PMA/SiO₂: An Efficient and Reusable Heterogeneous Catalyst for the Synthesis of β-Acetamidocarbonyl Compounds by Multicomponent Reaction

REFERENCES

• (a) Ugi , I. ; Wernwer , B. ; Domling , A. The chemistry of isocyanides, their multicomponent reactions, and their libraries . Molecules 2003 , 8 , 53 ; (b) Domling , A. The discovery of new isocyanide-based multicomponent reactions . Curr. Opin. Chem. Biol. 2000 , 4 , 318 ; (c) Weber , L. Multicomponent reactions and evolutionary chemistry . Drug Disc. Today 2002 , 7 , 143 .
   Web of Science ®Google Scholar
• Casmir , J. R. ; Turetta , C. ; Ettouati , L. ; Paris , J. First appliction of the Dakins–West reaction to Fmoc chemistry. Tetrahedron Lett. 1995, 36, 4797.
   Google Scholar
• (a) Dahn , U. ; Hagenmaier , H. ; Hohne , H. ; Kong , W. A. ; Wolf , G. ; Zahner , H. Synthesis and biosynthens of substituted tryptanthrins . Arch. Microbiol. 1976 , 107 , 249 ; (b) Kobinaka , K. ; Uramoto , M. ; Nishii , M. ; Kusakabe , H. ; Nakamura , G. ; Isono , K. Chemistry of the neopolyoxins, pyrimidine, and imidazoline nucleoside peptide antibiotics . Agric. Biol. Chem. 1980 , 44 , 1709 .
   PubMed Web of Science ®Google Scholar
• Dakin , H. D. ; West , R. A general reaction of amino acids . J. Biol. Chem. 1928 , 78 , 745 .
   Web of Science ®Google Scholar
• Buchanan , G. L. The Dakins–West reactions . Chem. Soc. Rev. 1988 , 17 , 91 .
   Web of Science ®Google Scholar
• (a) Bhatia , B. ; Reddy , M. M. ; Iqbal , J. Cobalt-catalysed three-component coupling involving ketones or ketoesters, aldehydes, and acetonitrile—A novel one-pot synthesis of β-acetamido ketones . J. Chem. Soc. Chem. Commun. 1994 , 713 ; (b) Mukhopadhyay , B. ; Bhatia , B. : Iqbal , J. Cobalt-catalysed multicomponent condensation route to β-acetamido compound libraries . Tetrahedron Lett. 1997 , 38 , 1083 ; (c) Rao , I. N. ; Prabhakaran , E. N. ; Das , S. K. ; Iqbal , J. Cobalt-catalysed one-pot three-component coupling route to β-acetaamido carbonyl compounds: A general protocol for γ-lactals . J. Org. Chem. 2003 , 68 , 4079 .
   Google Scholar
• Bahulayan , D. ; Das , S. K. ; Iqbal. J. Montmorillonite K-10 clay: An efficient catalyst for the one-pot stereoselective synthesis of β-acetamido ketones . J. Org. Chem. 2003 , 68 , 5735 .
   PubMed Web of Science ®Google Scholar
• Khodaei , M. M. ; Khosropour , A. R. ; Fattabpour , P. A modified procedure for the Dakin–West reation: An efficient and convenient method for a one-pot synthesis of β-acetamido ketones using silica sulfuric acid catalyst . Tetrahedron Lett. 2005 , 46 , 2105 .
   Web of Science ®Google Scholar
• Ghosh , R. ; Maity , S. ; Chakraborty , A. R. ; Chakraborty , S. ; Mukherjee , A. K. ZrOCl2·8H2O: An efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamidoketones . Tetrahedron 2006 , 62 , 4059 .
   Web of Science ®Google Scholar
• Pandey , G. ; Singh , R. P. ; Garg , A. ; Singh , V. K. Synthesis of Mannich-type products via three-component coupling reaction . Tetrahedron Lett. 2005 , 46 , 2137 .
   Web of Science ®Google Scholar
• Ghosh , R. ; Maity , S. ; Chakraborty , A. One-pot multicomponent synthesis of β-acetamido ketones based on BiCl3 generated in situ from the procatalyst BiOCl and acetylchloride . Synlett 2005 , 115 .
   Google Scholar
• Maghsoodlou , M. T. ; Hassankhani , A. ; Shaterian , H. R. ; Habibi- Khorasani , S. M. ; Mosaddegh , E. Zinc oxide as an economical and efficient catalyst for the one-pot preparation of β-acetamidoketones via a four-component condensation . Tetrahedron Lett. 2007 , 48 , 1729 .
   Web of Science ®Google Scholar
• Das , B. ; Reddy , K. R. ; Ramu , R. ; Thirupathi , P. ; Ravikanth , B. Iodine as an efficient catalyst for one-pot multicomponent synthesis of β-acetamido ketones . Synlett 2006 , 1756 .
   Web of Science ®Google Scholar
• (a) Das , B. ; Reddy , K. R. Thirupathi , P. A simple efficient and selective deprotection of t-butyldimethylesilyl (TBDMS) ethers using silica-supported sodium hydrogen sulphate as heterogeneous catalyst . Tetrahedron Lett. 2006 , 47 , 5855 ; (b) Das , B. ; Venkateswarlu , K. ; Krishnaiah , M. ; Harish , H. A highly chemoselective Boc protection of amines using sulphonic acid functionalized silica as an efficient heterogeneous recyclable catalyst . Tetrahedron Lett. 2006 , 47 , 7551 ; (c) Das , B. ; Venkateswarlu , K. ; Krishnaiah , M. ; Harish , H. An efficient, rapid, and regioselective nuclear bromination of aromatics and hetero aromatics with NBS using sulfonic acid functionalized silica as a heterogeneous recyclable catalyst . Tetrahedron Lett. 2006 , 47 , 8693 ; (d) Das , B. ; Thirupathi , P. A highly selective efficient acetylation of alcohols and amines with acetic anhydride using NaHSO4-SiO2 as a heterogeneous catalyst . J. Mol. Catal. A: Chem. 2007 , 269 , 12 .
   Web of Science ®Google Scholar
• Kishore Kumar , G. D. ; Basakaran , S. A facile catalytic and environmentally benign method for the selective deprotection of tert-butyl dimethylesilyl ether mediated by phosphomolybdic acid supported on silica gel. J. Org. Chem. 2005, 70, 4520.
   PubMed Web of Science ®Google Scholar
• Part 145 in the series “Studies on novel synthetic methodologies.”
   Google Scholar