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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 11
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Original Articles

PANI-HBF4: A Reusable Polymer-Based Solid Acid Catalyst for Three-Component, One-Pot Synthesis of 3-Substituted Amino Methyl Indoles Under Solvent-Free Conditions

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Pages 1593-1603 | Received 30 Jun 2010, Published online: 03 Feb 2012

REFERENCES

  • Domling , A. Recent developments in isocyanide-based multicomponent reactions in applied Chemistry . Chem. Rev. 2006 , 106 , 17 – 89 .
  • Tejedor , D. ; Cruz , D. G. ; Exposito , A. S. ; Tellado , J. J. M. ; Armas , P. D. ; Tellado , F. G. Multicomponent domino processes based on the organocatalytic generation of conjugated acetylides: Efficient synthetic manifolds for diversity-oriented molecular construction . Chem. Eur. J. 2005 , 11 , 3502 – 3510 .
  • Ramon , D. J. ; Yus , M. Asymmetric multicomponent reactions (AMCRs): The new frontier . Angew. Chem. Int. Ed. 2005 , 44 , 1602 – 1634 .
  • Simon , C. ; Constantieux , T. ; Rodriguez , J. Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions. Eur. J. Org. Chem. 2004, 4957–4980.
  • Orru , R. V. A. ; Michiel , D. G. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds . Synthesis 2003 , 1471 – 1499 .
  • Bienayme , H. ; Hulme , C. ; Oddon , G. ; Schmitt , P. Maximizing synthetic efficiency: Multicomponent transformations lead the way . Chem. Eur. J. 2000 , 6 , 3321 – 3329 .
  • Ulaczyk-Lesanko , A. ; Hall , D. G. Wanted: New multicomponent reactions for generating libraries of polycyclic natural products . Curr. Opin. Chem. Biol. 2005 , 9 , 266 – 276 .
  • Weber , L. The application of multicomponent reactions in drug discovery . Curr. Med. Chem. 2002 , 9 , 2085 – 2093 .
  • Hulme , H. ; Gore , V. Multicomponent reactions: Emerging chemistry in drug discovery from xylocain to crixivan . Curr. Med. Chem. 2003 , 10 , 51 – 80 .
  • Jiang , B. ; Yang , C. G. ; Wang , J. Enantioselective synthesis for the (−)-antipode of the pyrazinone marine alkaloid, Hamacanthin A . J. Org. Chem. 2001 , 66 , 4865 – 4869 .
  • Zhang , H. ; Larock , R. C. Synthesis of â-and ç-carbolines by the palladium-catalyzed iminoannulation of internal alkynes . Org. Lett. 2001 , 3 , 3083 – 3086 .
  • Sakagami , M. ; Muratake , H. ; Natsume , M. Preparation of alkyl-substituted indoles in the benzene portion, part 12: Enantiospecific synthesis of hapalindole O . Chem. Pharm. Bull. 1994 , 42 , 1393 – 1398.
  • Fukuyama , T. ; Chen , X. Stereo controlled synthesis of (−)-hapalindole G . J. Am. Chem. Soc. 1994 , 116 , 3125 – 3126 .
  • Faulkner , D. J. Marine natural products . Nat. Prod. Rep. 1999 , 16 , 155 – 198 .
  • Lounasmaa , M. ; Tolvanen , A. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit . Nat. Prod. Rep. 2000 , 17 , 175 – 191 .
  • Sundberg , R. J. Indoles ; Academic Press : San Diego , 1996 .
  • Sundberg , R. J. The Chemistry of Indoles ; Academic Press : New York , 1970 .
  • Lézé , M.-P. ; Le Borgne , M. ; Marchand , P. ; Loquet , D. ; Kogler , M. ; Le Baut , G. ; Palusczak , A. ; Hartmann , R. W. 2- and 3-[(Aryl)(azolyl)methyl]indoles as potential non-steroidal aromatase inhibitors . J. Enzyme Inhib. Med. Chem. 2004 , 19 , 549 – 557.
  • Le Borgne , M. L. ; Marchand , P. ; Seiller , B. D. ; Robert , J. M. ; Baut , G. L. ; Hartmann , R. W. ; Palzer , M. New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2, 3, or 5-(a-azolylbenzyl)-IH-indoles . Bioorg. Med. Chem. Lett. 1999 , 9 , 333 – 336 .
  • Deng , J. ; Sanchez , T. ; Neamati , N. ; Briggs , J. M. Dynamic pharmacophore model optimization: Identification of novel HIV-1 integrase inhibitors . J. Med. Chem. 2006 , 49 , 1684 – 1692 .
  • Contractor , R. ; Samudio , I. J. ; Estrov , Z. ; Harris , D. ; McCubrey , J. A. ; Safe , S. H. ; Andreeff , M. ; Konopleva , M. A novel ring-substituted diindolylmethane, 1,1-bis [3′-(5-methoxyindolyl)]-1-(p-t-butyl phenyl) methane, inhibits extra cellular signal-regulated kinase activation and induces apoptosis in acute myelogenous leukemia . Cancer Res. 2005 , 65 , 2890 – 2898 .
  • Saidi , M. R. ; Azizi , N. ; Naimi-Jamal , M. R. Lithium perchlorate–assisted one-pot, three-component aminoalkylation of electron-rich aromatic compounds . Tetrahedron Lett. 2001 , 42 , 8111 – 8113 .
  • Wang , Y. Q. ; Song , J. ; Hong , R. ; Li , H. ; Li , D. Asymmetric friedel–crafts reaction of indoles with imines by an organic catalyst . J. Am. Chem. Soc. 2006 , 128 , 8156 – 8157 .
  • Jia , Y. ; Xie , J. ; Hai-Feng Duan , G. ; Wang , L. ; Zhou , Q. Asymmetric friedel–crafts addition of indoles to n-sulfonyl aldimines: A simple approach to optically active 3-indolyl-methanamine derivatives . Org. Lett. 2006 , 8 , 1621 – 1624 .
  • Grumbach , H. J. ; Arend , M. ; Risch , N. Amino alkylation of electon-rich aromatic componds using performed iminium salts derived from aldehydes other than formaldehyde. Synthesis , 1996, 7, 883–887.
  • Wynne , J. H. ; Stalick , W. M. Synthesis of 3-[(1-aryl)aminomethyl]indoles . J. Org. Chem. 2002 , 67 , 5850 – 5853 .
  • Mi , X. ; Luo , S. ; He , J. ; Cheng , J. Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines . Tetrahedron Lett. 2004 , 45 , 4567 – 4570 .
  • Srihari , P. ; Singh , V. K. ; Bhunia , D. C. ; Yadav , J. S. One-pot, three-component coupling reaction: Solvent-free synthesis of novel 3-substituted indoles catalyzed by PMA–SiO2 . Tetrahedron Lett. 2009 , 50 , 3763 – 3766 .
  • Palaniappan , S. ; John , A. Conjugated polymers as heterogeneous catalyst in organic synthesis . Curr. Org. Chem. 2008 , 12 , 98 – 117 .
  • Palaniappan , S. ; John , A. A novel polyaniline–fluoroboric acid–dodecylhydrogensulfate salt: Versatile reusable polymer-based solid acid catalyst for organic transformations . J. Mol. Catal. A: Chem. 2005 , 233 , 9 – 15 .

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