117
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Polycyclic-fused Heterocycles Combining Both Quinoline Ring and Benzoxepine Framework in A Single Molecule

, &
Pages 469-486 | Received 16 Oct 2011, Accepted 26 Jan 2012, Published online: 14 Sep 2012

REFERENCES

  • Beauchard , A. , Jaunet , A. , Murillo , L. , Baldeyrou , B. , Lansiaux , A. , Chérouvrier , J. R. , Domon , L. , Picot , L. , Bailly , C. , Besson , T. and Thiéry , V. 2009 . Synthesis and Antitumoral Activity of Novel Thiazolobenzotriazole, Thiazoloindolo[3,2-c]quinoline and Quinolino Quinoline Derivatives . Eur. J. Med. Chem. , 44 : 3858 – 65 .
  • Yang , S. W. , Abdel-Kader , M. , Malone , S. , Werkhoven , M. C. M. , Wisse , J. H. , Bursuker , I. , Neddermann , K. , Fairchild , C. , Raventos-Suarez , C. , Menendez , A. T. , Lane , K. and Kingston , D. G. I. 1999 . Synthesis and Biological Evaluation of Analogues of Cryptolepine, an Alkaloid Isolated from the Suriname Rainforest . J. Nat. Prod. , 62 : 976 – 83 .
  • Miert , S. V. , Miert , S. V. , Hostyn , S. , Maes , B. U. W. , Cimanga , K. , Brun , R. , Kaiser , M. , Mátyus , P. , Dommisse , R. , Lemière , G. , Vlietinck , A. and Pieters , L. 2005 . Isoneocryptolepine, a Synthetic Indoloquinoline Alkaloid, as an Antiplasmodial Lead Compound . J. Nat. Prod. , 68 : 674 – 7 .
  • Eswaran , S. , Adhikari , A. V. and Kumar , R. A. 2010 . New 1,3-Oxazolo[4,5-c]quinoline Derivatives: Synthesis and Evaluation of Antibacterial and Antituberculosis Properties . Eur. J. Med. Chem. , 45 : 957 – 66 .
  • Yang , C. L. , Tseng , C. H. , Chen , Y. L. , Lu , C. M. , Kao , C. L. , Wu , M. H. and Tzeng , C. C. 2010 . Identification of Benzofuro[2,3-b]quinoline Derivatives as a New Class of Antituberculosis Agents . Eur. J. Med. Chem. , 45 : 602 – 7 .
  • Rossi , E. , Abbiati , G. , Arcadi , A. and Marinelli , F. 2001 . Concise Synthesis of Fused Polycyclic Quinolines . Tetrahedron Lett. , 42 : 3705 – 8 .
  • Kalita , P. K. , Baruah , B. and Bhuyan , P. J. 2006 . Synthesis of Novel Pyrano[2,3-b]quinolines from Simple Acetanilides via Intramolecular 1,3-dipolar Cycloaddition . Tetrahedron Lett. , 47 : 7779 – 82 .
  • Mali , J. R. , Pratap , U. R. , Jawale , D. V. and Mane , R. A. 2010 . Water-mediated One-pot Synthetic Route for Pyrazolo[3,4-b]quinolines . Tetrahedron Lett. , 51 : 3980 – 2 .
  • Malecki , N. , Carato , P. , Rigo , B. , Goossens , J. F. , Houssin , R. , Bailly , C. and Hénichart , J. P. 2004 . Synthesis of Condensed Quinolines and Quinazolines as DNA Ligands . Bioorg. Med. Chem. , 12 : 641 – 7 .
  • Venkataraman , S. , Barange , D. K. and Pal , M. 2006 . One-pot Synthesis of 2-Substituted furo[3,2-c]quinolines via Tandem Coupling–cyclization under Pd/C-copper Catalysis . Tetrahedron Lett. , 47 : 7317 – 22 .
  • Khorshidi , A. and Tabatabaeian , K. 2011 . Ruthenium-exchanged FAU-Y Zeolite Catalyzed Improvement in the Synthesis of 6H-indolo[2,3-b]quinolines . J. Mol. Cataly. A: Chem. , 344 : 128 – 31 .
  • Boateng , C. A. , Eyunni , S. V. K. , Zhu , X. Y. , Etukala , J. R. , Bricker , B. A. , Ashfaq , M. K. , Jacob , M. R. , Khan , S. I. , Walker , L. A. and Ablordeppey , S. Y. 2011 . Benzothieno[3,2-b]quinolinium and 3-(phenylthio)quinolinium Compounds: Synthesis and Evaluation against Opportunistic Fungal Pathogens . Bioorg. Med. Chem. , 19 : 458 – 70 .
  • Bera , R. , Dhananjaya , G. , Singh , S. N. , Ramu , B. , Kiran , S. U. , Kumar , P. R. , Mukkanti , K. and Pal , M. 2008 . Revisiting the Reaction of β-chloroacroleins with 2-aminophenol: A New Observation . Tetrahedron , 64 : 582 – 9 .
