{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T18:36:47Z","timestamp":1786991807688,"version":"build-2736575974"},"reference-count":54,"publisher":"Wiley","issue":"65","license":[{"start":{"date-parts":[[2024,11,5]],"date-time":"2024-11-05T00:00:00Z","timestamp":1730764800000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"},{"start":{"date-parts":[[2024,11,5]],"date-time":"2024-11-05T00:00:00Z","timestamp":1730764800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE-2055055"],"award-info":[{"award-number":["CHE-2055055"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2024,11,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We describe novel amine\u2010mediated transformation of alkynyl ketones and amides to generate 2\u2010methylene\u20102<jats:italic>H<\/jats:italic>\u2010pyrans, substituted 3\u2010hydroxy\u20109<jats:italic>H<\/jats:italic>\u2010fluoren\u20109\u2010ones, and amine\u2010incorporated arenes. These cascade processes are initiated by conjugate addition of secondary amine followed by hydrolysis of the enamine\/vinylogous amide intermediates. The product distribution is highly sensitive to the steric and electronic effects of the substituents on both the alkyne moieties, the tether structure connecting them, and the nature of the amine. Alkynyl amide participates in the Alder\u2010ene reaction favorably to generate more reactive allene amide that reacts with amine to generate amine\u2010incorporated arene products. These metal\u2010free cascade reactions are a useful synthetic method that can be exploited for the construction of various hetero\u2010 and carbocyclic systems.<\/jats:p>","DOI":"10.1002\/chem.202403270","type":"journal-article","created":{"date-parts":[[2024,9,22]],"date-time":"2024-09-22T21:59:33Z","timestamp":1727042373000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Cascade Reactions of Alkynyl Ketones and Amides to Generate Unsaturated Oxacycles and Aromatic Carbocycles"],"prefix":"10.1002","volume":"30","author":[{"given":"Kumudi J. W.","family":"Rajapaksa","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Illinois at Chicago  845\u2005W. Taylor St. Chicago, Illinois 60607 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hang","family":"Yan Wong","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Illinois at Chicago  845\u2005W. Taylor St. Chicago, Illinois 60607 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3958-5475","authenticated-orcid":false,"given":"Daesung","family":"Lee","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Illinois at Chicago  845\u2005W. Taylor St. Chicago, Illinois 60607 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,5]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1053829"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja106901u"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/b509540a"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob05254c"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo202424n"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)80108-2"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol062353u"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058418q"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4005905"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201412468"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03696"},{"key":"e_1_2_8_13_1","volume":"26","author":"Vo D.-V.","year":"2024","journal-title":"Org. Lett."},{"key":"e_1_2_8_14_1","unstructured":"\u00a0"},{"key":"e_1_2_8_15_2","doi-asserted-by":"crossref","unstructured":"C.\u2005L. Oepstad H.-R. Sliwka V. Partali Eur. J. Org. Chem.2010 3 435\u2013439;","DOI":"10.1002\/ejoc.200901093"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c02711"},{"key":"e_1_2_8_17_1","unstructured":"Reviews of the recent advances in oxa-6\u03c0 electrocyclization:"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.3390\/org2040021"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0406110"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1590870"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.11.092"},{"key":"e_1_2_8_22_1","unstructured":"1 4- and 1 6-addition of amines to acetylenic ketones:"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01243a002"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.17.2126"},{"key":"e_1_2_8_25_2","unstructured":"R. Mestres J. Chem. Soc. Perkin Trans.11972 10 805\u2013809;"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/poc.610031002"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397910801914343"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c02914"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.4c01071"},{"key":"e_1_2_8_30_1","unstructured":"The 2-methylene-2H-pyran core is a structural component in many natural products and bioactive molecules:"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.28.226"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/np300327y"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.funbio.2013.12.003"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/np9004213"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2016.01.002"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02251992"},{"key":"e_1_2_8_37_1","unstructured":"\u00a0"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19891220413"},{"key":"e_1_2_8_39_2","unstructured":"V.\u2005J. Ram P. Srivastava N. Agarwal A. Sharon P.\u2005R. Maulik J. Chem. Soc. Perkin Trans. 12001 16 1953\u20131959;"},{"key":"e_1_2_8_40_2","doi-asserted-by":"crossref","unstructured":"L. Millan M. Fuentealba C. Manzur D. Carrillo N. Faux B. Caro F. Robin-Le\u2005Guen S. Sinbandhit I. Ledoux-Rak J.-R. Hamon Eur. J. Inorg. Chem.2006 6 1131\u20131138;","DOI":"10.1002\/ejic.200500955"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo062170l"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob41962b"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.01.094"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02380"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201801303"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/D4OB00835A"},{"key":"e_1_2_8_47_1","unstructured":"In the reaction with an ester-tethered triyne A1 amines could not be used as a nucleophile to generate amine-incorporated arene products because the ester bond cleavage occurred before an Alder-ene reaction See an example in Ref 3."},{"key":"e_1_2_8_48_1","unstructured":"The structure of IN-1a formed from piperidine was fully characterized See Supporting Information."},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.04.100"},{"key":"e_1_2_8_50_1","unstructured":"The reaction of1awith acetic acid and DABCO (20 mol%) to form2awas monitored by NMR in toluene-d6 See Supporting Information for the stack-plot of these NMRs ."},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198407271"},{"key":"e_1_2_8_52_1","unstructured":"\u00a0"},{"key":"e_1_2_8_53_2","first-page":"819","volume":"2","author":"Chodkiewicz W.","year":"1957","journal-title":"Ann. Chim. (Paris)"},{"key":"e_1_2_8_54_2","unstructured":"P. Cadiot W. Chodkiewicz Chemistry of Acetylenes (Ed: H.\u2005G. Viehe) Marcel Dekker New York1969 597."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202403270","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202403270","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T21:16:48Z","timestamp":1760303808000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202403270"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,5]]},"references-count":54,"journal-issue":{"issue":"65","published-print":{"date-parts":[[2024,11,21]]}},"alternative-id":["10.1002\/chem.202403270"],"URL":"https:\/\/doi.org\/10.1002\/chem.202403270","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,5]]},"assertion":[{"value":"2024-08-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-05","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202403270"}}