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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
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Original Articles

Synthesis of Enaminones in Aqueous Media Using Catalytic Dilute HCl

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Pages 1064-1070 | Received 01 Aug 2009, Published online: 03 Mar 2011

REFERENCES

  • (a) Charushin , V. N. ; Mochulskaya , N. N. ; Andreiko , A. A. ; Filyakova , V. I. ; Kodess , M. I. ; Chupakhin , O. N. Aminovinyl ketones and aminovinyl esters as C—C—N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines . Tetrahedron Lett. 2003 , 44 , 2421 – 2424 ; (b) Savarin , C. G. ; Murry , J. A. ; Dormer , P. G. An expedient synthesis of highly functionalized naphthyridones and quinolines from a common N-aryl pyridinone template . Org. Lett. 2002 , 4 , 2071 – 2074 .
  • Natalie , D. E. ; Donna , S. C. ; Khurana , M. ; Noha , N. S. ; James , P. S. ; Sylvia , J. H. Synthesis and anticonvulsant activity of enaminones, part 7: Synthesis and anticonvulsant evaluation of ethyl 4-[(substituted phenyl)amino]-6-methyl-2-oxocyclohex-3-ene-1-carboxylates and their corresponding 5-methylcyclohex-2-enone derivatives . Eur. J. Med. Chem. 2003 , 38 , 49 – 64 .
  • Bruno , O. ; Schenone , S. ; Ranise , A. ; Bondavalli , F. ; Filippelli , W. Anti-inflammatory agents: New series of N-substituted amino acids with complex pyrimidine structures endowed with antiphlogistic activity . Farmaco 1999 , 54 , 95 – 100 .
  • Farag , A. M. ; Mayhoub , A. S. ; Barakat , S. E. ; Bayomi , A. H. Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives . Bioorg. Med. Chem. 2008 , 16 , 881 – 889 .
  • Cimarelli , C. ; Palmieri , G. Stereoselective reduction of enantiopure β-enamino esters by hydride: A convenient synthesis of both enantiopure β-amino esters. J. Org. Chem. 1996, 61, 5557–5563.
  • Bartoli , G. ; Cimarelli , C. ; Marcantioni , E. ; Palmieri , G. ; Petrini , M. Chemo- and diastereoselective reduction of β-enamino esters: A convenient synthesis of both cis- and trans-γ-amino alcohols and β-amino esters . J. Org. Chem. 1994 , 59 , 5238 – 5335 .
  • Beholz , L. G. ; Benovsky , P. ; Ward , D. L. ; Barta , N. S. Formation of dihydropyridone- and pyridone-based peptide analogs through α-annulation of β-enamino ester and amide substrates with α-amido acrylate derivatives . J. Org. Chem. 1997 , 62 , 1033 – 1042 .
  • David , O. ; Blot , J. ; Bellec , C. ; Fargeau-Bellassoued , M. C. ; Haviari , G. ; Celerier , J.-P. ; Lhommet , G. ; Gramain , J.-C. ; Gardette , D. Enamino ester reduction: A short enantioselective route to pyrrolizidine and indolizidine alkaloids: Synthesis of (+)-laburnine, (+)-tashiromine, and (−)-isoretronecanol . J. Org. Chem. 1999 , 64 , 3122 – 3131 .
  • Baraldi , G. ; Simoni , D. ; Manfredini , S. An improved preparation of enaminones from 1,3-diketones and ammonium acetate or amine acetates . Synthesis 1983 , 902 – 903 .
  • Rechsteiner , B. ; Boullet , T. F. ; Hamelin , J. Synthesis in dry media coupled with microwave irradiation: Application to the preparation of enaminoketones . Tetrahedron Lett. 1993 , 34 , 5071 – 5074 .
  • Arcadi , A. ; Bianchi , G. ; Giuseppe , D. S. ; Marinelli , F. Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles . Green Chem. 2003 , 5 , 64 – 67 .
  • Braibante , M. E. F. ; Braibante , S. ; Missio , L. ; Andricopulo , A. Synthesis and reactivity of β-amino α,β-unsaturated ketones and esters using K-10 montmorillonite . Synthesis 1994 , 898 – 900 .
  • Bartoli , G. ; Bosco , M. ; Locatelli , M. ; Marcantoni , E. ; Melchiorre , P. ; Sambri , L. Highly diastereoselective synthesis of β-hydroxy amides from β-keto amides . Synlett 2004 , 239 – 242 .
  • Khodaei , M. M. ; Khosropour , A. R. ; Kookhazadeh , M. Enamination of β-dicarbonyl compounds catalyzed by CeCl3 · 7H2O at ambient conditions: Ionic liquid and solvent-free media . Synlett 2004 , 1980 – 1984 .
  • Khosropour , A. R. ; Khodaei , M. M. ; Kookhazadeh , M. A mild, efficient, and environmentally friendly method for the regio- and chemoselective synthesis of enaminones using Bi(TFA)3 as a reusable catalyst in aqueous media . Tetrahedron Lett. 2004 , 45 , 1725 – 1728 .
  • Gogoi , S. ; Bhuyan , R. ; Barua , N. C. Iodine-catalyzed conversion of β-dicarbonyl compounds into β-enaminones within a minute under solvent-free conditions . Synth. Commun. 2005 , 35 , 2811 – 2818 .
  • Das , B. ; Venkateswarlu , K. ; Majhi , A. ; Reddy , M. R. ; Reddy , K. N. Highly efficient, mild, and chemo- and stereoselective synthesis of enaminones and enamino esters using silica-supported perchloric acid under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 246 , 276 – 281 .
  • Gholap , A. R. ; Chakor , N. S. ; Daniel , T. ; Lahoti , R. J. ; Srinivasan , K. V. A remarkably rapid regioselective synthesis of β-enaminones using silica chloride in a heterogeneous as well as an ionic liquid in a homogeneous medium at room temperature . J. Mol. Catal. A: Chem. 2006 , 245 , 37 – 46 .
  • Han , G. F. ; Wang , J. J. ; Jiang , G. J. Synthesis of chroman-4-ono[2,3-b]quinolinone derivative . Chin. J. Org. Chem. 2003 , 23 ( 9 ), 1004 .

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