{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T17:46:18Z","timestamp":1760895978367,"version":"build-2065373602"},"reference-count":17,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2003,12,4]],"date-time":"2003-12-04T00:00:00Z","timestamp":1070496000000},"content-version":"vor","delay-in-days":3,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2003,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The methyl ester of \u03b2,\u03b2\u2010dibromo\u2010<jats:italic>N<\/jats:italic>\u2010(<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl)dehydroalanine was synthesized by treating the methyl ester of <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010bis(<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl)dehydroalanine with trifluoroacetic acid, <jats:italic>N<\/jats:italic>\u2010bromosuccinimide and triethylamine. This compound was then used in Suzuki cross\u2010coupling reactions with several (benzo[<jats:italic>b<\/jats:italic>]thienyl)boronic acids to give the corresponding \u03b2,\u03b2\u2010bis(benzo[<jats:italic>b<\/jats:italic>]thienyl)dehydroalanine derivatives in good to high yields (55\u221290 %). After several experiments, the best conditions were shown to be: (benzo[<jats:italic>b<\/jats:italic>]thienyl)boronic acid (5 equiv.), [Pd(PPh)<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>] (20 mol\u00a0%), Na<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> (4 equiv.) in DME\/H<jats:sub>2<\/jats:sub>O (10:1). The Suzuki cross\u2010coupling products were treated with Pd(OAc)<jats:sub>2<\/jats:sub> and Cu(OAc)<jats:sub>2<\/jats:sub> in DMF at 160 \u00b0C to give the (benzo[<jats:italic>b<\/jats:italic>]thienyl)pyrroles in moderate to good yields (25\u221262 %). Other attempts were carried out using only Cu(OAc)<jats:sub>2<\/jats:sub>, the thienylpyrroles being, in some cases, isolated in lower yields. Preliminary fluorescence studies show that the (benzo[<jats:italic>b<\/jats:italic>]thienyl)pyrroles can be used as biomarkers. All of these compounds are non\u2010proteinogenic amino acids that can have biological activity or can be used in conformational studies in order to establish structure\u2010activity relationships. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2003)<\/jats:p>","DOI":"10.1002\/ejoc.200300394","type":"journal-article","created":{"date-parts":[[2003,12,10]],"date-time":"2003-12-10T07:00:28Z","timestamp":1071039628000},"page":"4792-4796","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["New \u03b2,\u03b2\u2010Bis(benzo[<i>b<\/i>]thienyl)dehydroalanine Derivatives: Synthesis and Cyclization"],"prefix":"10.1002","volume":"2003","author":[{"given":"Ana\u00a0S.","family":"Abreu","sequence":"first","affiliation":[]},{"given":"Nat\u00e1lia\u00a0O.","family":"Silva","sequence":"additional","affiliation":[]},{"given":"Paula\u00a0M.\u00a0T.","family":"Ferreira","sequence":"additional","affiliation":[]},{"given":"Maria\u2010Jo\u00e3o\u00a0R.\u00a0P.","family":"Queiroz","sequence":"additional","affiliation":[]},{"given":"Mariano","family":"Venanzi","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2003,12,4]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1988-27503"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199110513"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199312441"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01271-5"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106487h"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200208)2002:15<2524::AID-EJOC2524>3.0.CO;2-W"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"crossref","unstructured":"E. 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