{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T18:05:23Z","timestamp":1787508323069,"version":"build-2736575974"},"reference-count":54,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2017,7,14]],"date-time":"2017-07-14T00:00:00Z","timestamp":1499990400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2017,7,14]],"date-time":"2017-07-14T00:00:00Z","timestamp":1499990400000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2017,7,14]],"date-time":"2017-07-14T00:00:00Z","timestamp":1499990400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2017,6,24]]},"abstract":"<jats:p>\n                    A new general approach to double nitration of 6,12-di(hetero)aryl-substituted and 6,12-unsubstituted 5,11-dialkyl-5,11-dihydroindolo[3,2-\n                    <jats:italic>b<\/jats:italic>\n                    ]carbazoles by acetyl nitrate has been developed to obtain their 2,8-dinitro and 6,12-dinitro derivatives, respectively. A formation of mono-nitro derivatives (at C-2 or C-6) from the same indolo[3,2-\n                    <jats:italic>b<\/jats:italic>\n                    ]carbazoles has also been observed in several cases. Reduction of 2-nitro and 2,8-dinitro derivatives with zinc powder and hydrochloric acid has afforded 2-amino- and 2,8-diamino-substituted indolo[3,2-\n                    <jats:italic>b<\/jats:italic>\n                    ]carbazoles, while reduction of 6,12-dinitro derivatives under similar reaction conditions has been accompanied by denitrohydrogenation of the latter compounds into 6,12-unsubstituted indolo[3,2-\n                    <jats:italic>b<\/jats:italic>\n                    ]carbazoles. Formylation of 6,12-dinitro derivatives has proved to occur only at C-2, while bromination of these compounds has taken place at both C-2 and C-8 of indolo[3,2-\n                    <jats:italic>b<\/jats:italic>\n                    ]carbazole scaffold. Moreover, 6,12-dinitro-substituted indolo[3,2-\n                    <jats:italic>b<\/jats:italic>\n                    ]carbazoles have been modified by the reactions with\n                    <jats:italic>S<\/jats:italic>\n                    - and\n                    <jats:italic>N<\/jats:italic>\n                    -nucleophiles. Notably, the treatment of 6,12-dinitro compounds with potassium thiolates has resulted in the displacement of both nitro groups, unlike potassium salts of indole or carbazole, which have caused substitution of only one nitro group.\n                  <\/jats:p>","DOI":"10.3762\/bjoc.13.136","type":"journal-article","created":{"date-parts":[[2017,7,14]],"date-time":"2017-07-14T05:52:00Z","timestamp":1500011520000},"page":"1396-1406","source":"Crossref","is-referenced-by-count":9,"title":["Nitration of 5,11-dihydroindolo[3,2-\n                    <i>b<\/i>\n                    ]carbazoles and synthetic applications of their nitro-substituted derivatives"],"prefix":"10.3762","volume":"13","author":[{"given":"Roman A","family":"Irgashev","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nikita A","family":"Kazin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gennady L","family":"Rusinov","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valery N","family":"Charushin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"2086","published-online":{"date-parts":[[2017,7,14]]},"reference":[{"key":"ref1","volume-title":"Organic Electronics II","year":"2012"},{"key":"ref2","volume-title":"Organic Electronics","year":"2013"},{"key":"ref3","doi-asserted-by":"publisher","DOI":"10.1021\/cr068010r"},{"key":"ref4","doi-asserted-by":"publisher","DOI":"10.1021\/cr100052z"},{"key":"ref5","doi-asserted-by":"publisher","DOI":"10.1021\/cr100428a"},{"key":"ref6","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60108k"},{"key":"ref7","doi-asserted-by":"publisher","DOI":"10.1016\/j.orgel.2009.04.019"},{"key":"ref8","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2009.10.022"},{"key":"ref9","doi-asserted-by":"publisher","DOI":"10.1039\/c2jm30207a"},{"key":"ref10","doi-asserted-by":"publisher","DOI":"10.1016\/j.orgel.2012.12.028"},{"key":"ref11","doi-asserted-by":"publisher","DOI":"10.1039\/c4nj00140k"},{"key":"ref12","doi-asserted-by":"publisher","DOI":"10.1016\