{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,27]],"date-time":"2026-01-27T12:15:32Z","timestamp":1769516132564,"version":"3.49.0"},"reference-count":73,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2017,12,4]],"date-time":"2017-12-04T00:00:00Z","timestamp":1512345600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"FCT - Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["UID\/QUI\/00100\/2013"],"award-info":[{"award-number":["UID\/QUI\/00100\/2013"]}]},{"name":"FCT - Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["PTDC\/BBB-EBB\/0122\/2014"],"award-info":[{"award-number":["PTDC\/BBB-EBB\/0122\/2014"]}]},{"name":"FCT - Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["RECI\/QEQ-QIN\/0189\/2012"],"award-info":[{"award-number":["RECI\/QEQ-QIN\/0189\/2012"]}]},{"name":"FCT - Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["022125"],"award-info":[{"award-number":["022125"]}]},{"name":"Research Unit GREEN-it \u201cBioresources for Sustainability\u201d","award":["UID\/Multi\/04551\/2013"],"award-info":[{"award-number":["UID\/Multi\/04551\/2013"]}]},{"name":"IST-UL NMR Network"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Adv Synth Catal"],"published-print":{"date-parts":[[2018,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>An efficient and sustainable one\u2010step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available <jats:italic>ortho<\/jats:italic>\u2010substituted diamines and <jats:italic>ortho<\/jats:italic>\u2010substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA\u2010laccase\u2010catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including <jats:italic>N<\/jats:italic>\u2010substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions.<\/jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/png\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/adsc201701228-toc-0001-m.png\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text>\n<\/jats:p>","DOI":"10.1002\/adsc.201701228","type":"journal-article","created":{"date-parts":[[2017,11,13]],"date-time":"2017-11-13T21:58:43Z","timestamp":1510610323000},"page":"575-583","source":"Crossref","is-referenced-by-count":30,"title":["A Sustainable Synthesis of Asymmetric Phenazines and Phenoxazinones Mediated by CotA\u2010Laccase"],"prefix":"10.1002","volume":"360","author":[{"given":"Ana Catarina","family":"Sousa","sequence":"first","affiliation":[{"name":"\u00c1rea Departamental de Engenharia Qu\u00edmica, ISEL \u2013 Instituto Superior de Engenharia de Lisboa Instituto Polit\u00e9cnico de Lisboa  R. Conselheiro Em\u00eddio Navarro, 1 1959-007 Lisboa Portugal"},{"name":"Centro de Qu\u00edmica Estrutural, Complexo I; Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1049-001 Lisboa Portugal"}]},{"given":"M.","family":"Concei\u00e7\u00e3o\u2005Oliveira","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Complexo I; Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1049-001 Lisboa Portugal"}]},{"given":"L\u00edgia O.","family":"Martins","sequence":"additional","affiliation":[{"name":"Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica Ant\u00f3nio Xavier Universidade Nova de Lisboa  Av da Rep\u00fablica 2780-157 Oeiras Portugal"}]},{"given":"M. Paula","family":"Robalo","sequence":"additional","affiliation":[{"name":"\u00c1rea Departamental de Engenharia Qu\u00edmica, ISEL \u2013 Instituto Superior de Engenharia de Lisboa Instituto Polit\u00e9cnico de Lisboa  R. Conselheiro Em\u00eddio Navarro, 1 1959-007 Lisboa Portugal"},{"name":"Centro de Qu\u00edmica Estrutural, Complexo I; Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1049-001 Lisboa Portugal"}]}],"member":"311","published-online":{"date-parts":[[2017,12,4]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(96)02190-9"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.31.5.789"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob40325d"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.phyto.44.013106.145710"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.09.032"},{"key":"e_1_2_6_7_1","doi-asserted-by":"crossref","first-page":"290","DOI":"10.1093\/jac\/dkr444","volume":"2","author":"Cholo M. C.","year":"2012","journal-title":"J. Antimicrob. Chemoth."},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1080\/00032711003653791"},{"key":"e_1_2_6_9_1","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","first-page":"55","author":"Data P.","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC04863C"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/b111655j"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/B917601B"},{"key":"e_1_2_6_14_1","unstructured":"\u00a0"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm020913z"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm020918w"},{"key":"e_1_2_6_17_1","unstructured":"\u00a0"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200901206"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/np100344u"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/B401147C"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-010-2509-3"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr020473j"},{"key":"e_1_2_6_23_1","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2006.06.013"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397910701316136"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja406131a"},{"key":"e_1_2_6_27_1","first-page":"495","volume":"25","author":"Kour H.","year":"2014","journal-title":"SYNLETT"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2017.01.002"},{"key":"e_1_2_6_29_1","first-page":"705","author":"Yu L.","year":"2012","journal-title":"J. Organomet. Chem."},{"key":"e_1_2_6_30_1","first-page":"365","volume":"2","author":"Choudhary A. S.","year":"2014","journal-title":"Can. Chem. Trans."},{"key":"e_1_2_6_31_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-016-7987-5"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201300960"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800775"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-009-1869-z"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1186\/1475-2859-7-32"},{"key":"e_1_2_6_37_1","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo048454s"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcatb.2006.12.006"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(02)00872-4"},{"key":"e_1_2_6_41_1","unstructured":"\u00a0"},{"key":"e_1_2_6_42_2","first-page":"3126","author":"Leutbecher H.","year":"2005","journal-title":"Synlett"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201200413"},{"key":"e_1_2_6_44_2","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1002\/ardp.201200413","volume":"346","author":"Leutbecher H.","year":"2013","journal-title":"Arch. Pharm. Chem. Life Sci."},{"key":"e_1_2_6_44_3","doi-asserted-by":"crossref","first-page":"676","DOI":"10.1039\/b822977e","volume":"11","author":"Neumann","year":"2009","journal-title":"Green Chem."},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800791"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201200051"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo202082v"},{"key":"e_1_2_6_48_1","unstructured":"\u00a0"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201300501"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC00901K"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC02511C"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6GC02050J"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.3390\/M730"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/b920081a"},{"key":"e_1_2_6_55_1","unstructured":"\u00a0"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0168-1656(99)00100-5"},{"key":"e_1_2_6_57_2","first-page":"70","author":"Bruyneel F.","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.nbt.2015.09.004"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcatb.2009.12.018"},{"key":"e_1_2_6_60_2","first-page":"10","author":"Bruyneel F.","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M301251200"},{"key":"e_1_2_6_62_1","unstructured":"\u00a0"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M505806200"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.68.10.4965-4970.2002"},{"key":"e_1_2_6_65_1","unstructured":"\u00a0"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1093\/oxfordjournals.jbchem.a123669"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/0304-4165(92)90029-T"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00441a026"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M505806200"},{"key":"e_1_2_6_70_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M200827200"},{"key":"e_1_2_6_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/b504806k"},{"key":"e_1_2_6_72_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00775-007-0312-0"},{"key":"e_1_2_6_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(76)90527-3"}],"container-title":["Advanced Synthesis &amp; Catalysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fadsc.201701228","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/adsc.201701228","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T11:01:16Z","timestamp":1759748476000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/adsc.201701228"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,12,4]]},"references-count":73,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2018,2]]}},"alternative-id":["10.1002\/adsc.201701228"],"URL":"https:\/\/doi.org\/10.1002\/adsc.201701228","archive":["Portico"],"relation":{},"ISSN":["1615-4150","1615-4169"],"issn-type":[{"value":"1615-4150","type":"print"},{"value":"1615-4169","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,12,4]]}}}