{"id":"https://openalex.org/W3203837618","doi":"https://doi.org/10.1002/slct.202102576","title":"Unexpected Intramolecular Phosphite\u2010Mediated Amide Coupling To Yield 3,5\u2010Dioxo\u20101\u2010Piperazines","display_name":"Unexpected Intramolecular Phosphite\u2010Mediated Amide Coupling To Yield 3,5\u2010Dioxo\u20101\u2010Piperazines","publication_year":2021,"publication_date":"2021-09-23","ids":{"openalex":"https://openalex.org/W3203837618","doi":"https://doi.org/10.1002/slct.202102576","mag":"3203837618"},"language":"en","primary_location":{"id":"doi:10.1002/slct.202102576","doi":"https://doi.org/10.1002/slct.202102576","is_oa":true,"landing_page_url":"https://doi.org/10.1002/slct.202102576","pdf_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202102576","source":{"id":"https://openalex.org/S4210221416","display_name":"ChemistrySelect","issn_l":"2365-6549","issn":["2365-6549"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-1","ki-jl-1","norway-1","poland-40","russia-white-list-2","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"ChemistrySelect","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202102576","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5040020590","display_name":"Philipp Heim","orcid":"https://orcid.org/0000-0002-6316-1544","observed_orcids":["https://orcid.org/0000-0002-6316-1544"]},"institutions":[{"id":"https://openalex.org/I205274468","display_name":"Trinity College Dublin","ror":"https://ror.org/02tyrky19","country_code":"IE","type":"education","lineage":["https://openalex.org/I205274468"]},{"id":"https://openalex.org/I4210112033","display_name":"Advanced Materials and BioEngineering Research","ror":"https://ror.org/01c4rxk68","country_code":"IE","type":"facility","lineage":["https://openalex.org/I142762351","https://openalex.org/I188760350","https://openalex.org/I205274468","https://openalex.org/I230495080","https://openalex.org/I27577105","https://openalex.org/I4210112033","https://openalex.org/I42934936"]}],"countries":["IE"],"is_corresponding":false,"raw_author_name":"Philipp Heim","raw_affiliation_strings":["School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland","institution_ids":["https://openalex.org/I205274468","https://openalex.org/I4210112033"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5007312741","display_name":"Brendan Twamley","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I205274468","display_name":"Trinity College Dublin","ror":"https://ror.org/02tyrky19","country_code":"IE","type":"education","lineage":["https://openalex.org/I205274468"]},{"id":"https://openalex.org/I4210112033","display_name":"Advanced Materials and BioEngineering Research","ror":"https://ror.org/01c4rxk68","country_code":"IE","type":"facility","lineage":["https://openalex.org/I142762351","https://openalex.org/I188760350","https://openalex.org/I205274468","https://openalex.org/I230495080","https://openalex.org/I27577105","https://openalex.org/I4210112033","https://openalex.org/I42934936"]}],"countries":["IE"],"is_corresponding":false,"raw_author_name":"Brendan Twamley","raw_affiliation_strings":["School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland","institution_ids":["https://openalex.org/I205274468","https://openalex.org/I4210112033"]}]},{"author_position":"middle","author":{"id":null,"display_name":"John O'Brien","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I205274468","display_name":"Trinity College Dublin","ror":"https://ror.org/02tyrky19","country_code":"IE","type":"education","lineage":["https://openalex.org/I205274468"]},{"id":"https://openalex.org/I4210112033","display_name":"Advanced Materials and BioEngineering Research","ror":"https://ror.org/01c4rxk68","country_code":"IE","type":"facility","lineage":["https://openalex.org/I142762351","https://openalex.org/I188760350","https://openalex.org/I205274468","https://openalex.org/I230495080","https://openalex.org/I27577105","https://openalex.org/I4210112033","https://openalex.org/I42934936"]}],"countries":["IE"],"is_corresponding":false,"raw_author_name":"John O'Brien","raw_affiliation_strings":["School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland","institution_ids":["https://openalex.org/I205274468","https://openalex.org/I4210112033"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5054670336","display_name":"Aidan R. McDonald","orcid":"https://orcid.org/0000-0002-8930-3256","observed_orcids":["https://orcid.org/0000-0002-8930-3256"]},"institutions":[{"id":"https://openalex.org/I205274468","display_name":"Trinity College Dublin","ror":"https://ror.org/02tyrky19","country_code":"IE","type":"education","lineage":["https://openalex.org/I205274468"]},{"id":"https://openalex.org/I4210112033","display_name":"Advanced Materials and BioEngineering Research","ror":"https://ror.org/01c4rxk68","country_code":"IE","type":"facility","lineage":["https://openalex.org/I142762351","https://openalex.org/I188760350","https://openalex.org/I205274468","https://openalex.org/I230495080","https://openalex.org/I27577105","https://openalex.org/I4210112033","https://openalex.org/I42934936"]}],"countries":["IE"],"is_corresponding":true,"raw_author_name":"Aidan