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An Efficient Selective Reduction of Aromatic Azides to Amines Employing BF3ˇOEt2/NaI: Synthesis of Pyrrolobenzodiazepines

Ahmed Kamal*, N. Shankaraiah, N. Markandeya, Ch. Sanjeeva Reddy

*Chemical Biology, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India, Email:

A. Kamal, N. Shankaraiah, N. Markandeya, Ch. S. Reddy, Synlett, 2008, 1297-1300.

DOI: 10.1055/s-2008-1072742

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A selective and facile method allows the reduction of aromatic azides to amines by employing borontrifluoride diethyl etherate and sodium iodide. This methodology has been applied towards the preparation of biologically important imine-containing pyrrolobenzodiazepines and their dilactams through an intramolecular reductive-cyclization process.

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Key Words

pyrrolo[2,1-c][1,4]benzodiazepines, boron trifluoride diethyl etherate, sodium iodide, intramolecular reductive-cyclization, reduction of azides

ID: J60-Y2008-1280