  • Roy , A. , Biswas , B. , Sen , P. K. and Venkateswaran , R. V. 2007 . Total Synthesis of Heliannuol B, an Allelochemical from Helianthus Annuus . Tetrahedron Lett. , 48 : 6933 – 6 .
  • Gruijters , B. W. T. , van Veldhuizen , A. , Weijers , C. A. G. M. and Wijnberg , J. B. P. A. 2002 . Total Synthesis and Bioactivity of Some Naturally Occurring Pterulones . J. Nat. Prod. , 65 : 558 – 61 .
  • Pettit , G. R. , Numata , A. , Iwamoto , C. , Usami , Y. , Yamada , T. , Ohishi , H. and Cragg , G. M. 2006 . Antineoplastic Agents. 551. Isolation and Structures of Bauhiniastatins 1−4 from Bauhinia purpurea . J. Nat. Prod. , 69 : 323 – 7 .
  • Yoshida , M. , Nakatani , K. and Shishido , K. 2009 . Total Synthesis of Radulanin H and Proposed Structure of Radulanin E . Tetrahedron , 65 : 5702 – 8 .
  • Bruder , M. , Haseler , P. L. , Muscarella , M. , Lewis , W. and Moody , C. J. 2010 . Synthesis of the Oxepinochromone Natural Products Ptaeroxylin (Desoxykarenin), Ptaeroxylinol, and Eranthin . J. Org. Chem. , 75 : 353 – 8 .
  • Kahnberg , P. and Sterner , O. 2001 . Synthesis of the Antifungal 1-Benzoxepin Pterulone . Tetrahedron , 57 : 7181 – 4 .
  • Staben , S. T. , Siu , M. , Goldsmith , R. , Olivero , A. G. , Do , S. , Burdick , D. J. , Heffron , T. P. , Dotson , J. , Sutherlin , D. P. , Zhu , B. Y. , Tsui , V. , Le , H. , Lee , L. , Lesnick , J. , Lewis , C. , Murray , J. M. , Nonomiya , J. , Pang , J. , Prior , W. W. , Salphati , L. , Rouge , L. , Sampath , D. , Sideris , S. , Wiesmann , C. and Wu , P. 2011 . Structure-based Design of Thienobenzoxepin Inhibitors of PI3-Kinase . Bioorg. Med. Chem. Lett. , 21 : 4054 – 8 .
  • Liu , J. H. , Steigel , A. , Reininger , E. and Bauer , R. 2000 . Two New Prenylated 3-Benzoxepin Derivatives as Cyclooxygenase Inhibitors from Perilla frutescens var. Acuta . J. Nat. Prod. , 63 : 403 – 5 .
  • Lautens , M. , Paquin , J. F. and Piguel , S. 2002 . Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions. Application to the Synthesis of 2-Substituted-4-Benzoxepines and 2,5-Disubstituted-4-Benzoxepines . J. Org. Chem. , 67 : 3972 – 4 .
  • Kahnberg , P. , Lee , C. W. , Grubbs , R. H and Sterner , O. 2002 . Alternative Routes to Pterulone . Tetrahedron , 58 : 5203 – 8 .
  • Arnold , L. A. , Luo , W. and Guy , R. K. 2004 . Synthesis of Medium Ring Heterocycles Using an Intramolecular Heck Reaction . Org. Lett. , 6 : 3005 – 7 .
  • Rotzoll , S. , Appel , B. and Langer , P. 2005 . Synthesis of 2,3-Benzoxepins by Sequential Cyclopropanation/Ring-Enlargement Reactions of Benzopyrylium Triflates with Diazoesters . Tetrahedron Lett. , 46 : 4057 – 9 .
  • Barrett , I. , Meegan , M. J. , Hughes , R. B. , Carr , M. , Knox , A. J. S. , Artemenko , N. , Golfis , G. , Zisterer , D. M. and Lloyd , D. G. 2008 . Synthesis, Biological Evaluation, Structural–Activity Relationship, and Docking Study for a Series Of Benzoxepin-Derived Estrogen Receptor Modulators . Bioorg. Med. Chem. , 16 : 9554 – 73 .
  • Roux , L. , Charrier , C. , Salomon , E. , Ilhan , M. , Bisseret , P. and Tarnus , C. 2011 . An Innovative Strategy for the Synthesis of a New Series of Potentaminopeptidase (APN or CD13) Inhibitors Derived from the Oxepin-4-One Family . Tetrahedron Lett. , 52 : 2586 – 9 .
  • Kumar , S. , Il , H. and Junjapp , H. 2007 . Heteroaromatic Annulation Studies on 10,11-dihydro-11-[bis(methylthio)methylene]dibenzoxepin-10-one: A Facile Access to Novel dibenzoxepino[4,5]-fused Heterocycles . Tetrahedron , 63 : 10067 – 76 .
