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Sequential Nitrile Amidination–Reduction as a Straightforward Procedure to Selective Linear Polyamine Preparation

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posted on 2023-11-25, 15:43 authored by Antonio Peñas-Sanjuán, Jose J. Chica-Armenteros, Rubén Cruz-Sánchez, Celeste García-Gallarín, Manuel Melguizo
A straightforward strategy toward the efficient synthesis of linear saturated polyamines containing 1,2-diaminoethane and/or 1,3-diaminopropane fragments has been developed. The procedure is based on the chemistry of 5- and 6-membered cyclic amidines, including their efficient synthesis from nitrile precursors and subsequent chemoselective reductive-opening by a borane–dimethyl sulfide complex. This two-step procedure provides a robust methodology for the synthesis of linear polyamine skeletons under nonharsh conditions and free of using selective protective groups or tedious workups.

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