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  • Dibenzo[b,f]pyrazolo[1,5-d][1,4]oxazepines: facile construction of a rare heterocyclic system via tandem aromatic nucleophilic substitution - Smiles rearrangement – denitrocyclization

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    Author(s)
    V. Sapegin, Alexander
    A. Kalinin, Stanislav
    V. Smirnov, Alexey
    V. Dorogov, Mikhail
    Krasavin, Mikhail
    Griffith University Author(s)
    Krasavin, Mikhail
    Year published
    2012
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    Abstract
    Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylforrmamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement-denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer.Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylforrmamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement-denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer.
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    Journal Title
    Synthesis: Journal of Synthetic Organic Chemistry
    Volume
    44
    DOI
    https://doi.org/10.1055/s-0031-1289789
    Copyright Statement
    © 2012 Georg Thieme Verlag. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. The definitive version is available at www.thieme-connect.com
    Subject
    Medicinal and Biomolecular Chemistry not elsewhere classified
    Analytical Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/50041
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    • Journal articles

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