{"id":"https://openalex.org/W2050100357","doi":"https://doi.org/10.1021/ja01025a055","title":"Cyclization of tryptophan and tryptamine derivatives to pyrrolo[2,3-b]indoles","display_name":"Cyclization of tryptophan and tryptamine derivatives to pyrrolo[2,3-b]indoles","publication_year":1968,"publication_date":"1968-11-01","ids":{"openalex":"https://openalex.org/W2050100357","doi":"https://doi.org/10.1021/ja01025a055","mag":"2050100357","pmid":"https://pubmed.ncbi.nlm.nih.gov/5682451"},"language":"en","primary_location":{"id":"doi:10.1021/ja01025a055","doi":"https://doi.org/10.1021/ja01025a055","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja01025a055","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"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/A5111589437","display_name":"Motonori Ohno","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Motonori Ohno","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5003226300","display_name":"Thomas F. Spande","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Thomas F. Spande","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5005748301","display_name":"Bernhard Witkop","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Bernhard Witkop","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.4957,"has_fulltext":false,"cited_by_count":42,"citation_normalized_percentile":{"value":0.85894044,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":87,"max":96},"biblio":{"volume":"90","issue":"23","first_page":"6521","last_page":"6522"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12973","display_name":"Synthesis of Indole Derivatives","score":0.885699987411499,"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/T12973","display_name":"Synthesis of Indole Derivatives","score":0.885699987411499,"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/T13188","display_name":"Synthesis and bioactivity of alkaloids","score":0.04340000078082085,"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":0.008200000040233135,"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/tryptophan-derivatives","display_name":"tryptophan derivatives","score":0.8989999890327454},{"id":"https://openalex.org/keywords/tryptamine-derivatives","display_name":"tryptamine derivatives","score":0.9990000128746033},{"id":"https://openalex.org/keywords/pyrrolo-2-3-b-indole","display_name":"pyrrolo[2,3-b]indole","score":0.9660000205039978},{"id":"https://openalex.org/keywords/cyclization","display_name":"cyclization","score":0.7760000228881836},{"id":"https://openalex.org/keywords/indole-synthesis","display_name":"indole synthesis","score":0.6759999990463257},{"id":"https://openalex.org/keywords/heterocycle-synthesis","display_name":"heterocyclic synthesis","score":0.5040000081062317}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9854880571365356},{"id":"https://openalex.org/C2777135210","wikidata":"https://www.wikidata.org/wiki/Q409439","display_name":"Tryptamine","level":2,"score":0.9644594788551331},{"id":"https://openalex.org/C2776706248","wikidata":"https://www.wikidata.org/wiki/Q181003","display_name":"Tryptophan","level":3,"score":0.8214141726493835},{"id":"https://openalex.org/C192527728","wikidata":"https://www.wikidata.org/wiki/Q1465700","display_name":"Indole test","level":2,"score":0.5913577675819397},{"id":"https://openalex.org/C2909645108","wikidata":"https://www.wikidata.org/wiki/Q10705510","display_name":"Tryptamines","level":3,"score":0.5405724048614502},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5034899115562439},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3388798236846924},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.1874190866947174},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.0971381664276123}],"mesh":[{"descriptor_ui":"D002621","descriptor_name":"Chemistry","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007211","descriptor_name":"Indoles","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D011758","descriptor_name":"Pyrroles","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D014363","descriptor_name":"Tryptamines","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D014364","descriptor_name":"Tryptophan","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D055598","descriptor_name":"Chemical Phenomena","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ja01025a055","doi":"https://doi.org/10.1021/ja01025a055","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja01025a055","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:5682451","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/5682451","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":"Journal of the American Chemical Society","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2020594810","https://openalex.org/W2607285746","https://openalex.org/W2035111752","https://openalex.org/W2170650086","https://openalex.org/W2028139252","https://openalex.org/W2072147415","https://openalex.org/W2019977924","https://openalex.org/W2951045927","https://openalex.org/W2005029423","https://openalex.org/W2406930793"],"abstract_inverted_index":{"ADVERTISEMENT":[0],"RETURN":[1],"TO":[2],"ISSUEPREVArticleNEXTCyclization":[3],"of":[4,52,87,113],"tryptophan":[5],"and":[6,15,62,67,96,140,157,173,175],"tryptamine":[7],"derivatives":[8],"to":[9,74,79],"pyrrolo[2,3-b]indolesMotonori":[10],"Ohno,":[11],"Thomas":[12],"F.":[13],"Spande,":[14],"Bernhard":[16],"WitkopCite":[17],"this:":[18],"J.":[19],"Am.":[20],"Chem.":[21],"Soc.":[22],"1968,":[23],"90,":[24],"23,":[25],"6521\u20136522Publication":[26],"Date":[27],"(Print):November":[28],"1,":[29],"1968Publication":[30],"History":[31],"Published":[32],"online1":[33],"May":[34],"2002Published":[35],"inissue":[36],"1":[37],"November":[38,58],"1968https://pubs.acs.org/doi/10.1021/ja01025a055https://doi.org/10.1021/ja01025a055research-articleACS":[39],"PublicationsRequest":[40],"reuse":[41],"permissionsArticle":[42],"Views679Altmetric-Citations37LEARN":[43],"ABOUT":[44],"THESE":[45],"METRICSArticle":[46],"Views":[47],"are":[48,71,84],"the":[49,80,85,114,125,138,141,146,153,159],"COUNTER-compliant":[50],"sum":[51],"full":[53],"text":[54],"article":[55,119],"downloads":[56],"since":[57],"2008":[59],"(both":[60],"PDF":[61],"HTML)":[63],"across":[64],"all":[65],"institutions":[66],"individuals.":[68],"These":[69],"metrics":[70],"regularly":[72],"updated":[73,97],"reflect":[75],"usage":[76],"leading":[77],"up":[78],"last":[81],"few":[82],"days.Citations":[83],"number":[86],"other":[88],"articles":[89],"citing":[90],"this":[91],"article,":[92],"calculated":[93],"by":[94],"Crossref":[95,103],"daily.":[98],"Find":[99,149],"more":[100,150],"information":[101,151],"about":[102,137],"citation":[104],"counts.The":[105],"Altmetric":[106,154],"Attention":[107,155],"Score":[108,156],"is":[109,161],"a":[110,117,130],"quantitative":[111],"measure":[112],"attention":[115],"that":[116],"research":[118],"has":[120],"received":[121],"online.":[122],"Clicking":[123],"on":[124,152],"donut":[126],"icon":[127],"will":[128],"load":[129],"page":[131],"at":[132],"altmetric.com":[133],"with":[134,169],"additional":[135],"details":[136],"score":[139,160],"social":[142],"media":[143],"presence":[144],"for":[145],"given":[147],"article.":[148],"how":[158],"calculated.":[162],"Share":[163,178],"Add":[164],"toView":[165],"InAdd":[166],"Full":[167],"Text":[168],"ReferenceAdd":[170],"Description":[171],"ExportRISCitationCitation":[172],"abstractCitation":[174],"referencesMore":[176],"Options":[177],"onFacebookTwitterWechatLinked":[179],"InRedditEmail":[180],"Other":[181],"access":[182],"optionsGet":[183],"e-Alertsclose":[184],"Get":[185],"e-Alerts":[186]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2016,"cited_by_count":2},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}