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Issue 21, 2018
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Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation–hydrazine cyclization reactions

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Abstract

Here, we report new methodology for synthesizing 2,3-benzodiazepines and their analogues by means of phosphate-assisted acylation reaction of 1-arylpropan-2-ones with a carboxylic acid followed by hydrazine cyclization in a one-pot two-step manner. An unprotected amino group is tolerated in this reaction. This method provides a direct access to 2,3-benzodiazepines containing aromatic 7,8-dimethoxy and 1-p-aminophenyl groups, which are generally considered important for bioactivity. The presence of 3,4-dimethoxy or 3-methoxy substitution on the benzene ring of the 1-arylpropan-2-one is important for high regioselectivity in the acylation reaction.

Graphical abstract: Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation–hydrazine cyclization reactions

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Publication details

The article was received on 23 Mar 2018, accepted on 09 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8OB00708J
Citation: Org. Biomol. Chem., 2018,16, 4013-4020
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    Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation–hydrazine cyclization reactions

    A. Sumita, J. Lee, Y. Otani and T. Ohwada, Org. Biomol. Chem., 2018, 16, 4013
    DOI: 10.1039/C8OB00708J

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