{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,25]],"date-time":"2025-10-25T21:46:01Z","timestamp":1761428761885,"version":"build-2065373602"},"reference-count":24,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2005,7,4]],"date-time":"2005-07-04T00:00:00Z","timestamp":1120435200000},"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":[[2005,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Palladium\u2010catalyzed borylation and Suzuki coupling (BSC) in a one\u2010pot procedure was successfully applied to the synthesis of several \u03b2\u2010substituted dehydrophenylalanines in the benzo[<jats:italic>b<\/jats:italic>]thiophene series, with the stereochemistry of the starting materials being maintained. Bromobenzo[<jats:italic>b<\/jats:italic>]thiophenes bearing an <jats:italic>ortho<\/jats:italic> EDG (OMe or Me) were used as the components to be borylated with pinacolborane, whilst pure stereoisomers of \u03b2\u2010bromodehydrophenylalanines were used as the other Suzuki coupling components. Treatment of the obtained methyl ester of (<jats:italic>Z<\/jats:italic>)\u2010<jats:italic>N<\/jats:italic>\u2010(<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl)\u2010\u03b2\u2010(2,3,5\u2010trimethylbenzo[<jats:italic>b<\/jats:italic>]thien\u20106\u2010yl)dehydrophenylalaninewith Pd(OAc)<jats:sub>2<\/jats:sub> and Cu(OAc)<jats:sub>2<\/jats:sub> in DMF at 160 \u00b0C gave two indole derivatives (1:3), the major product resulting from isomerization and cyclization and the minor product resulting from direct cyclization (thienoindole). Carrying out the reaction at 100 \u00b0C gave the same products in similar amounts. Use of the methyl ester of (<jats:italic>Z<\/jats:italic>)\u2010<jats:italic>N<\/jats:italic>\u2010(<jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl)\u2010\u03b2\u2010(2,3,7\u2010trimethylbenzo[<jats:italic>b<\/jats:italic>]thien\u20106\u2010yl)dehydrophenylalanine as starting material gave only one product, resulting from isomerization and cyclization at 100 \u00b0C. Two of the cyclized compounds were subjected to fluorescence studies; the thienoindole could be useful as a fluorescent probe. Preliminary studies of antimicrobial activity were performed on the precursors and on the cyclized products.<\/jats:p>","DOI":"10.1002\/ejoc.200500040","type":"journal-article","created":{"date-parts":[[2005,7,4]],"date-time":"2005-07-04T11:06:34Z","timestamp":1120475194000},"page":"2951-2957","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Synthesis of \u03b2\u2010Benzo[<i>b<\/i>]thienyldehydrophenylalanine Derivatives by One\u2010Pot Palladium\u2010Catalyzed Borylation and Suzuki Coupling (BSC) and Metal\u2010Assisted Intramolecular Cyclization \u2013 Studies of Fluorescence and Antimicrobial Activity"],"prefix":"10.1002","volume":"2005","author":[{"given":"Ana S.","family":"Abreu","sequence":"first","affiliation":[]},{"given":"Paula M. T.","family":"Ferreira","sequence":"additional","affiliation":[]},{"given":"Maria\u2010Jo\u00e3o R. 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