Facile and Green Method for the Synthesis of β-Aminoketone Derivatives in Aqueous Media

Three-component reaction of aromatic aldehyde, 2-naphthalenamine, and 1,2-diphenylethanone in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) at 90 °C gave 3-aryl-3-(naphthalen-2-ylamino)-1,2-diphenylpropan-1-one derivatives. The enol form of 1,2-diphenylethanone was tentatively proposed to participate in the formation of the products. Compared with previous methods, this three-component reaction has the advantages of green solvent, good yields, and operational simplicity.

[1]  S. Kantevari,et al.  Potassium dodecatungstocobaltate trihydrate (K5CoW12O40 · 3H2O): A mild and efficient reusable catalyst for the synthesis of amidoalkyl naphthols in solution and under solvent-free conditions , 2007 .

[2]  S. Kantevari,et al.  Montmorillonite K10 catalyzed efficient synthesis of amidoalkyl naphthols under solvent free conditions , 2007 .

[3]  G. Srihari,et al.  Solvent‐Free One‐Pot Synthesis of Amidoalkyl Naphthols Catalyzed by Silica Sulfuric Acid , 2007 .

[4]  S. D. Samant,et al.  Ultrasound-promoted synthesis of 1-amidoalkyl-2-naphthols via a three-component condensation of 2-naphthol, ureas/amides, and aldehydes, catalyzed by sulfamic acid under ambient conditions. , 2007, Ultrasonics sonochemistry.

[5]  S. D. Samant,et al.  Cation‐Exchanged Resins: Efficient Heterogeneous Catalysts for Facile Synthesis of 1‐Amidoalkyl‐2‐naphthols from One‐Pot, Three‐Component Condensations of Amides/Ureas, Aldehydes, and 2‐Naphthol , 2007 .

[6]  B. Das,et al.  Iodine catalyzed preparation of amidoalkyl naphthols in solution and under solvent-free conditions ☆ , 2007 .

[7]  P. T. Perumal,et al.  A new synthesis of acetamido phenols promoted by Ce(SO4)2 , 2006 .

[8]  A. Khosropour,et al.  A simple and efficient procedure for the synthesis of amidoalkyl naphthols by p-TSA in solution or under solvent-free conditions , 2006 .

[9]  Xianyong Wei,et al.  A simple and clean procedure for the synthesis of polyhydroacridine and quinoline derivatives: reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium , 2005 .

[10]  Tong‐Shuang Li,et al.  One-Pot Clean Synthesis of 1,8-Dioxo-decahydroacridines Catalyzed by p-Dodecylbenezenesulfonic Acid in Aqueous Media , 2004 .

[11]  A. Chan,et al.  New 1,3-amino alcohols derived from ketopinic acid and their application in catalytic enantioselective reduction of prochiral ketones , 1999 .

[12]  D. Enders,et al.  Enantioselective Synthesis ofβ-Amino Sulfones by aza-Michael Addition to Alkenyl Sulfones , 1999 .

[13]  R. Hulst,et al.  Synthesis and Application of New Chiral Ligands for the Asymmetric Borane Reduction of Prochiral Ketones , 1996 .

[14]  S. Knapp.  Synthesis of Complex Nucleoside Antibiotics , 1995 .

[15]  R. Sarges,et al.  Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins. , 1984, Journal of medicinal chemistry.

[16]  A. Spassov,et al.  Proton N.M.R. Spectra and Stereochemistry of Diastereomeric Arylsubstituted β‐Aminoketones , 1980 .