{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T16:07:00Z","timestamp":1775232420613,"version":"3.50.1"},"reference-count":14,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2004,9,16]],"date-time":"2004-09-16T00:00:00Z","timestamp":1095292800000},"content-version":"vor","delay-in-days":0,"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":[[2004,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Several phenylacetylenes were coupled under Sonogashira cross\u2010coupling conditions with the methyl esters of <jats:italic>N<\/jats:italic>\u2010(<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl)\u2010(<jats:italic>E<\/jats:italic>)\u2010\u03b2\u2010bromo\u2010 or \u2010\u03b2,\u03b2\u2010dibromodehydroalanine, to give \u03b2\u2010substituted or \u03b2,\u03b2\u2010disubstituted dehydroalanines, respectively. The \u03b2\u2010substituted dehydroalanines were obtained in good to high yields (60\u221290%) under the usual Sonogashira conditions (1 equiv. of the phenylacetylene, 1 mol\u00a0% of [Pd(PPh<jats:sub>3<\/jats:sub>)<jats:sub>4<\/jats:sub>], 2 mol\u00a0% of CuI, 18 equiv. of NEt<jats:sub>3<\/jats:sub> in acetonitrile, 24\u00a0h at room temp.), with retention of stereochemistry. The \u03b2,\u03b2\u2010disubstituted dehydroalanines were, in turn, obtained in moderate to good yields (44\u221263%) under modified Sonogashira conditions (4 equiv. of the phenylacetylene,10 mol\u00a0% of [PdCl<jats:sub>2<\/jats:sub>(PPh<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>], 20 mol\u00a0% of CuI, 1.4 equiv. of Cs<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> in acetonitrile, 2\u00a0h at reflux). In the latter reactions, some phenylacetylene dimer and the (<jats:italic>E<\/jats:italic>) isomer of the monosubstituted coupled products were also isolated to some extent. The Sonogashira products obtained from the 4\u2010bromophenylacetylene were allowed to react with functionalized benzo[<jats:italic>b<\/jats:italic>]thiophenes under C\u2212C or C\u2212N palladium\u2010catalyzed cross\u2010coupling conditions. Preliminary fluorescence studies were performed for mono\u2010 and disubstituted (4\u2010aminophenyl)acetylenic dehydroamino acids and for the benzo[<jats:italic>b<\/jats:italic>]thiophene derivatives. The results showed that some of the dehydroalanines prepared can be used as fluorescent probes. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)<\/jats:p>","DOI":"10.1002\/ejoc.200400145","type":"journal-article","created":{"date-parts":[[2004,9,16]],"date-time":"2004-09-16T08:03:02Z","timestamp":1095321782000},"page":"3985-3991","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Sonogashira Cross\u2010Couplings of Dehydroamino Acid Derivatives and Phenylacetylenes"],"prefix":"10.1002","volume":"2004","author":[{"given":"Ana\u00a0S.","family":"Abreu","sequence":"first","affiliation":[]},{"given":"Paula\u00a0M.\u00a0T.","family":"Ferreira","sequence":"additional","affiliation":[]},{"given":"Maria\u2010Jo\u00e3o\u00a0R.\u00a0P.","family":"Queiroz","sequence":"additional","affiliation":[]},{"given":"Emanuela","family":"Gatto","sequence":"additional","affiliation":[]},{"given":"Mariano","family":"Venanzi","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2004,9,16]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300103"},{"key":"e_1_2_6_2_2","first-page":"1077","author":"Stanovick B.","year":"2000","journal-title":"Synlett"},{"key":"e_1_2_6_3_2","doi-asserted-by":"crossref","unstructured":"J. Svete J. Heterocycl. Chem.2002 39 437\u2212454 and references cited therein.","DOI":"10.1002\/jhet.5570390302"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300394"},{"key":"e_1_2_6_5_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_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200390212"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)00564-1"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/b001538p"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)10197-1"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol034360d"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0162421"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(02)01158-0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(02)01262-7"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr940745l"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.200400145","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.200400145","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T00:16:54Z","timestamp":1760401014000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.200400145"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2004,9,16]]},"references-count":14,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2004,10]]}},"alternative-id":["10.1002\/ejoc.200400145"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.200400145","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2004,9,16]]},"assertion":[{"value":"2004-03-04","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2004-09-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}