Silica Supported Perchloric Acid: A Convenient and Environmentally Friendly Catalyst for the One-pot Multicomponent Synthesis of β-Acetamido Ketones

A modified Dakin-West one-pot, four-component condensation of an aryl aldehyde, aryl ketone, acetyl chloride and acetonitrile in the presence of silica supported perchloric acid as an active, inexpensive, recoverable and recyclable catalyst is reported for the synthesis of β-acetamido ketones under mechanical stirring and ultrasonic irradiation conditions. This system has advantages of short reaction times, good to excellent yields and the ability to carry out the large scale reactions. The use of ultrasound increases the rate of reactions compared with reactions at reflux conditions.

[1]  P. T. Perumal,et al.  Cerium(IV) sulfate catalyzed simple and convenient synthesis of β-acetamidocarbonyl compounds , 2009 .

[2]  A. Tiwari,et al.  Reduction in post-prandial hyperglycemic excursion through alpha-glucosidase inhibition by beta-acetamido carbonyl compounds. , 2008, Bioorganic & medicinal chemistry letters.

[3]  I. Mohammadpoor‐Baltork,et al.  Ultrasound-assisted thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and DDQ. , 2008, Ultrasonics sonochemistry.

[4]  F. Moghaddam,et al.  ZnO nanoparticles: An efficient nanocatalyst for the synthesis of β-acetamido ketones/esters via a multi-component reaction , 2008 .

[5]  Rajashaker Bantu,et al.  SnCl2·2H2O-catalyzed efficient synthesis of β-acetamido ketones and β-acetamido ketoesters under solvent-free conditions , 2007 .

[6]  F. Bamoharram,et al.  Sulfamic acid as a cost-effective catalyst instead of metal-containing acids for the one-pot synthesis of β-acetamido ketones , 2007 .

[7]  M. R. Islami,et al.  One-Pot Synthesis of β-Acetamido Ketones Using Aluminum Hydrogen Sulfate as a Reusable Catalyst , 2007 .

[8]  B. Lingaiah,et al.  Perfluorinated resin-sulfonic acid (Nafion-H): an efficient, environment friendly and recyclable heterogeneous catalyst for the one-pot multicomponent synthesis of β-acetamido ketones , 2007 .

[9]  A. T. Khan,et al.  Iron(III) chloride-catalyzed convenient one-pot synthesis of β-acetamido carbonyl compounds , 2007 .

[10]  M. Krishnaiah,et al.  A simple and efficient one-pot synthesis of β-acetamido carbonyl compounds using sulfated zirconia as a heterogeneous recyclable catalyst , 2007 .

[11]  S. Kantevari,et al.  HClO4–SiO2 and PPA–SiO2 catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free conditions: Scope and limitations , 2007 .

[12]  G. Pathuri,et al.  HClO4–SiO2 as a novel and recyclable catalyst for the one-pot synthesis of homoallylic amines , 2007 .

[13]  S. Kantevari,et al.  Highly efficient, one-pot, solvent-free synthesis of tetrasubstituted imidazoles using HClO4–SiO2 as novel heterogeneous catalyst , 2007 .

[14]  A. M. Petrosyan.  Vibrational spectra of l-histidine perchlorate and l-histidine tetrafluoroborate , 2007 .

[15]  F. Bamoharram,et al.  H6P2W18O62: An efficient and reusable catalyst for one-pot synthesis of β-acetamido ketone and esters , 2007 .

[16]  S. Kantevari,et al.  Potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O): A mild and efficient reusable catalyst for the synthesis of β-acetamido ketones under solvent-free conditions , 2007 .

[17]  N. Joshi,et al.  HClO4–SiO2 as a novel and recyclable catalyst for the synthesis of bis-indolylmethanes and bis-indolylglycoconjugates , 2007 .

[18]  Md. Asif Ali,et al.  CeCl3·7H2O: an efficient and reusable catalyst for the preparation of β-acetamido carbonyl compounds by multi-component reactions (MCRs) , 2006 .

[19]  P. Gogate,et al.  Process intensification using cavitation: optimization of oxidation conditions for synthesis of sulfone. , 2006, Ultrasonics sonochemistry.

[20]  Ankush V. Biradar,et al.  An Efficient Method for the Synthesis of Acylals from Aldehydes Using Silica‐Supported Perchloric Acid (HClO4—SiO2). , 2006 .

