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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 13
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Original Articles

KG-60-Piperazine as a New Heterogeneous Catalyst for Gewald Three-Component Reaction

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Pages 1859-1864 | Received 15 Dec 2011, Published online: 04 Apr 2013

REFERENCES

  • Gewald , K. ; Schinke , E. ; Böttcher , H. Heterocyclen aus CH-aciden nitrilen, VIII: 2-Amino-thiophene aus methylenaktiven nitrilen, carbonylverbindungen und schwefel . Chem. Ber. 1966 , 99 , 94 – 100 .
  • Gewald , K. Zur Reaktion von α -oxo-mercaptanen mit nitrilen . Angew. Chem. 1961 , 73 , 114 .
  • Naumann , B. ; Böhm , R. ; Fülöp , F. ; Bernáth , G. Preparation of new trifunctional thiophene derivatives . Pharmazie 1996 , 51 , 4 – 6 .
  • Hallas , G. ; Choi , J.-H. Synthesis and spectral properties of azo dyes derived from 2-aminothiophenes and 2-aminothiazoles . Dyes Pigm. 1999 , 42 , 249 – 265 .
  • Sridhar , M. ; Rao , R. M. ; Baba , N. H. K. ; Kumbhare , R. M. Microwave-accelerated Gewald reaction: Synthesis of 2-aminothiophenes . Tetrahedron Lett. 2007 , 48 , 3171 – 3172 .
  • Hoener , A. P. F. ; Henkel , B. ; Gauvin , J.-C. Novel one-pot microwave-assisted Gewald synthesis of 2-acyl amino thiophenes on solid support. Synlett 2003, 63–66.
  • Huang , W. ; Li , J. ; Tang , J. ; Liu , H. , Shen , J. ; Jiang , H. Microwave-assisted synthesis of 2-amino-thiophene-3-carboxylic derivatives under solvent-free conditions . Synth. Commun. 2005 , 35 , 1351 – 1357 .
  • Mekheimer , R. A. ; Ameen , M. A. ; Sadek , K. U. Solar thermochemical reactions II: Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy . Chin. Chem. Lett. 2008 , 19 , 788 – 790 .
  • Hu , Y. ; Chen , Z.-C. ; Le , Z.-G. ; Zheng , Q.-G. Organic reactions in ionic liquids: Gewald synthesis of 2-aminothiophenes catalyzed by ethylenediammonium diacetate . Synth. Commun. 2004 , 34 , 3801 – 3806 .
  • Feroci , M. ; Chiarotto , I. ; Rossi , L. ; Inesi , A. Activation of elemental sulfur by electrogenerated cyanomethyl anion: Synthesis of substituted 2-aminothiophenes by the Gewald reaction . Adv. Synth. Catal. 2008 , 350 , 2740 – 2746 .
  • (a) Notestein , J. M. ; Katz , A. Enhancing heterogeneous catalysis through cooperative hybrid organic–inorganic interfaces . Chem. Eur. J. 2006 , 12 , 3954 – 3965 ; (b) Tada , M. ; Iwasawa , Y. Advanced chemical design with supported metal complexes for selective catalysis . Chem. Commun. 2006 , 2833 – 2844 ; (c) Corma , A. ; Garcia , H. Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis . Adv. Synth. Catal. 2006 , 348 , 1391 – 1412 ; (d) Song , C. E. ; Kim , D. H. ; Choi , D. S. Chiral organometallic catalysts in confined nanospaces: Significantly enhanced enantioselectivity and stability . Eur. J. Inorg. Chem. 2006 , 2927 – 2935 ; (e) Dioos , B. M. L. ; Vankelecom , I. F. J. ; Jacobs , P. A. Aspects of immobilisation of catalysts on polymeric supports . Adv. Synth. Catal. 2007 , 348 , 1413 – 1446 .
  • Leznoff , C. C. The use of insoluble polymer supports in organic chemical synthesis . Chem. Soc. Rev. 1974 , 3 , 65 – 85 .
  • Shimizu , K.-I. ; Suzuki , H. ; Hayashi , E. ; Kodama , T. ; Tsuchiya , Y. ; Hagiwara , H. ; Kitayama , Y. Catalytic direct 1,4-conjugate addition of aldehydes to vinylketones on secondary amines immobilised in FSM-16 silica . Chem. Commun. 2002 , 1068 – 1069 .
  • Angeletti , E. ; Canepa , C. ; Martinetti , G. ; Venturello , P. Silica gel functionalized with amino groups as a new catalyst for Knoevenagel condensation under heterogeneous catalysis conditions . Tetrahedron Lett. 1988 , 29 , 2261 – 2264 .
  • Ballini , R. ; Bosica , G. ; Livi , D. ; Palmieri , A. ; Maggi , R. ; Sartori , G. Use of heterogeneous catalyst KG-60-NEt2 in Michael and Henry reactions involving nitroalkanes . Tetrahedron Lett. 2003 , 44 , 2271 – 2273 .
  • Motokura , K. ; Tomita , M. ; Tada , M. ; Iwasawa , Y. Michael reactions catalyzed by basic alkylamines and dialkylaminopyridine immobilized on acidic silica–alumina surfaces . Top. Catal. 2009 , 52 , 579 – 585 .
  • Puterová , Z. ; Krutošíková , A. ; Végh , D. Gewald reaction: Synthesis, properties, and applications of substituted 2-aminothiophenes . Arkivoc 2010 , 1 , 209 – 246 .
  • Espinola , J. G. P. ; Arakaki , L. N. H. ; de Oliveira , S. F. ; da Fonseca , M. G. ; Filho , J. A. A. C. ; Airoldi , C. Some thermodynamic data of the energetics of the interaction cation-piperazine immobilized on silica gel . Colloids Surf. A 2003 , 221 , 101 – 108 .
  • Gewald , K. Heterocyclen aus CH-aciden nitrilen, VII: 2-Aminothiophene aus α-oxo-mercaptanen und methylenaktiven nitrilen . Chem. Ber. 1965 , 98 , 3571 – 3577 .
  • Foye , W. O. ; Mickles , J. ; Boyce , G. M. Antiradiation compounds, XIV: Dithiocarbamates of aminothiophenes . J. Pharm. Sci. 1970 , 59 , 1348 – 1350 .
  • Manhas , M. S. ; Rao , V. V. ; Setheraman , P. A. ; Succardi , D. ; Pazdera , J. Synthesis of thieno- and furo-pyrimidinethiones . J. Chem. Soc. C 1969 , 1937 – 1939 .

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