R. McDonald","raw_affiliation_strings":["School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"School of Chemistry and CRANN/AMBER Nanoscience Institute, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland","institution_ids":["https://openalex.org/I205274468","https://openalex.org/I4210112033"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5054670336"],"corresponding_institution_ids":["https://openalex.org/I205274468","https://openalex.org/I4210112033"],"apc_list":{"value":3500,"currency":"USD","value_usd":3500},"apc_paid":{"value":3500,"currency":"USD","value_usd":3500},"fwci":0.099,"has_fulltext":false,"cited_by_count":1,"citation_normalized_percentile":{"value":0.28831781,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":94},"biblio":{"volume":"6","issue":"36","first_page":"9663","last_page":"9668"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11748","display_name":"Organophosphorus compounds synthesis","score":0.5913000106811523,"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/T11748","display_name":"Organophosphorus compounds synthesis","score":0.5913000106811523,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.17239999771118164,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T13239","display_name":"Phosphorus compounds and reactions","score":0.05380000174045563,"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/intramolecular-cyclization","display_name":"intramolecular cyclization","score":0.7910000085830688},{"id":"https://openalex.org/keywords/amide-coupling","display_name":"amide coupling","score":0.8629999756813049},{"id":"https://openalex.org/keywords/nitrilotriacetic-acid","display_name":"nitrilotriacetic acid","score":0.9890000224113464},{"id":"https://openalex.org/keywords/ortho-substituted-anilines","display_name":"ortho-substituted anilines","score":0.9309999942779541},{"id":"https://openalex.org/keywords/triphenyl-phosphite","display_name":"triphenyl phosphite","score":0.9419999718666077},{"id":"https://openalex.org/keywords/solid-state-structure","display_name":"solid-state structure","score":0.5609999895095825},{"id":"https://openalex.org/keywords/ligand-synthesis","display_name":"ligand synthesis","score":0.503000020980835}],"concepts":[{"id":"https://openalex.org/C2776201271","wikidata":"https://www.wikidata.org/wiki/Q409292","display_name":"Piperazine","level":2,"score":0.8867837190628052},{"id":"https://openalex.org/C2776730177","wikidata":"https://www.wikidata.org/wiki/Q421721","display_name":"Acetamide","level":2,"score":0.8795515894889832},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7665584087371826},{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.7029665112495422},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.6343438029289246},{"id":"https://openalex.org/C2778306172","wikidata":"https://www.wikidata.org/wiki/Q425340","display_name":"Nitrilotriacetic acid","level":3,"score":0.5335486531257629},{"id":"https://openalex.org/C2778327999","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Carboxamide","level":2,"score":0.5124900341033936},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.48699504137039185},{"id":"https://openalex.org/C48424934","wikidata":"https://www.wikidata.org/wiki/Q898912","display_name":"Coupling reaction","level":3,"score":0.4737183451652527},{"id":"https://openalex.org/C116569031","wikidata":"https://www.wikidata.org/wiki/Q899107","display_name":"Ligand (biochemistry)","level":3,"score":0.462492972612381},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.4383174479007721},{"id":"https://openalex.org/C2779244968","wikidata":"https://www.wikidata.org/wiki/Q186414","display_name":"Aniline","level":2,"score":0.4118972420692444},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3903723657131195},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.21554160118103027},{"id":"https://openalex.org/C197404232","wikidata":"https://www.wikidata.org/wiki/Q319827","display_name":"Chelation","level":2,"score":0.08054518699645996},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.06723254919052124},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.04639744758605957},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.0},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1002/slct.202102576","doi":"https://doi.org/10.1002/slct.202102576","is_oa":true,"landing_page_url":"https://doi.org/10.1002/slct.202102576","pdf_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202102576","source":{"id":"https://openalex.org/S4210221416","display_name":"ChemistrySelect","issn_l":"2365-6549","issn":["2365-6549"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-1","ki-jl-1","norway-1","poland-40","russia-white-list-2","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"ChemistrySelect","raw_type":"journal-article"}],"best_oa_location":{"id":"doi:10.1002/slct.202102576","doi":"https://doi.org/10.1002/slct.202102576","is_oa":true,"landing_page_url":"https://doi.org/10.1002/slct.202102576","pdf_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202102576","source":{"id":"https://openalex.org/S4210221416","display_name":"ChemistrySelect","issn_l":"2365-6549","issn":["2365-6549"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","jufo-1","ki-jl-1","norway-1","poland-40","russia-white-list-2","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"ChemistrySelect","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G137528073","display_name":null,"funder_award_id":"SFI/15/RS-URF/3307","funder_id":"https://openalex.org/F4320320847","funder_display_name":"Science