[21]  A. M. Petrosyan.  Vibrational spectra of L-arginine tetrafluoroborate and L-arginine perchlorate , 2006 .

[22]  A. Misra,et al.  Mild and efficient method for the cleavage of benzylidene acetals using HClO4-SiO2 and direct conversion of acetals to acetates , 2006 .

[23]  C. Rao,et al.  An efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation using heterogeneous catalyst under solvent-free conditions , 2006 .

[24]  E. Rafiee,et al.  The silica supported H3PW12O40 (a heteropoly acid) as an efficient and reusable catalyst for a one-pot synthesis of β-acetamido ketones by Dakin-West reaction , 2005 .

[25]  V. Singh,et al.  Synthesis of Mannich type products via a three-component coupling reaction , 2005 .

[26]  A. Khosropour,et al.  A modified procedure for the Dakin–West reaction: an efficient and convenient method for a one-pot synthesis of β-acetamido ketones using silica sulfuric acid as catalyst , 2005 .

[27]  A. Misra,et al.  Ferrier Rearrangement Catalyzed by HClO 4 -SiO 2 : Synthesis of 2,3-Unsaturated Glycopyranosides , 2005 .

[28]  Jieping Zhu,et al.  Multicomponent Reactions: ZHU:MULTICOMPONENT REACTIONS O-BK , 2005 .

[29]  D. Enders,et al.  Diastereo- and enantioselective synthesis of differently N, O-protected 1,3-amino alcohols with three neighbouring stereogenic centers , 2004 .

[30]  H. Zähner,et al.  Stoffwechselprodukte von Mikroorganismen , 2004, Archives of Microbiology.

[31]  A. Chakraborti,et al.  Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. , 2003, Chemical communications.

[32]  J. Iqbal,et al.  Montmorillonite K10 clay: an efficient catalyst for the one-pot stereoselective synthesis of beta-acetamido ketones. , 2003, The Journal of organic chemistry.

[33]  J. Iqbal,et al.  Cobalt-catalyzed one-pot three-component coupling route to β-acetamido carbonyl compounds: A general synthetic protocol for γ-lactams , 2003 .

[34]  U. Bora,et al.  A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction. , 2003, Organic letters.

[35]  J. Bower,et al.  A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines. , 2002, Chemical communications.

[36]  I. Ugi.  Recent progress in the chemistry of multicomponent reactions , 2001 .

[37]  A. Dömling,et al.  One-pot synthesis and biological evaluation of aspergillamides and analogues. , 2000, Bioorganic & medicinal chemistry letters.

[38]  P. Eilbracht,et al.  Tandem Reaction Sequences under Hydroformylation Conditions: New Synthetic Applications of Transition Metal Catalysis. , 1999, Chemical reviews.

[39]  F. Hegelund,et al.  The ν5Band of HClO4 , 1998 .

[40]  T. Mason.  Ultrasound in synthetic organic chemistry , 1998 .

[41]  J. Iqbal,et al.  Cobalt catalyzed multiple component condensation route to β-acetamido carbonyl compound libraries , 1997 .

[42]  S. Fustero,et al.  1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and Bx , 1993 .

[43]  L. Castedo,et al.  A new synthesis of 4-aryl-2-benzazepine-1,5-diones , 1993 .

[44]  P. Laszlo.  Solid-supported Oxidants , 1991 .

[45]  Jean-Louis Luche,et al.  Sonochemistry: the use of ultrasonic waves in synthetic organic chemistry , 1989 .

[46]  A. Fatiadi.  The Classical Permanganate Ion: Still a Novel Oxidant in Organic Chemistry , 1987 .

[47]  T. Mason,et al.  Sonochemistry. Part 1—The physical aspects , 1987 .

[48]  S. Rault,et al.  Cyclisation de l'acide amino-3 (thienyl-3)-3 propionique en aminocyclopentathiophenes , 1986 .

[49]  P. Jeffs,et al.  Total syntheses of (.+-.)-mesembrine, (.+-.)-joubertinamine, and (.+-.)-N-demethylmesembrenone , 1983 .

[50]  F. Menger,et al.  OXIDATIONS WITH SOLID POTASSIUM PERMANGANATE , 1979 .