A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction
A conceptually distinctive stereoselective construction of the novel dimer, N-[N'-acetyl-7,7'-bis-(3,4-dimethoxy-phenyl)-7,8,7',8'-tetrahydro-N'H-[8,8']biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-...
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| Format: | Article |
| Language: | English |
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Elsevier BV
2004
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| Online Access: | http://irep.iium.edu.my/34910/ http://irep.iium.edu.my/34910/1/Tetrahed_2004.pdf |
| _version_ | 1848780979404013568 |
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| author | Ibrahim Ali , Noorbatcha |
| author_facet | Ibrahim Ali , Noorbatcha |
| author_sort | Ibrahim Ali , Noorbatcha |
| building | IIUM Repository |
| collection | Online Access |
| description | A conceptually distinctive stereoselective construction of the novel dimer, N-[N'-acetyl-7,7'-bis-(3,4-dimethoxy-phenyl)-7,8,7',8'-tetrahydro-N'H-[8,8']biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AMI calculations. Mechanistic interpretations, consistent with our results, are discussed. |
| first_indexed | 2025-11-14T15:42:16Z |
| format | Article |
| id | iium-34910 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T15:42:16Z |
| publishDate | 2004 |
| publisher | Elsevier BV |
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| spelling | iium-349102014-02-20T01:27:36Z http://irep.iium.edu.my/34910/ A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction Ibrahim Ali , Noorbatcha QD Chemistry A conceptually distinctive stereoselective construction of the novel dimer, N-[N'-acetyl-7,7'-bis-(3,4-dimethoxy-phenyl)-7,8,7',8'-tetrahydro-N'H-[8,8']biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AMI calculations. Mechanistic interpretations, consistent with our results, are discussed. Elsevier BV 2004-12-13 Article PeerReviewed application/pdf en http://irep.iium.edu.my/34910/1/Tetrahed_2004.pdf Ibrahim Ali , Noorbatcha (2004) A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction. Tetrahedron, 60 (51). pp. 11733-11742. ISSN 0040-4020 http://www.journals.elsevier.com/tetrahedron/ DOI: 10.1016/j.tet.2004.10.002 |
| spellingShingle | QD Chemistry Ibrahim Ali , Noorbatcha A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| title | A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| title_full | A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| title_fullStr | A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| title_full_unstemmed | A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| title_short | A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| title_sort | tandem highly steroselective fecl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction |
| topic | QD Chemistry |
| url | http://irep.iium.edu.my/34910/ http://irep.iium.edu.my/34910/ http://irep.iium.edu.my/34910/ http://irep.iium.edu.my/34910/1/Tetrahed_2004.pdf |