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  • Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

    Author(s)
    Loughlin, Wendy A
    Jenkins, Ian D
    Petersson, Maria J
    Griffith University Author(s)
    Jenkins, Ian D.
    Loughlin, Wendy A.
    Year published
    2013
    Metadata
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    Abstract
    Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducMethods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproduc
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    Journal Title
    The Journal of Organic Chemistry
    Volume
    78
    Issue
    14
    DOI
    https://doi.org/10.1021/jo401082q
    Copyright Statement
    Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Organic chemical synthesis
    Publication URI
    http://hdl.handle.net/10072/53331
    Collection
    • Journal articles

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