L‐Proline Catalyzed Enamination of β‐Dicarbonyl Compounds under Solvent‐free Conditions

A simple, general and efficient method has been developed for synthesis of various β-enamino ketones and esters by reacting β-dicarbonyl compounds with amines using a catalytic amount of L-proline at room temperature under solvent-free conditions in excellent yields.

[1]  Yong-mei Wang,et al.  A General and Efficient Method for the Preparation of β-Enamino Ketones and Esters Catalyzed by Indium Tribromide , 2006 .

[2]  A. Majee,et al.  Tetrahydropyranylation and Depyranylation of Alcohols Catalyzed by Aqueous Zinc Tetrafluoroborate , 2005 .

[3]  K. Rao,et al.  A facile synthesis of 2,3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support , 2005 .

[4]  A. Khosropour,et al.  Enamination of β-Dicarbonyl Compounds Catalyzed by CeCl3·7H2O at ­Ambient Conditions: Ionic Liquid and Solvent-Free Media , 2004 .

[5]  Yuan Gao,et al.  A Convenient and Effective Method for Synthesizing β‐Amino‐α,β‐Unsaturated Esters and Ketones , 2004 .

[6]  C. Kascheres,et al.  Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds , 2004 .

[7]  C. Brandt,et al.  Efficient Synthetic Method for β-Enamino Esters Using Ultrasound , 2004 .

[8]  M. Abdel-Khalik,et al.  Enaminones as building blocks in heterocyclic synthesis: New syntheses of nicotinic acid and thienopyridine derivatives , 2004 .

[9]  B. Štefane,et al.  A New Regio- and Chemoselective Approach to β-Keto Amides and β-Enamino Carboxamides via 1,3,2-Dioxaborinanes , 2004 .

[10]  F. C. D. Silva,et al.  Natural clays as efficient catalysts for obtaining chiral β-enamino esters , 2004 .

[11]  A. Khosropour,et al.  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 , 2004 .

[12]  E. Marcantoni,et al.  Zn(ClO4)2.6H2O as a powerful catalyst for the conversion of β-ketoesters into β-enamino esters , 2004 .

[13]  G. Rosso,et al.  Preparation of beta-enamino carbonylic compounds using microwave radiation/K-10 , 2003 .

[14]  B. Ranu,et al.  Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions , 2003 .

[15]  B. Ranu,et al.  Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions , 2003 .

[16]  G. Bianchi,et al.  Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles , 2003 .

[17]  B. Ranu,et al.  Highly efficient acylation of alcohols, amines and thiols under solvent-free and catalyst-free conditions , 2003 .

[18]  B. Ranu,et al.  A simple and green procedure for the synthesis of α-aminophosphonate by a one-pot three-component condensation of carbonyl compound, amine and diethyl phosphite without solvent and catalyst , 2002 .

[19]  K. Sharpless,et al.  Searching for new reactivity (Nobel lecture). , 2002, Angewandte Chemie.

[20]  Ryoji Noyori,et al.  Asymmetric catalysis: science and opportunities (Nobel lecture). , 2002, Angewandte Chemie.

[21]  B. Ranu,et al.  Unusual Cleavage of Ethers by Thiophenol on the Surface of Silica Gel Impregnated with Indium(III) Chloride under Microwave Irradiation: Efficient Procedure for the Synthesis of Thioethers through Transthioetherification , 2002 .

[22]  J. Wang,et al.  1,2-Aryl and 1,2-Hydride Migration in Transition Metal Complex Catalyzed Diazo Decomposition:  A Novel Approach to α-Aryl-β-enamino Esters , 2001 .

[23]  B. Ranu,et al.  Synthesis of alkyl-substituted pyrroles by three-component coupling of carbonyl compound, amine and nitro-alkane/alkene on a solid surface of silica gel/alumina under microwave irradiation , 2001 .

[24]  B. Ranu,et al.  Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride , 2000 .

[25]  H. A. Stefani,et al.  An Easy Synthesis of Enaminones in Water as Solvent , 2000 .

[26]  E. Kaji,et al.  Stannylene acetal-mediated regioselective open glycosylation of methyl β-d-galactopyranoside and methyl α-l-rhamnopyranoside , 2000 .

[27]  C. Valduga,et al.  The Use of K-10/Ultrasound in the Selective Synthesis of Unsymmetrical β-Enamino Ketones , 1998 .

[28]  A. Zapata,et al.  Synthesis of Enaminones Using Trimethylsilyl Trifluoromethanesulfonate as an Activator. , 1997 .

[29]  A. Lee,et al.  A simple and highly efficient synthesis of β-amino-α, β-unsaturated ester via sonochemical Blaise reaction , 1997 .

[30]  Z. Rappoport The chemistry of enamines , 1994 .

[31]  J. Hamelin,et al.  Synthesis in dry media coupled with microwave irradiation : Application to the preparation of enaminoketones. , 1993 .

[32]  F. Texier-Boullet A simple, convenient and mild synthesis of imines on alumina surface without solvent , 1985 .

[33]  A. Saeed Preparation and molecular structure of new cyclic .beta.-diketone Schiff bases , 1984 .

[34]  S. Manfredini,et al.  An Improved Preparation of Enaminones from 1,3-Diketones and Ammonium Acetate or Amine Acetates , 1983 .

[35]  Yasuhiro Yamamoto,et al.  Nuclear magnetic resonance spectral study of β-aminoenones , 1975 .

[36]  D. R. Parrish,et al.  Asymmetric synthesis of bicyclic intermediates of natural product chemistry , 1974 .

[37]  G. Sauer,et al.  New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures , 1971 .

[38]  F. Pennington,et al.  Reaction of methyl and ethyl 2-cyclopentanonecarboxylates with amines to give carbinolamines, enamines, and adipamides , 1967 .

[39]  D. F. Martin,et al.  Stabilities of Bivalent Metal Complexes of Some B-Ketoimines , 1961 .

[40]  H. Pracejus Organische Katalysatoren, LXI. Asymmetrische Synthesen mit Ketenen, I. Alkaloid‐katalysierte asymmetrische Synthesen von α‐Phenyl‐propionsäureestern , 1960 .

[41]  G. Reynolds,et al.  Reactions of β-Keto Esters with Aromatic Amines. Syntheses of 2- and 4-Hydroxyquinoline Derivatives1 , 1948 .

[42]  W. Marckwald Ueber asymmetrische Synthese , 1904 .