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    Synthesis of Indolo[3,2-b]carbazoles via an Anomeric-Based Oxidation Process: A Combined Experimental and Computational Strategy

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    Publication date
    2018-04
    Author
    Zolfigol, M.A.
    Khazaei, A.
    Karimitabar, F.
    Hamidi, M.
    Maleki, F.
    Aghabarari, B.
    Sefat, Farshid
    Mozafari, M.
    Keyword
    Indolo[3,2-b]carbazoles
    Synthesis
    Anomeric-Based Oxidation
    Peer-Reviewed
    Yes
    
    Metadata
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    Abstract
    Indolo[3,2-b]carbazole is a molecule of great biological significance, as it is formed in vivo after consumption of cruciferous vegetables. The reaction of 1H-indole and various aldehydes in the presence of a catalytic amount of N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide as an efficient and homogeneous catalyst in acetonitrile at 50°C produces 6,12-disubstituted 5,7-dihydroindolo[2,3-b]carbazole with an in good to excellent yield. The presented technique offers a fast and robust method, by the use of inexpensive commercially available starting materials toward 6,12- disubstituted 5,7-dihydroindolo[2,3-b]carbazole. A new anomeric-based oxidation was kept in mind for the final step of the indolo[2,3-b]carbazoles synthesis. The suggested anomeric-based oxidation mechanism was supported by experimental and theoretical evidences.
    URI
    http://hdl.handle.net/10454/16993
    Version
    No full-text in the repository
    Citation
    Zolfigol MA, Khazaei A, Karimitabar F et al (2018) Synthesis of Indolo[3,2-b]carbazoles via an Anomeric-Based Oxidation Process: A Combined Experimental and Computational Strategy. Journal of Heterocyclic Chemistry. 55(4): 1061-1068.
    Link to publisher’s version
    https://doi.org/10.1002/jhet.3077
    Type
    Article
    Collections
    Engineering and Informatics Publications

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