Foundation Ireland"},{"id":"https://openalex.org/G2290212825","display_name":null,"funder_award_id":"ERC-2015-STG-678202","funder_id":"https://openalex.org/F4320334678","funder_display_name":"European Research Council"}],"funders":[{"id":"https://openalex.org/F4320320847","display_name":"Science Foundation Ireland","ror":"https://ror.org/0271asj38"},{"id":"https://openalex.org/F4320334678","display_name":"European Research Council","ror":"https://ror.org/0472cxd90"}],"has_content":{"pdf":true,"grobid_xml":false},"content_urls":{"pdf":"https://content.openalex.org/works/W3203837618.pdf"},"referenced_works_count":44,"referenced_works":["https://openalex.org/W15668222","https://openalex.org/W278393088","https://openalex.org/W1938135664","https://openalex.org/W1967161172","https://openalex.org/W1970775906","https://openalex.org/W1975010993","https://openalex.org/W1975391649","https://openalex.org/W1979655323","https://openalex.org/W1982307016","https://openalex.org/W1985835523","https://openalex.org/W1994904386","https://openalex.org/W1997393650","https://openalex.org/W1999582957","https://openalex.org/W2006707401","https://openalex.org/W2010835181","https://openalex.org/W2021287759","https://openalex.org/W2023650882","https://openalex.org/W2041362370","https://openalex.org/W2048584409","https://openalex.org/W2052352527","https://openalex.org/W2053396558","https://openalex.org/W2063012302","https://openalex.org/W2064915707","https://openalex.org/W2066311520","https://openalex.org/W2082174525","https://openalex.org/W2082345487","https://openalex.org/W2086135051","https://openalex.org/W2122290971","https://openalex.org/W2142660635","https://openalex.org/W2151130802","https://openalex.org/W2164969314","https://openalex.org/W2314123842","https://openalex.org/W2319902168","https://openalex.org/W2333408874","https://openalex.org/W2588539969","https://openalex.org/W2807676901","https://openalex.org/W2925840629","https://openalex.org/W2949759696","https://openalex.org/W2950576909","https://openalex.org/W3020848186","https://openalex.org/W3029778732","https://openalex.org/W3039399752","https://openalex.org/W4246108227","https://openalex.org/W4253425712"],"related_works":["https://openalex.org/W2037578170","https://openalex.org/W2050026223","https://openalex.org/W2952872961","https://openalex.org/W2266278329","https://openalex.org/W2071866384","https://openalex.org/W2153089401","https://openalex.org/W2952516298","https://openalex.org/W2046890942","https://openalex.org/W2590279667","https://openalex.org/W3157429221"],"abstract_inverted_index":{"Abstract":[0],"The":[1,45],"synthesis":[2],"of":[3,23,69,112,122,131,137],"tripodal":[4,25,64,132],"carboxamide":[5,133],"ligands":[6,26],"using":[7,27,53,96],"one\u2010pot":[8],"phosphite":[9],"coupling":[10,57,72],"reactions":[11],"with":[12],"nitrilotriacetic":[13],"acid":[14],"(NTA)":[15],"and":[16,49,82,102,114],"4\u2010substituted":[17],"anilines":[18,30],"is":[19],"well":[20],"established.":[21],"Generation":[22],"such":[24],"ortho":[28,120],"\u2010substituted":[29],"(":[31,75,79,84],"2,6\u2212R":[32,50],"ArNH":[33,51],"2":[34,52,80,113],",":[35],"R=F,":[36],"Me,":[37],"i":[38],"Pr)":[39],"has":[40],"proven":[41],"to":[42],"be":[43],"challenging.":[44],"reaction":[46],"between":[47],"NTA":[48],"triphenylphosphite":[54],"as":[55],"a":[56],"reagent":[58],"did":[59],"not":[60],"yield":[61],"the":[62,67,119,129,138],"desired":[63,139],"carboxamide.":[65],"Rather,":[66],"formation":[68,130],"3,5\u2010dioxo\u20101\u2010piperazine":[70],"intramolecular":[71,126],"products":[73],"N\u2010(2,6\u2010difluorophenyl)\u20103,5\u2010dioxo\u20101\u2010piperazine\u2010N\u2010(2,6\u2010difluorophenyl)acetamide":[74],"1":[76],"),":[77],"N\u2010(2,6\u2010dimethyphenyl)\u20103,5\u2010dioxo\u20101\u2010piperazine\u2010N\u2010(2,6\u2010dimethylphenyl)acetamide":[78],")":[81,86],"N\u2010(2,6\u2010diisopropylphenyl)\u20103,5\u2010dioxo\u20101\u2010piperazine\u2010N\u2010(2,6\u2010diisopropylphenyl)acetamide":[83],"3":[85,115],"was":[87],"observed.":[88],"All":[89],"three":[90],"compounds":[91],"have":[92],"been":[93],"extensively":[94],"characterized":[95],"nuclear":[97],"magnetic":[98],"resonance,":[99],"Fourier\u2010transform":[100],"infra\u2010red":[101],"mass":[103],"spectrometry.":[104],"X\u2010ray":[105],"diffraction":[106],"analysis":[107],"yielded":[108],"solid":[109],"state":[110],"structures":[111],".":[116],"Substituents":[117],"at":[118],"position":[121],"aniline":[123],"thus":[124],"favours":[125],"cyclization":[127],"over":[128],"ligands,":[134],"preventing":[135],"preparation":[136],"bulky":[140],"ligand.":[141]},"counts_by_year":[{"year":2024,"cited_by_count":1}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2021-10-11T00:00:00"}