/j.orgel.2016.12.016"},{"key":"ref13","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2014.06.011"},{"key":"ref14","doi-asserted-by":"publisher","DOI":"10.1039\/b900271e"},{"key":"ref15","doi-asserted-by":"publisher","DOI":"10.1016\/j.orgel.2010.07.011"},{"key":"ref16","doi-asserted-by":"publisher","DOI":"10.1039\/C1JM14891E"},{"key":"ref17","doi-asserted-by":"publisher","DOI":"10.1039\/C4TC01692K"},{"key":"ref18","doi-asserted-by":"publisher","DOI":"10.1016\/j.mencom.2016.11.019"},{"key":"ref19","doi-asserted-by":"publisher","DOI":"10.1021\/jp808536v"},{"key":"ref20","doi-asserted-by":"publisher","DOI":"10.1039\/c3ta11748k"},{"key":"ref21","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA10148D"},{"key":"ref22","doi-asserted-by":"publisher","DOI":"10.1134\/S156009041605016X"},{"key":"ref23","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpowsour.2016.04.043"},{"key":"ref24","doi-asserted-by":"publisher","DOI":"10.1039\/C6PP00286B"},{"key":"ref25","doi-asserted-by":"publisher","DOI":"10.1039\/C6NR01275B"},{"key":"ref26","doi-asserted-by":"publisher","DOI":"10.1016\/1074-5521(95)90090-X"},{"key":"ref27","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2016.06.005"},{"key":"ref28","doi-asserted-by":"publisher","DOI":"10.1016\/j.etap.2016.02.007"},{"key":"ref29","doi-asserted-by":"publisher","DOI":"10.1038\/nature21080"},{"key":"ref30","doi-asserted-by":"publisher","DOI":"10.1007\/s00204-016-1672-4"},{"key":"ref31","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1380713"},{"key":"ref32","doi-asserted-by":"publisher","DOI":"10.1021\/cr200447s"},{"key":"ref33","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21060785"},{"key":"ref34","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00733-4"},{"key":"ref35","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-822347"},{"key":"ref36","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00029-2"},{"key":"ref37","doi-asserted-by":"publisher","DOI":"10.1021\/jo0711337"},{"key":"ref38","doi-asserted-by":"publisher","DOI":"10.1039\/C1OB06298K"},{"key":"ref39","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.02.007"},{"key":"ref40","doi-asserted-by":"publisher","DOI":"10.1021\/jo202677j"},{"key":"ref41","doi-asserted-by":"publisher","DOI":"10.1021\/ol500841b"},{"key":"ref42","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.04.093"},{"key":"ref43","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1560183"},{"key":"ref44","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA11796A"},{"key":"ref45","first-page":"301","volume-title":"Ullmann\u2019s Encyclopedia of Industrial Chemistry","author":"Booth","year":"2000"},{"key":"ref46","doi-asserted-by":"publisher","DOI":"10.1016\/0143-7208(94)00054-6"},{"key":"ref47","doi-asserted-by":"publisher","DOI":"10.1039\/c4nj00011k"},{"key":"ref48","doi-asserted-by":"publisher","DOI":"10.1080\/00397919408012618"},{"key":"ref49","volume-title":"Encyclopedia of Reagents for Organic Synthesis","author":"Louw","year":"2001"},{"key":"ref50","doi-asserted-by":"publisher","DOI":"10.1039\/QR9581200001"},{"key":"ref51","doi-asserted-by":"publisher","DOI":"10.1002\/0471264180.or054.01"},{"key":"ref52","doi-asserted-by":"publisher","DOI":"10.1021\/jo00404a046"},{"key":"ref53","doi-asserted-by":"publisher","DOI":"10.1021\/jo01329a010"},{"key":"ref54","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1980.25"}],"container-title":["Beilstein Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/13\/136","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/content\/pdf\/1860-5397-13-136.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/www.beilstein-journals.org\/bjoc\/content\/13\/1\/136","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/13\/136","content-type":"text\/html","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,6,23]],"date-time":"2021-06-23T12:53:44Z","timestamp":1624452824000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/13\/136"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,7,14]]},"references-count":54,"URL":"https:\/\/doi.org\/10.3762\/bjoc.13.136","archive":["Portico"],"relation":{},"ISSN":["1860-5397"],"issn-type":[{"value":"1860-5397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,7,14]]}}}