keywords/diels-alder-reaction","display_name":"Diels-Alder reaction","score":0.9769999980926514},{"id":"https://openalex.org/keywords/furan","display_name":"furan","score":0.9440000057220459},{"id":"https://openalex.org/keywords/2-5-dimethylfuran","display_name":"2,5-dimethylfuran","score":0.9800000190734863}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9581491351127625},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.8918865323066711},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.49073684215545654},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.39232319593429565},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3458518385887146},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2950589060783386},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.3987/com-92-s1","doi":"https://doi.org/10.3987/com-92-s1","is_oa":false,"landing_page_url":"https://doi.org/10.3987/com-92-s1","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/W2090051601","https://openalex.org/W2028707695","https://openalex.org/W1970108937","https://openalex.org/W2015735287","https://openalex.org/W7095238053","https://openalex.org/W2049333371","https://openalex.org/W1989694766","https://openalex.org/W2069686342","https://openalex.org/W1989872692","https://openalex.org/W2410622327"],"abstract_inverted_index":{"me":[0],"regioselective":[1],"onho-lithiation":[2],"of":[3,44,75,100,135,142,159,172],"3-chlm":[4],"(4),":[5],"3-fluoro-(7).3":[6],"-h":[7],"m":[8],"o":[9],"-(lo),":[10],"2chloro":[11],"(22).and":[12],"4-chlmpyridine":[13],"(25)":[14],"with":[15,21,53,91,127,176],"lithium":[16],"diisopropylamide":[17],"affords,":[18],"after":[19],"quenching":[20],"various":[22],"electrophiles,":[23],"the":[24,71,79,96,117,140,143,150,157],"corresponding":[25],"onho-disubstih~ted":[26],"pyridines":[27],"in":[28,49,111,149,170],"yields":[29],"from":[30,180],"16-9696.Halogen-metal":[31],"exchange":[32],"between":[33],"4-i&3-chlmpyridine":[34],"(6a)":[35],"and":[36,55,60,73,87,107,123,178],"ten-butyllithium":[37],"or":[38],"n-butyllithium":[39],"provides":[40],"a":[41,50,67,92,112,181],"wnvenient":[42],"generation":[43,158],"3.4-pyridyne":[45],"(1).which":[46],"is":[47,164],"trapped":[48],"Diels-Alder":[51,113],"reaction":[52],"furan":[54],"2.5-dimethylfuran":[56],"to":[57,95,105],"give":[58],"31":[59],"32":[61],"(2438%).Heteroatom-facilitated":[62],"metalation":[63],"reactions":[64,84],"have":[65,147],"had":[66],"major":[68],"impact":[69],"on":[70],"design":[72],"execution":[74],"organic":[76],"synthesis":[77],"over":[78],"past":[80],"decade,":[81],"particularly":[82],"those":[83],"involving":[85],"aromatic":[86],"heternaromatic":[88],"subsh'ates.'.'In":[89],"co~ection":[90],"synthetic":[93],"approach":[94],"ellipticine":[97],"(6H-pyrido[4,3-b]carbmle)":[98],"family":[99],"antitumor":[101],"alkaloids,":[102],"we":[103],"desired":[104],"generate":[106],"uap":[108],"3,4-pyridyne":[109],"(1)":[110],"reaction.3At":[114],"that":[115],"time,":[116],"only":[118],"two":[119],"techniques":[120],"for":[121,156],"generating":[122],"efficiently":[124],"trapping":[125],"1":[126],"dienes":[128],"(e.g.,":[129],"fwan)":[130],"involved":[131],"tedious,":[132],"multi-step":[133],"syntheses":[134],"33pyridyne":[136],"precursorsf":[137],"5":[138],"Following":[139],"completion":[141],"present":[144],"research,":[145],"there":[146],"appeared":[148],"literature":[151],"several":[152],"other":[153],"good":[154],"methods":[155],"3,dpyridyne":[160],"(1)6":[161],"t~his":[162],"papx":[163],"dedicated":[165],"lo":[166],"Professor":[167],"Ted":[168],"Taylor":[169],"celebration":[171],"his":[173],"70th":[174],"birthday,":[175],"affection":[177],"admimion":[179],"fellow":[182],"Vermonter.":[183]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":1},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":3},{"year":2019,"cited_by_count":2},{"year":2017,"cited_by_count":1},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":3},{"year":2012,"cited_by_count":2}],"updated_date":"2026-11-05T12:25:35.769452","created_date":"2019-06-27T00:00:00"}