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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
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Original Articles

Simple and Convenient Approach for Synthesis of Tetrahydroquinoline Derivatives and Studies on Aza-Cope Rearrangement

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Pages 1809-1828 | Received 25 Jan 2010, Published online: 29 Apr 2011

REFERENCES

  • (a) Shen , L. ; Ye , Y.-H. ; Wang , X.-T. ; Zhu , H.-L. ; Xu , C. ; Song , Y.-C. ; Hai Li , H. ; Tan , R.-X. Structure and total synthesis of aspernigerin: A novel cytotoxic endophyte metabolite . Chem. Eur. J. 2006 , 12 , 4393 – 4396 ; (b) Itou , Y. ; Okada , S. ; Murakami , M. Two structural isomeric siderophores from the freshwater cyanobacterium Anabaena cylindrica (NIES-19) . Tetrahedron 2001 , 57 , 9093 – 9099 .
  • Bendale , P. ; Olepu , S. ; Suryadevara , P. K. ; Bulbule , V. ; Rivas , K. ; Nallan , L. ; Smart , B. ; Yokoyama , K. ; Ankala , S. ; Pendyala , P. R. ; Floyd , D. ; Lombardo , L. J. ; Williams , D. K. ; Buckner , F. S. ; Chakrabarti , D. ; Verlinde , C. L. M. J. ; Voorhis , W. C. V. ; Gelb , M. H. Second-generation tetrahydroquinoline-based protein farnesyltransferase inhibitors as antimalarials. J. Med. Chem. 2007, 50, 4585–4605.
  • Rochus , J. ; Ingeborg , L. ; Norbest , B. ; Michacl , K. ; Otta , M. K. Preparation of [(benzimidoyl)tetrahydroquinolinyl]dihydrothiadiazinones as cardiovascular agents . Ger. Patent 4141074 , 1992 .
  • Otta , G. ; Thomas , R. ; Rudi , B. ; Josef , S. ; Eberhard , N. R. Tetrahydroquinoline derivatives for pharmaceutical compositions . Ger. Patent 2934609 , 1984 .
  • Brundish , D. ; Bull , A. ; Donovan , V. ; Fullerton , J. D. ; Garman , S. M. ; Hayler , J. F. ; Janus , D. ; Kane , P. D. ; McDonnell , M. ; Smith , G. P. ; Wakeford , R. ; Walker , C. V. ; Howarth , G. ; Hoyle , W. ; Allen , M. C. ; Ambler , J. ; Butler , K. ; Mark , D. ; Talbot , M. D. Design and synthesis of thrombin inhibitors: Analogues of MD-805 with reduced stereogenicity and improved potency . J. Med. Chem. 1999 , 42 , 4584 – 4603 .
  • Hiessbock , R. ; Wolf , C. ; Richter , E. ; Hitzler , M. ; Chiba , P. ; Kratzel , M. ; Ecker , G. Synthesis and in vitro multidrug resistance modulating activity of a series of dihydrobenzopyrans and tetrahydroquinolines . J. Med. Chem. 1999 , 42 , 1921 – 1926 .
  • Westaway , S. M. ; Chung , Y.-K. ; Davis , J. B. ; Holland , V. ; Jerman , J. C. ; Medhurst , S. J. ; Rami , H. K. ; Stemp , G. ; Stevens , A. J. ; Thompson , M. ; Winbron , K. M. ; Wright , J. N-Tetrahydroquinolinyl, N-quinolinyl, and N-isoquinolinyl biaryl carboxamides as antagonists of TRPV1 . Bioorg. Med. Chem. Lett. 2006 , 16 , 4533 – 4536 .
  • (a) Rapoport , H. ; Tretter , J. R. Six-membered ring formation during Fischer indole synthesis . J. Am. Chem. Soc. 1958 , 80 , 5574 – 5575 ; (b) Bass , R. J. ; Koch , R. C. ; Richards , H. C. ; Thorpe , J. E. Tricyclic amides: A new class of systemic fungicides active against rice blast disease . J. Agric. Food. Chem. 1981 , 29 , 576 – 579 .
  • (a) Abonia , R. ; Albornza , A. ; Insuaty , B. ; Quiroga , J. ; Meier , H. ; Homaza , A. ; Nogueras , M. ; Sanchez , A. ; Cobo , J. ; Low , J. Synthesis of novel 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolines via benzotriazole methodology . Tetrahedron 2001 , 57 , 4933 – 4938 ; (b) Glass , D. B. ; Weissberger , A. Julolidine . Org. Synth. 1946 , 26 , 40 – 41 ; (c) Katayama , H. ; Abe , E. ; Kaneko , K. Synthesis of julolidines from anilines . J. Heterocycl. Chem. 1982 , 19 , 925 – 926 ; (d) Shono , T. ; Matsumura , Y. ; Ious , K. ; Ohmizu , H. ; Kashimura , S. Electroorganic chemistry, 62: Reaction of iminium ion with nucleophile: A versatile synthesis of tetrahydroquinolines and julolidines . J. Am. Chem. Soc. 1982 , 104 , 5753 – 5757 .
