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      A truly green synthesis of α-aminonitriles via Strecker reaction

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          Abstract

          Background

          The classical Strecker reaction is one of the simplest and most economical methods for the synthesis of racemic α-aminonitriles (precursor of α-amino acids) and pharmacologically useful compounds.

          Results

          Indium powder in water is shown to act as a very efficient catalyst for one-pot, three-component synthesis of α-aminonitriles from diverse amines, aldehydes and TMSCN. This general rapid method is applicable to a wide range of amines and aldehydes and produces products in excellent yield.

          Conclusions

          The present one-pot, three-component environmentally benign procedure for the synthesis of α-aminonitriles will find application in the synthesis of complex biologically active molecules.

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          Most cited references28

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          Catalytic enantioselective Strecker reactions and analogous syntheses.

          H Gröger (2003)
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            Stereoselective synthesis of beta-lactams with polyaromatic imines: entry to new and novel anticancer agents.

            We present herein stereoselective synthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction. Consistent mechanisms for these results have been advanced. As a measure of cytotoxicity, some of these compounds have been assayed against nine human cancer cell lines. Structure-activity study has revealed that 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-aryl-2-azetidinones have potent anticancer activity. The presence of the acetoxy group at C(3) of the beta-lactams has proven to be obligatory for their anticancer activity.
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              Catalytic Asymmetric Strecker Synthesis. Preparation of Enantiomerically Pure α-Amino Acid Derivatives from Aldimines and Tributyltin Cyanide or Achiral Aldehydes, Amines, and Hydrogen Cyanide Using a Chiral Zirconium Catalyst

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                Author and article information

                Journal
                Org Med Chem Lett
                Org Med Chem Lett
                Organic and Medicinal Chemistry Letters
                Springer
                2191-2858
                2011
                4 October 2011
                : 1
                : 11
                Affiliations
                [1 ]Department of Chemistry, The University of Texas-Pan American, 1201, West University Drive, Edinburg, TX 78539, USA
                Article
                2191-2858-1-11
                10.1186/2191-2858-1-11
                3339329
                22373109
                05cb8708-7684-4b1d-aab7-7194ad312205
                Copyright ©2011 Bandyopadhyay et al; licensee Springer.

                This is an Open Access article distributed under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                : 22 March 2011
                : 4 October 2011
                Categories
                Original

                Pharmaceutical chemistry
                Pharmaceutical chemistry

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