{"id":"https://openalex.org/W4247054615","doi":"https://doi.org/10.1002/9781118695692.ch13","title":"Smith Indole Synthesis","display_name":"Smith Indole Synthesis","publication_year":2016,"publication_date":"2016-06-17","ids":{"openalex":"https://openalex.org/W4247054615","doi":"https://doi.org/10.1002/9781118695692.ch13"},"language":"en","primary_location":{"id":"doi:10.1002/9781118695692.ch13","doi":"https://doi.org/10.1002/9781118695692.ch13","is_oa":false,"landing_page_url":"https://doi.org/10.1002/9781118695692.ch13","pdf_url":null,"source":{"id":"https://openalex.org/S4306464293","display_name":"Wiley eBooks","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"ebook platform"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Indole Ring Synthesis","raw_type":"other"},"volume":{"id":"https://openalex.org/W4248040139","display_name":"Indole Ring Synthesis"},"type":"other","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":[{"id":"https://openalex.org/I107672454","display_name":"Dartmouth College","ror":"https://ror.org/049s0rh22","country_code":"US","type":"education","lineage":["https://openalex.org/I107672454"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Gordon W. Gribble","raw_affiliation_strings":["Department of Chemistry, Dartmouth College, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Dartmouth College, USA","institution_ids":["https://openalex.org/I107672454"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5049245360"],"corresponding_institution_ids":["https://openalex.org/I107672454"],"apc_list":null,"apc_paid":null,"fwci":null,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":null,"cited_by_percentile_year":null,"biblio":{"volume":null,"issue":null,"first_page":"181","last_page":"185"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12973","display_name":"Synthesis of Indole Derivatives","score":0.9721999764442444,"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":0.9721999764442444,"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":0.006500000134110451,"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":0.006399999838322401,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/indole-synthesis","display_name":"indole synthesis","score":0.9210000038146973},{"id":"https://openalex.org/keywords/carboxylic-esters","display_name":"carboxylic acid esters","score":0.9629999995231628},{"id":"https://openalex.org/keywords/2-substituted-indoles","display_name":"2-substituted indoles","score":0.9390000104904175},{"id":"https://openalex.org/keywords/2-3-disubstituted-indoles","display_name":"2,3-disubstituted indoles","score":0.9570000171661377},{"id":"https://openalex.org/keywords/bisindoles","display_name":"bisindoles","score":0.8309999704360962},{"id":"https://openalex.org/keywords/acid-catalyzed-cyclization","display_name":"acid-catalyzed cyclization","score":0.9179999828338623},{"id":"https://openalex.org/keywords/tmeda","display_name":"TMEDA","score":0.8619999885559082}],"concepts":[{"id":"https://openalex.org/C192527728","wikidata":"https://www.wikidata.org/wiki/Q1465700","display_name":"Indole test","level":2,"score":0.9591305255889893},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7012397646903992},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.5652021765708923},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.5199674367904663},{"id":"https://openalex.org/C2776734949","wikidata":"https://www.wikidata.org/wiki/Q408452","display_name":"Indole alkaloid","level":3,"score":0.5013093948364258},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4480460584163666},{"id":"https://openalex.org/C111771559","wikidata":"https://www.wikidata.org/wiki/Q66295","display_name":"Derivative (finance)","level":2,"score":0.43306994438171387},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3706570863723755},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.04108145833015442},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0},{"id":"https://openalex.org/C106159729","wikidata":"https://www.wikidata.org/wiki/Q2294553","display_name":"Financial economics","level":1,"score":0.0},{"id":"https://openalex.org/C162324750","wikidata":"https://www.wikidata.org/wiki/Q8134","display_name":"Economics","level":0,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1002/9781118695692.ch13","doi":"https://doi.org/10.1002/9781118695692.ch13","is_oa":false,"landing_page_url":"https://doi.org/10.1002/9781118695692.ch13","pdf_url":null,"source":{"id":"https://openalex.org/S4306464293","display_name":"Wiley eBooks","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"ebook platform"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Indole Ring Synthesis","raw_type":"other"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":16,"referenced_works":["https://openalex.org/W1481933915","https://openalex.org/W1968667947","https://openalex.org/W1988277172","https://openalex.org/W1988705437","https://openalex.org/W1994505359","https://openalex.org/W2014513465","https://openalex.org/W2015515109","https://openalex.org/W2022189912","https://openalex.org/W2026443712","https://openalex.org/W2031268048","https://openalex.org/W2033682553","https://openalex.org/W2042139140","https://openalex.org/W2056591141","https://openalex.org/W2175192969","https://openalex.org/W2180922517","https://openalex.org/W2949952473"],"related_works":["https://openalex.org/W1985620892","https://openalex.org/W7034232293","https://openalex.org/W2949604976","https://openalex.org/W1561203182","https://openalex.org/W2085760827","https://openalex.org/W1969085281","https://openalex.org/W1968667947","https://openalex.org/W2055106362","https://openalex.org/W2952491906","https://openalex.org/W2913213926"],"abstract_inverted_index":{"Somewhat":[0],"related":[1,43],"to":[2,30,44,81,120],"the":[3,10,19,37,59,97,147],"Madelung":[4],"and":[5,15,33,63,75,89,91,106],"Wender":[6],"indole":[7,42,47,61,103,140],"syntheses":[8,82],"is":[9,69],"method":[11],"developed":[12],"by":[13],"Smith":[14,60,102],"Visnick,":[16],"which":[17,116],"features":[18],"dilithio":[20],"species":[21],"from":[22],"ortho-alkyl-N-tri-methylsilyl":[23],"anilines":[24],"reacting":[25],"with":[26],"carboxylic":[27],"acid":[28],"esters":[29],"give":[31],"2-substituted":[32],"2,3-disubstituted":[34],"indoles.":[35],"For":[36],"synthesis":[38,112],"of":[39,58,66,83,96,113,146],"a":[40,64,94,101,109],"model":[41],"penitrem":[45],"D,":[46],"was":[48,118,141],"an":[49],"advanced":[50],"intermediate.":[51],"Several":[52],"other":[53],"groups":[54],"have":[55],"made":[56],"use":[57],"synthesis,":[62],"summary":[65],"this":[67,72,131],"work":[68],"shown":[70],"in":[71,115,127],"chapter.":[73],"Gribble":[74],"coworkers":[76],"prepared":[77,126],"2-(2-pyridinyl)indoles":[78],"en":[79],"route":[80],"several":[84],"zwitterionic":[85],"indolo[2,3-a]":[86],"quinolizine":[87],"alkaloids,":[88],"Husson":[90],"Hashimoto":[92],"synthesized":[93,142],"derivative":[95],"alkaloid":[98],"goniomitine":[99],"via":[100],"synthesis.":[104],"Henegar":[105],"Hunt":[107],"reported":[108],"very":[110],"convenient":[111],"2-trifluoromethylindole,":[114],"TMEDA":[117],"found":[119],"be":[121],"necessary.":[122],"Two":[123],"bis-indoles":[124],"were":[125],"low":[128],"yield,":[129],"but":[130],"approach":[132],"failed":[133],"for":[134],"n":[135],"=":[136],"1.":[137],"The":[138],"bridged":[139],"following":[143],"acid-catalyzed":[144],"cyclization":[145],"initially":[148],"formed":[149],"indole.":[150]},"counts_by_year":[],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2022-05-12T00:00:00"}