A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction

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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Main Author: Ibrahim Ali , Noorbatcha
Format: Article
Language:English
Published: Elsevier BV 2004
Subjects:
QD Chemistry
Online Access: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
id iium-34910
recordtype eprints
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
repository_type Digital Repository
institution_category Local University
institution International Islamic University Malaysia
building IIUM Repository
collection Online Access
language English
topic QD Chemistry
spellingShingle QD Chemistry
Ibrahim Ali , Noorbatcha
A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction
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.
format Article
author Ibrahim Ali , Noorbatcha
author_facet Ibrahim Ali , Noorbatcha
author_sort Ibrahim Ali , Noorbatcha
title 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_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_sort tandem highly steroselective fecl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction
publisher Elsevier BV
publishDate 2004
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
first_indexed 2023-09-18T20:50:11Z
last_indexed 2023-09-18T20:50:11Z
_version_ 1777409942603431936

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