{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T08:33:36Z","timestamp":1788510816700,"version":"build-2803163510"},"reference-count":63,"publisher":"American Chemical Society (ACS)","issue":"16","license":[{"start":{"date-parts":[[2024,8,1]],"date-time":"2024-08-01T00:00:00Z","timestamp":1722470400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2024,8,1]],"date-time":"2024-08-01T00:00:00Z","timestamp":1722470400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2024,8,1]],"date-time":"2024-08-01T00:00:00Z","timestamp":1722470400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["23-73-00014"],"award-info":[{"award-number":["23-73-00014"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2024,8,16]]},"DOI":"10.1021\/acs.joc.4c00726","type":"journal-article","created":{"date-parts":[[2024,8,1]],"date-time":"2024-08-01T14:56:56Z","timestamp":1722524216000},"page":"11183-11194","source":"Crossref","is-referenced-by-count":7,"title":["Sequential Modification of Pyrrole Ring with up to Three Different Nucleophiles"],"prefix":"10.1021","volume":"89","author":[{"given":"Victoria E.","family":"Shambalova","sequence":"first","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roman V.","family":"Larkovich","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3653-1439","authenticated-orcid":true,"given":"Alexander S.","family":"Aldoshin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantin A.","family":"Lyssenko","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8941-4856","authenticated-orcid":true,"given":"Mikhail S.","family":"Nechaev","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation"},{"name":"A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninsky Prospect 29, Moscow 119991, Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9162-5169","authenticated-orcid":true,"given":"Valentine G.","family":"Nenajdenko","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2024,8,1]]},"reference":[{"key":"ref1\/cit1a","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs15333e"},{"key":"ref1\/cit1b","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00418B"},{"key":"ref1\/cit1c","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00468"},{"key":"ref1\/cit1d","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202200082"},{"key":"ref1\/cit1e","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610741"},{"key":"ref1\/cit1f","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC06133J"},{"key":"ref1\/cit1g","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-990835"},{"key":"ref1\/cit1h","doi-asserted-by":"publisher","DOI":"10.1149\/2.F06024IF"},{"key":"ref2\/cit2a","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob40735g"},{"key":"ref2\/cit2b","doi-asserted-by":"publisher","DOI":"10.1007\/s41061-020-0287-7"},{"key":"ref2\/cit2c","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103014"},{"key":"ref2\/cit2d","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201802142"},{"key":"ref2\/cit2e","doi-asserted-by":"publisher","DOI":"10.1055\/s-0040-1706552"},{"key":"ref2\/cit2f","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09582H"},{"key":"ref2\/cit2g","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC05627K"},{"key":"ref2\/cit2h","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c02165"},{"key":"ref2\/cit2i","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c11092"},{"key":"ref2\/cit2j","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b01091"},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1002\/9780470187326.ch3","volume-title":"Chemistry of Heterocyclic Compounds: A Series Of Monographs","volume":"48","author":"Jackson A. H.","year":"1990"},{"key":"ref4\/cit4a","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201703723"},{"key":"ref4\/cit4b","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201700221"},{"key":"ref4\/cit4c","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00041"},{"key":"ref5\/cit5a","first-page":"151","volume-title":"Adv. Heterocycl. Chem.","volume":"115","author":"Pelkey E. T.","year":"2015"},{"key":"ref5\/cit5b","first-page":"433","volume-title":"Adv. Heterocycl. Chem.","volume":"128","author":"Pelkey E. T.","year":"2019"},{"key":"ref5\/cit5c","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.4143"},{"key":"ref5\/cit5d","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201500659"},{"key":"ref6\/cit6a","doi-asserted-by":"publisher","DOI":"10.2174\/1570179414666170908165445"},{"key":"ref6\/cit6b","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(01)06890-8"},{"key":"ref6\/cit6c","doi-asserted-by":"publisher","DOI":"10.1007\/BF03258426"},{"key":"ref7\/cit7","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1611014"},{"key":"ref8\/cit8","series-title":"Progress in the Chemistry of Organic Natural Products","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-030-52966-6","volume-title":"Progress in the Chemistry of Organic Natural Products 112","volume":"112","author":"Kinghorn A. D.","year":"2020"},{"key":"ref9\/cit9a","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA09047K"},{"key":"ref9\/cit9b","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.02.069"},{"key":"ref9\/cit9c","doi-asserted-by":"publisher","DOI":"10.1021\/cr00038a009"},{"key":"ref9\/cit9d","doi-asserted-by":"publisher","DOI":"10.1155\/2010\/315056"},{"key":"ref9\/cit9e","first-page":"109","volume-title":"Studies in Natural Products Chemistry","volume":"28","author":"Ghisalberti E. L.","year":"2003"},{"key":"ref10\/cit10a","doi-asserted-by":"publisher","DOI":"10.13005\/ojc\/300101"},{"key":"ref10\/cit10b","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428021100201"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1070\/RCR4871"},{"key":"ref12\/cit12a","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.0c00830"},{"key":"ref12\/cit12b","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2020.109639"},{"key":"ref12\/cit12c","doi-asserted-by":"publisher","DOI":"10.1039\/B610213C"},{"key":"ref12\/cit12d","doi-asserted-by":"publisher","DOI":"10.1080\/14756360701425014"},{"key":"ref12\/cit12e","doi-asserted-by":"publisher","DOI":"10.2174\/1389557515666151016124957"},{"key":"ref12\/cit12f","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01788"},{"key":"ref12\/cit12g","volume-title":"Fluorine in Heterocyclic Chemistry Vol. 1:5-Membered Heterocycles and Macrocycles","author":"Nenajdenko V.","year":"2014"},{"key":"ref12\/cit12h","volume-title":"Fluorine in Heterocyclic Chemistry Vol. 2:6-Membered Heterocycles","author":"Nenajdenko V.","year":"2014"},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1007\/s10593-018-2298-7"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.1021\/jo9013436"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c01477"},{"key":"ref16\/cit16a","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2003.10.127"},{"key":"ref16\/cit16b","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402535"},{"key":"ref16\/cit16c","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2003.11.093"},{"key":"ref16\/cit16d","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500826"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00935"},{"key":"ref18\/cit18","unstructured":"Deposition\nnumbers CCDC 2321149\n(for B) and CCDC 2321150 (for 3h) contain\nthe supplementary crystallographic data for this paper. These data\nare provided free of charge by the joint Cambridge Crystallographic\nData Centre and Fachinformationszentrum Karlsruhe Access Structures\nservice."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","DOI":"10.1002\/352760393X","volume-title":"Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications","author":"Kirsch P.","year":"2004"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570340102"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302604"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1021\/jo101589h"},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97017-6"},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c02380"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1021\/ar1000956"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.4c00726","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.4c00726","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,8,16]],"date-time":"2024-08-16T08:37:00Z","timestamp":1723797420000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.4c00726"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,8,1]]},"references-count":63,"journal-issue":{"issue":"16","published-print":{"date-parts":[[2024,8,16]]}},"alternative-id":["10.1021\/acs.joc.4c00726"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.4c00726","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,8,1]]}}}