{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T17:48:45Z","timestamp":1760896125510},"reference-count":15,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2009,3,11]],"date-time":"2009-03-11T00:00:00Z","timestamp":1236729600000},"content-version":"vor","delay-in-days":2871,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Journal of Heterocyclic Chem"],"published-print":{"date-parts":[[2001,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The synthesis of new methylated thieno[2,3\u2010a] and [3,2\u2010b]carbazoles (5) (R=H) was achieved by a palladium\u2010catalyzed cross\u2010coupling, intramolecular reductive cyclization sequence of reactions. The cyclization precursors 6\u2010(2\u2032\u2010nitrophenyl)benzo[b]thiophenes <jats:bold>(3)<\/jats:bold> were obtained by Suzuki cross\u2010coupling of 6\u2010boronated methylbenzo[<jats:italic>b<\/jats:italic>]thiophenes intermediates <jats:bold>(2)<\/jats:bold> with 2\u2010bromo or iodonitrobenzene. The boronated intermediates <jats:bold>(2)<\/jats:bold> were prepared <jats:italic>via<\/jats:italic> bromine\u2010lithium exchange followed by boron transmetalation and coupled <jats:italic>in situ<\/jats:italic> using Pd(OAc)<jats:sub>2<\/jats:sub> giving thus a \u201cone\u2010pot\u201d three steps reaction from the 6\u2010bromobenzo[<jats:italic>b<\/jats:italic>]thio\u2010phenes <jats:bold>(1)<\/jats:bold> to the cyclization precursors <jats:bold>(3)<\/jats:bold>. In the reductive cyclization step, <jats:italic>N<\/jats:italic>\u2010ethylthienocarbazoles <jats:bold>(5)<\/jats:bold> (R=Et) were also obtained. Several experiments have been made varying the amount of triethylphosphite and the time of reaction, to avoid their formation.<\/jats:p>","DOI":"10.1002\/jhet.5570380334","type":"journal-article","created":{"date-parts":[[2009,3,11]],"date-time":"2009-03-11T11:28:28Z","timestamp":1236770908000},"page":"749-754","source":"Crossref","is-referenced-by-count":20,"title":["Synthesis of new methylated thieno[2,3\u2010<i>a<\/i>] and [3,2\u2010<i>b<\/i>]carbazoles by reductive cyclization of 6\u2010(2\u2032\u2010Nitrophenyl)benzo[<i>b<\/i>]thiophenes obtained by palladium\u2010catalyzed cross\u2010coupling isabel"],"prefix":"10.1002","volume":"38","author":[{"given":"C. F. R.","family":"Ferreira","sequence":"first","affiliation":[]},{"given":"Maria\u2010Jo\u00e3o R. P.","family":"Queiroz","sequence":"additional","affiliation":[]},{"given":"Gilbert","family":"Kirsch","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2009,3,11]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9790800563"},{"key":"e_1_2_1_2_3","doi-asserted-by":"publisher","DOI":"10.1021\/cr950066q"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH9672715"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/0891-5849(90)90067-S"},{"key":"e_1_2_1_5_2","unstructured":"M\u2010J. R. P.QueirozandG.Kirsch 16th International Congress of Heterocyclic Chemistry August Bozeman U.S. Abstr. POII\u2010220 (1997)."},{"key":"e_1_2_1_6_2","doi-asserted-by":"crossref","unstructured":"F. M. C.Peixoto M.\u2010J. R. P.QueirozandG.Kirsch J. Chem. Res. 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