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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 1
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Original Articles

Fast, Solvent-Free, Microwave-Promoted Friedländer Annulation with a Reusable Solid Catalyst

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Pages 120-128 | Received 20 Dec 2008, Published online: 09 Dec 2009

REFERENCES

  • Dewick , P. M. Medicinal Natural Products: A Biosynthetic Approach ; Wiley , Chichester , UK 2002 .
  • Michael , J. P. Quinoline, quinazoline, and acridone alkaloids . Nat. Prod. Rep. 1997 , 14 , 605 – 618 .
  • Markees , D. G. ; Dewey , V. C. ; Kidder , G. W. Antiprotozoal 4-aryloxy-2-aminoquinolines and related compounds . J. Med. Chem. 1970 , 13 , 324 – 326 .
  • Campbell , S. F. ; Hardstone , J. D. ; Palmer , M. J. 2,4-Diamino-6,7-dimethoxyquinoline derivatives as α 1-adrenoceptor antagonists and antihypertensive agents . J. Med. Chem. 1988 , 31 , 1031 – 1035 .
  • Giardina , G. A. M. ; Raveglia , L. F. ; Grugny , M. ; Sarau , H. M. ; Farina , C. ; Medhurst , A. D. ; Graziani , D. ; Schmidt , D. B. ; Rigolio , R. ; Luttmann , M. ; Cavagnera , S. ; Foley , J. J. ; Vecchietti , V. ; Hay , D. W. P. Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor, 2: Identification of (S)-N-(1-phenylpropyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (SB 223412) . J. Med. Chem. 1999 , 42 , 1053 – 1065 .
  • Ko , T. C. ; Hour , M. J. ; Lien , J. C. ; Teng , C. M. ; Lee , K. H. ; Kuoa , S. C. ; Huang , L. J. Synthesis of 4-alkoxy-2-phenylquinoline derivatives as potent antiplatelet agents . Bioorg. Med. Chem. Lett. 2001 , 11 , 279 – 282 .
  • Zhang , X. ; Shetty , A. S. ; Jenekhe , S. A. Electroluminescence and photophysical properties of polyquinolines . Macromolecules 1999 , 32 , 7422 – 7429 .
  • Jenekhe , S. A. ; Lu , L. ; Alam , M. M. New conjugated polymers with donor–acceptor architectures: Synthesis and photophysics of carbazole-quinoline and phenothiazine-quinoline copolymers and oligomers exhibiting large intramolecular charge transfer . Macromolecules 2001 , 34 , 7315 – 7324 .
  • Agrawal , A. K. ; Jenekhe , S. A. Synthesis and processing of heterocyclic polymers as electronic, optoelectronic, and nonlinear-optical materials, 3: New conjugated polyquinolines with electron-donor or electron-acceptor side groups . Chem. Mater. 1993 , 5 , 633 – 640 .
  • Jegou , G. ; Jenekhe , S. A. Highly fluorescent poly(arylene ethynylene)s containing quinoline and 3-alkylthiophene. Macromolecules 2001, 34, 7926–7928.
  • Cho , C. S. ; Kim , B. T. ; Kim , T. J. ; Shim , S. C. Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: Modified Friedlaender quinoline synthesis . Chem. Commun. 2001 , 24 , 2576 – 2577 .
  • McNaughton , B. R. ; Miller , B. L. A mild and efficient one-step synthesis of quinolines . Org. Lett. 2003 , 5 , 4257 – 4259 .
  • Ranu , B. C. ; Hajra , A. ; Dey , S. S. ; Jana , U. Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions . Tetrahedron 2003 , 59 , 813 – 819 .
  • Cho , C. S. ; Kim , B. T. ; Choi , H. J. ; Kim , T. J. ; Shim , S. C. Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines . Tetrahedron 2003 , 59 , 7997 – 8002 .
  • Motokura , K. ; Mizugaki , T. ; Ebitaniu , K. ; Kaneda , K. Multifunctional catalysis of a ruthenium-grafted hydrotalcite: One-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds via aerobic oxidation and aldol reaction . Tetrahedron Lett. 2004 , 45 , 6029 – 6032 .
  • Friedländer , P. Über o-Amidobenzaldehyd . Chem. Ber. 1882 , 15 , 2572 – 2575 .
  • Song , S. J. ; Cho , S. J. ; Park , D. K. ; Kwon , T. W. ; Jenekhe , S. A. Microwave enhanced solvent-free synthesis of a library of quinoline derivatives . Tetrahedron Lett. 2003 , 44 , 255 – 257 .
  • Haudhuri , M. K. ; Sahid , H. An efficient synthesis of quinolines under solvent-free conditions . J. Chem. Sci. 2006 , 118 , 199 – 202 .
  • Jia , C. S. ; Zhang , Z. ; Tu , S. J. ; Wang , G. W. Rapid and efficient synthesis of poly-substituted quinolines assisted by p-toluene sulphonic acid under solvent-free conditions: Comparative study of microwave irradiation versus conventional heating . Org. Biomol. Chem. 2006 , 4 , 104 – 110 .
  • Mogilaiah , K. ; Rama Sudhakar , G. PTSA-catalyzed Friedlander condensation in the solid state . Indian J. Chem. Sect. B 2003 , 42 , 1170 – 1171 .
  • Wu , J. ; Xia , H. G. ; Gao , K. Molecular iodine: A highly efficient catalyst in the synthesis of quinolines via Friedlander annulation . Org. Biomol. Chem. 2006 , 4 , 126 – 129 .