  • Dolle , R. E. and Nelson , K. H. Jr. 1998, 1999 . Comprehensive Survey of Combinatorial Library Synthesis: . J. Comb. Chem. , 1 : 235 – 82 .
  • Gao , W. T. , Zhang , X. F. , Li , Y. , Liu , H. Y. and Imafuku , K. 2010 . First Synthesis of 2-Tropolonylquinoline-4-carboxylic Acid Derivatives via Pfitzinger Reaction in Water . Heterocycles , 81 : 1689 – 96 .
  • Gao , W. T. , Liu , J. , Jiang , Y. and Li , Y. 2011 . First Synthesis of 2-(Benzofuran-2-yl)-6,7-Methylenedioxyquinoline-3-carboxylic Acid Derivatives . Beilstein J. Org. Chem. , 7 : 210 – 7 .
  • Cui , D. M. , Kawamura , M. , Shimada , S. , Hayashi , T. and Tanaka , M. 2003 . Synthesis of 1-tetralones by Intramolecular Friedel–Crafts Reaction of 4-arylbutyric Acids using Lewis Acid Catalysts . Tetrahedron Lett. , 44 : 4007 – 10 .
  • Jagtap , P. G. , Chen , Z. and Southan , G. J. 2009 . Chlorosulfonic Acid-Mediated Cyclization of 4-Phenyl-3-isocoumarincarboxylic acids and 4-phenyl-3-isoquinolinonecarboxylic Acids: An Efficient Synthesis of 3-oxoindeno[2,1-c]isocoumarins and 3-oxoindeno[2,1-c]isoquinolinones . Tetrahedron Lett. , 50 : 2057 – 9 .
  • Tseng , C. H. , Chen , Y. L. , Chung , K. Y. , Cheng , C. M. and Wang , C. H. 2009 . Synthesis and Antiproliferative Evaluation of 6-arylindeno[1,2-c]quinoline Derivatives . Bioorg. Med. Chem. , 17 : 7465 – 76 .
  • Zhong , W. , Ma , W. and Liu , Y. 2011 . First Construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8]thiocino-[2,3-b]quinolines via Intramolecular Friedel–Crafts Reaction of Morita–Baylis– Hillman Adducts . Tetrahedron , 67 : 3509 – 18 .
  • Chujo , I. , Masuda , Y. , Fujino , K. , Kato , S. , Ogasa , T. , Mohri , S. and Kasai , M. 2001 . Synthetic Study on Novel Immunosuppressant KF20444 . Bioorg. Med. Chem. , 9 : 3273 – 86 .
  • Kaufmann , D. , Fünfschilling , P. C. , Beutler , U. , Hoehn , P. , Lohse , O. and Zaugg , W. 2004 . A New Synthesis of Oxcarbazepine using a Friedel–Crafts Cyclization Strategy . Tetrahedron Lett. , 45 : 5275 – 78 .
  • Nacro , K. , Zha , C. , Guzzo , P. R. , Herr , R. J. , Peace , D. and Friedrich , T. D. 2007 . Synthesis and Topoisomerase Poisoning Activity of A-ring and E-ring Substituted Luotonin A Derivatives . Bioorg. Med. Chem. , 15 : 4237 – 46 .
  • Kalkhambkar , R. G. , Kulkarni , G. M. , Shivkumar , H. and Rao , R. N. 2007 . Synthesis of Novel Triheterocyclic Thiazoles as Anti-Inflammatory and Analgesic Agents . Eur. J. Med. Chem. , 42 : 1272 – 6 .
  • Muscia , G. C. , Cazorla , S. I. , Frank , F. M. , Borosky , G. L. , Buldain , G. Y. , Asís , S. E. and Malchiodi , E. L. 2011 . Synthesis, Trypanocidal Activity and Molecular Modeling Studies of 2-alkylaminomethylquinoline Derivatives . Eur. J. Med. Chem. , 46 : 3696 – 3703 .
  • Muscia , G. C. , Bollini , M. , Carnevale , J. P. , Bruno , A. M. and Asís , S. E. 2006 . Microwave-assisted Friedländer Synthesis of Quinolines Derivatives as Potential Antiparasitic Agents . Tetrahedron Lett. , 47 : 8811 – 15 .
  • Adams , D. R. and de Saizarbitoria , T. C. 1987 . A ‘One-Pot’ Synthesis of Substituted 3-Carboethoxy-2-methylquinolines from Ethyl Acetoacetate . Synth. Commun. , 17 : 1647 – 53 .
  • Zarghi , A. and Ghodsi , R. 2010 . Design, Synthesis, and Biological Evaluation of Ketoprofen Analogs as Potent Cyclooxygenase-2 Inhibitors . Bioorg. Med. Chem. , 18 : 5855 – 60 .
  • Irlapati , N. R. , Baldwin , J. E. , Adlington , R. M. , Pritchard , G. J. and Cowley , A. R. 2006 . Studies towards the Biomimetic Synthesis of Pyridomacrolidin . Tetrahedron , 62 : 4603 – 14 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.