{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T12:42:17Z","timestamp":1785415337953,"version":"3.56.0"},"reference-count":31,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2022,8,23]],"date-time":"2022-08-23T00:00:00Z","timestamp":1661212800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2022,8,23]],"date-time":"2022-08-23T00:00:00Z","timestamp":1661212800000},"content-version":"am","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2022,8,23]],"date-time":"2022-08-23T00:00:00Z","timestamp":1661212800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2022,8,5]]},"abstract":"<jats:p>\n                    The broad application of 1\n                    <jats:italic>H<\/jats:italic>\n                    -indazoles has prompted the development of several approaches for the synthesis of such compounds, including metal-free, palladium-, or copper-promoted intramolecular\n                    <jats:italic>N<\/jats:italic>\n                    -arylation of in situ-generated or isolated\n                    <jats:italic>o<\/jats:italic>\n                    -haloarylhydrazones. Such methods mainly start from\n                    <jats:italic>o<\/jats:italic>\n                    -bromo derivatives due to the better yield observed when compared to those obtained from\n                    <jats:italic>o<\/jats:italic>\n                    -chloroarylhydrazones. However, the\n                    <jats:italic>o<\/jats:italic>\n                    -chloroarylaldehydes and\n                    <jats:italic>o<\/jats:italic>\n                    -chloroarylketones used to prepare the arylhydrazones are more commercially available and less expensive than brominated analogs. Seeking to cover a lack in the literature, this work reports a convenient protocol for the synthesis of\n                    <jats:italic>N<\/jats:italic>\n                    -phenyl- and\n                    <jats:italic>N<\/jats:italic>\n                    -thiazolyl-1\n                    <jats:italic>H<\/jats:italic>\n                    -indazoles by copper-catalyzed intramolecular\n                    <jats:italic>N<\/jats:italic>\n                    -arylation of\n                    <jats:italic>o<\/jats:italic>\n                    -chlorinated arylhydrazones. Therefore, a series of seven\n                    <jats:italic>N<\/jats:italic>\n                    -phenyl derivatives and a series of six novel\n                    <jats:italic>N<\/jats:italic>\n                    -thiazolyl derivatives was obtained in 10\u201370% and 12\u201335% yield, respectively, after stirring the\n                    <jats:italic>o<\/jats:italic>\n                    -chlorinated arylhydrazones, CuI, KOH, and 1,10-phenantroline for 12\u201348 hours in DMF at 120 \u00b0C. The products were isolated by column chromatography on silica gel. All products were fully characterized by HRMS as well as\n                    <jats:sup>1<\/jats:sup>\n                    H and\n                    <jats:sup>13<\/jats:sup>\n                    C NMR spectroscopy. Thus, this approach is valuable for promoting the synthesis of\n                    <jats:italic>N<\/jats:italic>\n                    -phenyl-1\n                    <jats:italic>H<\/jats:italic>\n                    -indazoles in a higher yield than that reported in the literature using copper catalysis and the same substrates. This study also prompted the first reported synthesis of pharmacologically interesting\n                    <jats:italic>N<\/jats:italic>\n                    -thiazolyl derivatives.\n                  <\/jats:p>","DOI":"10.3762\/bjoc.18.110","type":"journal-article","created":{"date-parts":[[2022,8,23]],"date-time":"2022-08-23T04:17:02Z","timestamp":1661228222000},"page":"1079-1087","source":"Crossref","is-referenced-by-count":6,"title":["Synthesis of\n                    <i>N<\/i>\n                    -phenyl- and\n                    <i>N<\/i>\n                    -thiazolyl-1\n                    <i>H<\/i>\n                    -indazoles by copper-catalyzed intramolecular\n                    <i>N<\/i>\n                    -arylation of\n                    <i>ortho<\/i>\n                    -chlorinated arylhydrazones"],"prefix":"10.3762","volume":"18","author":[{"given":"Yara Cristina Marchioro","family":"Barbosa","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/0310smc09","id-type":"ROR","asserted-by":"publisher"},{"id":"https:\/\/www.isni.org\/0000000403882432","id-type":"ISNI","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guilherme Caneppele","family":"Paveglio","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/0310smc09","id-type":"ROR","asserted-by":"publisher"},{"id":"https:\/\/www.isni.org\/0000000403882432","id-type":"ISNI","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudio Martin Pereira","family":"de Pereira","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05msy9z54","id-type":"ROR","asserted-by":"publisher"},{"id":"https:\/\/www.isni.org\/0000000121346519","id-type":"ISNI","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sidnei","family":"Moura","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/05rpzs058","id-type":"ROR","asserted-by":"publisher"},{"id":"https:\/\/www.isni.org\/000000011481197X","id-type":"ISNI","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4444-846X","authenticated-orcid":false,"given":"Cristiane 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Antonio","family":"Casagrande","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/0310smc09","id-type":"ROR","asserted-by":"publisher"},{"id":"https:\/\/www.isni.org\/0000000403882432","id-type":"ISNI","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3950-0972","authenticated-orcid":false,"given":"Lucas","family":"Pizzuti","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/0310smc09","id-type":"ROR","asserted-by":"publisher"},{"id":"https:\/\/www.isni.org\/0000000403882432","id-type":"ISNI","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"2086","published-online":{"date-parts":[[2022,8,23]]},"reference":[{"key":"ref1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23112783"},{"key":"ref2","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201800253"},{"key":"ref3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.03.075"},{"key":"ref4","doi-asserted-by":"publisher","DOI":"10.7860\/jcdr\/2016\/19338.8465"},{"key":"ref5","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2006.01.007"},{"key":"ref6","doi-asserted-by":"publisher","DOI":"10.3390\/ph14030176"},{"key":"ref7","doi-asserted-by":"publisher","DOI":"10.13140\/rg.2.2.32357.24802"},{"key":"ref8","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.10.070"},{"key":"ref9","doi-asserted-by":"publisher","DOI":"10.1021\/jm0609014"},{"key":"ref10","doi-asserted-by":"publisher","DOI":"10.3390\/ph13010015"},{"key":"ref11","doi-asserted-by":"publisher","DOI":"10.1007\/s10787-998-0026-0"},{"key":"ref12","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-199448050-00008"},{"key":"ref13","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b02857"},{"key":"ref14","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b00611"},{"key":"ref15","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00410"},{"key":"ref16","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201800413"},{"key":"ref17","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01716"},{"key":"ref18","doi-asserted-by":"publisher","DOI":"10.1021\/ol0711117"},{"key":"ref19","doi-asserted-by":"publisher","DOI":"10.1021\/jo400162d"},{"key":"ref20","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.1c00025"},{"key":"ref21","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700824"},{"key":"ref22","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.2839"},{"key":"ref23","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23030674"},{"key":"ref24","doi-asserted-by":"publisher","DOI":"10.1039\/b312154m"},{"key":"ref25","doi-asserted-by":"publisher","DOI":"10.1021\/jo048671t"},{"key":"ref26","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.08.143"},{"key":"ref27","doi-asserted-by":"publisher","DOI":"10.1080\/00397910701750250"},{"key":"ref28","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.201190223"},{"key":"ref29","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2011.614714"},{"key":"ref30","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.1717"},{"key":"ref31","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.05.024"}],"container-title":["Beilstein 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