  • Varala , R. ; Enugala , R. ; Adapa , S. R. Efficient and rapid Friedlander synthesis of functionalized quinolines catalyzed by neodymium(III) nitrate hexahydrate . Synthesis 2006 , 22 , 3825 – 3830 .
  • Dormer , P. G. ; Eng , K. K. ; Farr , R. N. ; Humphrey , G. H. ; McWilliams , J. C. ; Reider , P. J. ; Sager , J. W. ; Volante , R. P. Highly regioselective Friedlander annulations with unmodified ketones employing novel amine catalysts: Syntheses of 2-substituted quinolines, 1,8-naphthyridines, and related heterocycles . J. Org. Chem. 2003 , 68 , 467 – 477 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Sreedhar , P. ; Rao , R. S. ; Nagaiah , K. Silver phosphotungstate: A novel and recyclable heteropoly acid for Friedlander quinoline synthesis . Synthesis 2004 , 14 , 2381 – 2385 .
  • Zhang , L. ; Wua , J. Friedlaender synthesis of quinolines using a lewis acid–surfactant combined catalyst in water . Adv. Synth. Catal. 2007 , 349 , 1047 – 1051 .
  • Wang , G. W. ; Jia , C. S. ; Dong , Y. W. Benign and highly efficient synthesis of quinolines from 2-aminoarylketone or 2-aminoarylaldehyde and carbonyl compounds mediated by hydrochloric acid in water . Tetrahedron Lett. 2006 , 47 , 1059 – 1063 .
  • Das , B. ; Damodar , K. ; Chowdhury , N. ; Kumar , R. A. Application of heterogeneous solid acid catalysts for Friedlander synthesis of quinolines . J. Mol. Catal. A. Chem. 2007 , 274 , 148 – 152 .
  • Narasimhulu , M. ; Reddy , T. S. ; Mahesh , K. C. ; Prabhakar , P. ; Rao , C. B. ; Venkateswarlu , Y. Silica supported perchloric acid: A mild and highly efficient heterogeneous catalyst for the synthesis of poly-substituted quinolines via Friedlander hetero-annulation . J. Mol. Catal. A: Chem. 2007 , 266 , 114 – 117 .
  • Clark , J. H. Solid acids for green chemistry. Acc. Chem. Res. 2002, 35, 791–797.
  • Curini , M. ; Rosati , O. ; Campagna , V. ; Montanari , F. ; Cravotto , G. ; Boccalini , M. Layered zirconium sulfophenyl phosphonate as heterogeneous catalyst in the synthesis of pyrazoles and 4,5,6,7-tetrahydro-1(2)H-indazoles . Synlett 2005 , 19 , 2927 – 2930 .
  • Upadhyaya , D. J. ; Barge , A. ; Stefania , R. ; Cravotto , G. Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst . Tetrahedron Lett. 2007 , 48 , 8318 – 8322 .
  • Cravotto , G. ; Mendicuti , F. ; Martina , K. ; Tagliapietra , S. ; Robaldo , B. ; Barge , A. A new access to homo- and heterodimers of α-, β-, and γ-cyclodextrin by a microwave-promoted huisgen cycloaddition . Synlett 2008 , 18 , 2642 – 2646 .
  • Karimi , B. ; Khalkhali , M. Solid silica-based sulfonic acid as an efficient and recoverable interphase catalyst for selective tetrahydropyranylation of alcohols and phenols . J. Mol. Catal. A: Chem. 2005 , 232 , 113 – 117 .
  • Karimi , B. ; Khalkhali , M. Silica functionalized sulfonic acid as a recyclable interphase catalyst for chemoselective thioacetalization of carbonyl compounds in water . J. Mol. Catal. A: Chem. 2007 , 271 , 75 – 79 .
  • Herrero , M. A. ; Kremsner , J. M. ; Kappe , C. O. Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry . J. Org. Chem. 2008 , 73 , 36 – 47 .
  • Palimkar , S. S. ; Siddiqui , S. A. ; Rajgopal , T. D. ; Lahoti , J. ; Srinivasan , K. V. Ionic liquid–promoted regiospecific Friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines . J. Org. Chem. 2003 , 68 , 9371 – 9378 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Premalatha , K. Bi(OTf)(3)-catalyzed Friedlander hetero-annulation: A rapid synthesis of 2,3,4-trisubstituted quinolines . Synlett 2004 , 6 , 963 – 966 .
  • Shaabani , A. ; Soleimani , E. ; Badri , Z. Silica sulfuric acid as an inexpensive and recyclable solid acid catalyzed efficient synthesis of quinolines . Monatsh. Chem. 2006 , 137 , 181 – 184 .
  • Varala , R. ; Enugala , R. ; Adapa , S. R. Efficient and rapid Friedlander synthesis of functionalized quinolines catalyzed by neodymium(III) nitrate hexahydrate . Synthesis 2006 , 22 , 3825 – 3830 .
  • Yadav , J. S. ; Purushothama Rao , P. ; Sreenu , D. ; Srinivasa Rao , R. ; Naveen Kumar , K. ; Prasad , A. R. Sulfamic acid: An efficient, cost-effective, and recyclable solid acid catalyst for the Friedlander quinoline synthesis . Tetrahedron Lett. 2005 , 46 , 7249 – 7253 .
  • Bose , D. S. ; Kumar , R. K. High-yielding microwave assisted synthesis of quinoline and dihydroquinoline derivatives under solvent-free conditions . Heterocycles 2006 , 68 , 549 – 559 .

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