{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:41:49Z","timestamp":1786977709175,"version":"build-2736575974"},"reference-count":18,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2021,8,23]],"date-time":"2021-08-23T00:00:00Z","timestamp":1629676800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["N-1900 20190330"],"award-info":[{"award-number":["N-1900 20190330"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2021,8,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In this article, we describe simple one\u2010pot syntheses of 2H\u20101,3\u2010benzoxazines from ketones utilizing an imino\u2010pyridine directing group (R\n                    <jats:sup>1<\/jats:sup>\n                    R\n                    <jats:sup>2<\/jats:sup>\n                    \u2010C=N\u2212CH\n                    <jats:sub>2<\/jats:sub>\n                    \u2010Pyr), which promotes a Cu\u2010directed sp\n                    <jats:sup>2<\/jats:sup>\n                    hydroxylation using H\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    as oxidant and followed by an oxidative intramolecular C\u2212O bond formation upon addition of NEt\n                    <jats:sub>3<\/jats:sub>\n                    . This synthetic protocol is utilized in the gram scale synthesis of the 2H\u20101,3\u2010benzoxazine derived from benzophenone. Mechanistic studies reveal that the cyclization occurs via deprotonation of the benzylic position of the directing group to produce a 2\u2010azallyl anion intermediate, which is oxidized to the corresponding 2\u2010azaallyl radical before the C\u2212O bond formation event. Understanding of the cyclization mechanism also allowed us to develop reaction conditions that utilize catalytic amounts of Cu.\n                  <\/jats:p>","DOI":"10.1002\/ejoc.202100783","type":"journal-article","created":{"date-parts":[[2021,8,18]],"date-time":"2021-08-18T02:01:49Z","timestamp":1629252109000},"page":"4536-4540","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Practical One\u2010Pot Multistep Synthesis of 2H\u20101,3\u2010Benzoxazines Using Copper, Hydrogen Peroxide, and Triethylamine"],"prefix":"10.1002","volume":"2021","author":[{"given":"Rachel","family":"Trammell","sequence":"first","affiliation":[{"name":"Department of Chemistry Southern Methodist University  Dallas Texas 75275 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra","family":"Cordova","sequence":"additional","affiliation":[{"name":"Department of Chemistry Southern Methodist University  Dallas Texas 75275 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuming","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Southern Methodist University  Dallas Texas 75275 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sunipa","family":"Goswami","sequence":"additional","affiliation":[{"name":"Department of Chemistry Southern Methodist University  Dallas Texas 75275 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richel","family":"Murata","sequence":"additional","affiliation":[{"name":"Department of Chemistry Southern Methodist University  Dallas Texas 75275 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maxime A.","family":"Siegler","sequence":"additional","affiliation":[{"name":"Department of Chemistry The Johns Hopkins University  Baltimore Maryland 21218 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isaac","family":"Garcia\u2010Bosch","sequence":"additional","affiliation":[{"name":"Department of Chemistry Southern Methodist University  Dallas Texas 75275 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,8,23]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/np9903494"},{"key":"e_1_2_2_2_1","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.7b00209"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05934"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00368"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b01069"},{"key":"e_1_2_2_7_1","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","author":"Chen X.","year":"2020","journal-title":"Org. 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These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_2_15_1","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00349"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB00409C"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00233a031"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.202100783","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ejoc.202100783","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.202100783","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T15:29:26Z","timestamp":1760542166000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.202100783"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,8,23]]},"references-count":18,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2021,8,26]]}},"alternative-id":["10.1002\/ejoc.202100783"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.202100783","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,8,23]]},"assertion":[{"value":"2021-07-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-08-23","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}