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Modifications of carboxyindoles on solid phase

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Tois, Jan
dc.date.accessioned 2012-02-10T09:24:43Z
dc.date.available 2012-02-10T09:24:43Z
dc.date.issued 2003-10-24
dc.identifier.isbn 951-22-6893-0
dc.identifier.issn 1236-2999
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/2191
dc.description.abstract Different solid phase modifications were studied in order to develop new and simple routes for pharmaceutically interesting highly substituted carboxyindoles. A convenient method for the preparation of 5-substituted 2-carboxyindoles and three novel direct functionalization methods for carboxyindoles were developed during this study. 5-Nitro-2-carboxyindole was synthesized easily in three steps from commercially available inexpensive 4-nitro-aniline. Through attachment of this template to solid phase followed by reduction, reductive amination, N-alkylation and cleavage, a small library of differently substituted carboxyindoles were obtained. Solid phase brominations were studied followed by palladium catalyzed Suzuki-coupling. This technology offers an efficient and selective method to introduce bromine and a new C-C-bond to 3-position of polymer bound 2-carboxyindoles. Formylation studies were also succesfull. By utilizing Vilsmeier formylation a new C-C-bond was obtained direcly and selectively at the 3-position of polymer bound 2-carboxyindoles. In solid phase metalation studies of 5-carboxyindoles a 4-position functionalization was achieved in 80 % regioselectivity. Despite the moderate regioselectivity it is obvious that ring lithiation can be adopted to solid phase. en
dc.format.extent 58
dc.format.mimetype application/pdf
dc.language.iso en en
dc.publisher Helsinki University of Technology en
dc.publisher Teknillinen korkeakoulu fi
dc.relation.ispartofseries Organic chemistry report en
dc.relation.ispartofseries 3/2003 en
dc.relation.haspart Tois J., Franzén R., Aitio O., Huikko K. and Taskinen J., 2000. Preparation of 5-substituted 2-carboxyindoles on solid support. Tetrahedron Letters 41, No. 14, pages 2443-2446.
dc.relation.haspart Tois J., Franzén R., Aitio O., Laakso I., Huuskonen J. and Taskinen J., 2001. Solid-phase bromination and Suzuki coupling of 2-carboxyindoles. Combinatorial Chemistry & High Throughput Screening 4, No. 6, pages 521-524.
dc.relation.haspart Tois J., Franzén R., Aitio O., Laakso I. and Kylänlahti I., 2001. Vilsmeier formylation of 2-carboxyindoles and preparation of O-benzylhydroxyureas on solid phase. Journal of Combinatorial Chemistry 3, No. 6, pages 542-545.
dc.relation.haspart Tois J. and Koskinen A., 2003. Solid-phase lithiation of 5-carboxyindoles. Tetrahedron Letters 44, No. 10, pages 2093-2095.
dc.relation.haspart Tois J., Franzén R. and Koskinen A., 2003. Synthetic approaches towards indoles on solid phase recent advances and future directions. Tetrahedron 59, No. 29, pages 5395-5405.
dc.subject.other Chemistry en
dc.title Modifications of carboxyindoles on solid phase en
dc.type G5 Artikkeliväitöskirja fi
dc.description.version reviewed en
dc.contributor.department Department of Chemical Technology en
dc.contributor.department Kemian tekniikan osasto fi
dc.subject.keyword carboxyindoles en
dc.subject.keyword solid phase synthesis en
dc.subject.keyword direct functionalization en
dc.subject.keyword Vilsmeier formylation en
dc.subject.keyword lithiation en
dc.subject.keyword bromination en
dc.identifier.urn urn:nbn:fi:tkk-001618
dc.type.dcmitype text en
dc.type.ontasot Väitöskirja (artikkeli) fi
dc.type.ontasot Doctoral dissertation (article-based) en
dc.contributor.lab Laboratory of Organic Chemistry en
dc.contributor.lab Orgaanisen kemian laboratorio fi

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