  • Mahuzier , G. ; Chalom , J. ; Farinotti , R. ; Tod , M. New derivatives of tetrahydro-2,3,6,7,11H-(1) benzopyrano(6,7,8,ij)quinolizone-11 usable as markers for organic compounds for the purpose of detecting said compounds by chemiluminescence or fluorescence . WO Patient 89/12052 , 1989 .
  • Titus , J. A. ; Haugland , R. ; Sharrow , S. O. ; Segal , D. M. Texas red, a hydrophilic, red-emitting flourophore for use with flourescein in dual parameter flow microfluorometric and fluorescence microscopic studies . J. Immunol. Methods. 1982 , 51 , 193 – 204 .
  • Reynolds , G. A. Pyrylium dyes having a fused, rigidized nitrogen-containing ring . U.S. Patent 4005092 , 1977 .
  • (a) Nose , A. ; Kudo , T. Reduction of heterocyclic compounds, II: Reduction of heterocyclic compounds with sodium borohydride–transition metal salt systems . Chem. Pharm. Bull. 1984 , 32 , 2421 – 2425 ; (b) Nose , A. ; Kudo , T. Studies of reduction of various organic compounds with the nickel(II) chloride–zinc system . Chem. Pharm. Bull. 1990 , 38 , 2097 – 2101 ; (c) Fujita , K.-I. ; Kitatsuji , C. ; Furukawa , S. ; Yamaguchi , R. Regio- and chemoselective transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex . Tetrahedron Lett. 2004 , 42 , 3215 – 3217 .
  • Johnson , W. S. ; Buell , B. G. 1, 2-Dihydroquinoline. J. Am. Chem. Soc. 1952, 74, 4517–4520.
  • Perold , G. W. ; Reiche , V. K. V. The chemistry of the 2-isoxazolines: Reductive cleavages . J. Am. Chem. Soc. 1957 , 79 , 465 – 467 .
  • Bringi , N. V. ; Deshmukh , P. V. Hydroxy alkylation of primary aromatic amines . J. Org. Chem. 1962 , 27 , 4117 – 4118 .
  • (a) Walser , A. ; Zenchoff , G. ; Fryer , R. I. 1,2,3,4-Tetrahydroquinolines and 1,2-dihydroquinolines from 2-aminobenzophenes . J. Heterocycl. Chem. 1976 , 13 , 131 – 133 ; (b) Makino , K. ; Hara , O. ; Takiguchi , Y. ; Katano , R. ; Asakawa , Y. ; Hatano , K. ; Hamada , Y. Efficient construction of 1,2-dihydroquinoline and 1,2,3,4-tetrahydroquinoline rings using tandem Michael–aldol reaction . Tetrahedron Lett. 2003 , 44 , 8925 – 8929 .
  • Beifuss , U. ; Ledderhose , S. Intermolecular polar [4π + + 2 π] cycloadditions of cationic 2-azabutadienes from thiomethylamines: A new and efficient method for the regio- and diastereoselective synthesis of 1,2,3,4-tetrahydroquinolines . J. Chem. Soc., Chem. Commun . 1995 , 2137 – 2138 .
  • (a) Katritzky , A. R. ; Gordeev , M. F. Lithium tetrafluoroborate–assisted reactions of N-(α-aminoalkyl)benzotriazoles with olefins and 1,3-dienes: New syntheses of 1,2,5,6-tetrahydropyridinium salts, 1,2,3,4-tetrahydroquinolines, and some related heterocyclic systems . J. Org. Chem. 1993 , 58 , 4049 – 4053 ; (b) Katritzky , A. R. ; Reachwal , B. ; Rachwal , S. A. Versatile method for the preparation of substituted 1,2,3,4-tetrahydroquinolines . J. Org. Chem. 1995 , 60 , 7631 – 7640 .
  • Kuznetsov , V. V. ; Aliev , A. E. ; Prostakov , N. S. Synthesis of 2-alkyl(aryl, hetaryl)-4-methyl-1,2,3,4-tetrahydroquinolines . Chem. Heterocycl. Comp. 1994 , 30 , 64 – 68 .
  • Meyers , A. I. ; Collington , E. W. Facile and specific conversion of allylic alcohols to allylic chlorides without rearrangement . J. Org. Chem. 1971 , 36 , 3044 – 3045 .
  • Jolidon , S. ; Hansen , H.-J. Untersuchungen über aromatische Amino-Claisen-Umlagerungen . Helv. Chim. Acta. 1977 , 60 , 978 – 1032 .
  • Katayama , H. ; Takatsu , N. Amino-Claisen rearrangement, II: Quaternary amino-Claisen rearrangement of anilinium compounds with ortho substituents . Chem. Pharm. Bull. 1981 , 29 , 2465 – 2477 .
  • Katritzky , A. R. ; Rachwal , B. ; Rachwal , S. Convenient synthesis of julolidines using benzotriazole methodology . J. Org. Chem. 1996 , 61 , 3117 – 3126 .
  • Lutz , R. P. Catalysis of the Cope and Claisen rearrangements . Chem. Rev. 1984 , 84 , 205 – 247 .

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