{"id":"https://openalex.org/W2950177113","doi":"https://doi.org/10.1021/jo3018632","title":"1-Alkyl- and (\u00b1)-1,2-Dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones by a Tandem Michael\u2013SNAr Annulation Reaction","display_name":"1-Alkyl- and (\u00b1)-1,2-Dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones by a Tandem Michael\u2013SNAr Annulation Reaction","publication_year":2012,"publication_date":"2012-10-31","ids":{"openalex":"https://openalex.org/W2950177113","doi":"https://doi.org/10.1021/jo3018632","mag":"2950177113","pmid":"https://pubmed.ncbi.nlm.nih.gov/23113469"},"language":"en","primary_location":{"id":"doi:10.1021/jo3018632","doi":"https://doi.org/10.1021/jo3018632","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo3018632","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/A5079371014","display_name":"Richard A. Bunce","orcid":"https://orcid.org/0009-0003-7927-5655","observed_orcids":["https://orcid.org/0009-0003-7927-5655"]},"institutions":[{"id":"https://openalex.org/I115475287","display_name":"Oklahoma State University","ror":"https://ror.org/01g9vbr38","country_code":"US","type":"education","lineage":["https://openalex.org/I115475287"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Richard A. Bunce","raw_affiliation_strings":["Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States","institution_ids":["https://openalex.org/I115475287"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5062966886","display_name":"Scott T. Squires","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I115475287","display_name":"Oklahoma State University","ror":"https://ror.org/01g9vbr38","country_code":"US","type":"education","lineage":["https://openalex.org/I115475287"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Scott T. Squires","raw_affiliation_strings":["Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States","institution_ids":["https://openalex.org/I115475287"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5045195821","display_name":"Baskar Nammalwar","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I115475287","display_name":"Oklahoma State University","ror":"https://ror.org/01g9vbr38","country_code":"US","type":"education","lineage":["https://openalex.org/I115475287"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Baskar Nammalwar","raw_affiliation_strings":["Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States","institution_ids":["https://openalex.org/I115475287"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5079371014"],"corresponding_institution_ids":["https://openalex.org/I115475287"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.0302,"has_fulltext":false,"cited_by_count":15,"citation_normalized_percentile":{"value":0.73804852,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":94,"max":97},"biblio":{"volume":"78","issue":"5","first_page":"2144","last_page":"2148"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13208","display_name":"Synthesis of heterocyclic compounds","score":0.6172000169754028,"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":0.6172000169754028,"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":0.10170000046491623,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.09830000251531601,"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/michael-addition","display_name":"Michael addition","score":0.7749999761581421},{"id":"https://openalex.org/keywords/nucleophilic-aromatic-substitution","display_name":"nucleophilic aromatic substitution","score":0.8759999871253967},{"id":"https://openalex.org/keywords/alpha-beta-unsaturated-ketones","display_name":"\u03b1,\u03b2-unsaturated ketones","score":0.48500001430511475},{"id":"https://openalex.org/keywords/pyridine-derivatives","display_name":"pyridine derivatives","score":0.5709999799728394},{"id":"https://openalex.org/keywords/reaction-mechanism","display_name":"reaction mechanism","score":0.7120000123977661}],"concepts":[{"id":"https://openalex.org/C7512685","wikidata":"https://www.wikidata.org/wiki/Q529093","display_name":"Annulation","level":3,"score":0.9050870537757874},{"id":"https://openalex.org/C2777814067","wikidata":"https://www.wikidata.org/wiki/Q1752317","display_name":"Tandem","level":2,"score":0.7820867300033569},{"id":"https://openalex.org/C112423150","wikidata":"https://www.wikidata.org/wiki/Q642233","display_name":"Michael reaction","level":3,"score":0.6182162761688232},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.6130203008651733},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5618764758110046},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4952923357486725},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.21484032273292542},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.11497953534126282},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.07677814364433289},{"id":"https://openalex.org/C159985019","wikidata":"https://www.wikidata.org/wiki/Q181790","display_name":"Composite material","level":1,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/jo3018632","doi":"https://doi.org/10.1021/jo3018632","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo3018632","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:23113469","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/23113469","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":20,"referenced_works":["https://openalex.org/W620132579","https://openalex.org/W1538938881","https://openalex.org/W1981054724","https://openalex.org/W1983152958","https://openalex.org/W1993001765","https://openalex.org/W1995599191","https://openalex.org/W2014137278","https://openalex.org/W2027554115","https://openalex.org/W2044897150","https://openalex.org/W2069607377","https://openalex.org/W2075859545","https://openalex.org/W2077283531","https://openalex.org/W2086469125","https://openalex.org/W2110171006","https://openalex.org/W2330393308","https://openalex.org/W2950271440","https://openalex.org/W2950885393","https://openalex.org/W2951238613","https://openalex.org/W2953363504","https://openalex.org/W4250812124"],"related_works":["https://openalex.org/W2000309124","https://openalex.org/W2075859545","https://openalex.org/W2738710043","https://openalex.org/W1981054724","https://openalex.org/W2254559812","https://openalex.org/W2077900533","https://openalex.org/W2110171006","https://openalex.org/W1977746049","https://openalex.org/W2949708053","https://openalex.org/W4206422578"],"abstract_inverted_index":{"A":[0],"tandem":[1],"Michael-S(N)Ar":[2],"annulation":[3],"reaction":[4,48],"has":[5],"been":[6],"developed":[7],"for":[8,35],"the":[9,47,56],"synthesis":[10],"of":[11,16],"1-alkyl":[12],"and":[13],"(\u00b1)-1,2-dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones.":[14],"Treatment":[15],"1-(2-chloropyridin-3-yl)prop-2-en-1-one":[17],"(R":[18,25],"=":[19,26],"H)":[20],"or":[21,23],"(E":[22],"Z)-1-(2-chloropyridin-3-yl)but-2-en-1-one":[24],"CH3)":[27],"with":[28],"R'NH2":[29],"in":[30,40],"DMF":[31],"at":[32],"50":[33],"\u00b0C":[34],"24":[36],"h":[37],"provides":[38],"2,3-dihydro-1,8-naphthyridin-4(1H)-ones":[39],"65-85%":[41],"yields.":[42],"Mechanistic":[43],"studies":[44],"suggest":[45],"that":[46],"sequence":[49],"is":[50],"initiated":[51],"by":[52],"Michael":[53],"addition":[54],"to":[55],"side":[57],"chain":[58],"enone.":[59]},"counts_by_year":[{"year":2024,"cited_by_count":3},{"year":2021,"cited_by_count":3},{"year":2016,"cited_by_count":2},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":3}],"updated_date":"2026-08-21T09:56:20.448147","created_date":"2019-06-27T00:00:00"}
