Convenient Synthesis of 5,6,7,8-Tetrahydroquinolin-8-ylamine and 6,7-Dihydro-5H-quinolin-8-one

References

• Bridger , G. , Skerlj , R. , Kaller , A. , Harwig , C. , Bogucki , D. , Wilson , T.R. , Crawford , J. , McEachern , E.J. , Atsma , B. , Nan , S. , Zhou , Y. , Schols , D. , Smith , C.D. and Di Fluri , R.M. 2002 . Preparation of Tertiary N-(5,6,7,8-Tetrahydro-8-quinolinyl)-N-(1H-benzimidazol-2-ylmethyl)amines and analogs as chemokine receptor modulators for treatment of HIV or FIV . PCT Int. Appl. WO 0234745 ,
   Google Scholar
• Yu , G. , Macor , J. , Herpin , T. , Lawrence , R.M. , Morton , G.C. , Ruel , R. , Poindexter , G.S. , Ruediger , E.H. and Thibault , C. 2002 . Preparation of peptides for pharmaceutical use as modulators of melanocortin receptors . PCT Int. Appl. WO 0270511 ,
   Google Scholar
• Tobe , T. , Sugane , T. , Hamaguchi , W. , Shimada , I. , Maeno , K. , Miyata , J. , Kimizuka , T. , Suzuki , T. , Kohara , A. , Morita , T. , Arlt , M. and Greiner , H. 2001 . Preparation of triazole derivatives as glycine transporter inhibitors useful as learning improving agents . PCT Int. Appl. WO 0187855 ,
   Google Scholar
• Yamazaki , T. , Maruoka , H. , Suzuki , S. , Mukade , T. , Hirose , K. , Yanaka , M. and Yamamoto , N. 2001 . Preparation of amino acid amide and dipeptide derivatives and antiviral drugs containing the same . PCT Int. Appl. WO 0179168 ,
   Google Scholar
• Kees , K.L. , Smith , T.M. , McCaleb , M.L. , Prozialeck , D.H. , Cheeseman , R.S. , Christos , T.E. , Patt , W.C. and Steiner , K.E. 1992 . Perfluorocarbon-based antidiabetic agents . J. Med. Chem. , 35 : 944 – 953 .
   PubMed Web of Science ®Google Scholar
• Beattie , D.E. , Crossley , R. , Curran , A.C.W. , Hill , D.G. and Lawrence , A.E. 1977 . 5,6,7,8-Tetrahydroquinolines. 5. Antiulcer and antisecretory activity of 5,6,7,8-tetrahydroquinolinethioureas and related heterocycles . J. Med. Chem. , 20 : 718 – 721 .
   PubMed Web of Science ®Google Scholar
• Beschke , H. 1978 . Chemical reactions of 2,3-cycloalkenopyridines . Aldrichimica Acta , 11 : 13 – 16 .
   Google Scholar
• Uenishi , J. and Hamada , M. 2002 . A similar synthesis of 3 has recently been reported. Synthesis of enantiomerically pure 8-substituted 5,6,7,8-tetrahydro quinolines . Synthesis , 5 : 625 – 630 .
   Google Scholar
• Skupinska , K.A. , McEachern , E.J. , Skerlj , R.T. and Bridger , G.J. 2002 . Compound 3 has also been prepared by selective hydrogenation of 8-acetamidoquinoline. Concise preparation of amino-5,6,7,8-tetrahydroquinolines and amino-5,6,7,8-tetrahydroisoquinolines via catalytic hydrogenation of acetamidoquinolines and acetamidoiso-quinolines . J. Org. Chem. , 67 : 7890 – 7893 .
   PubMed Web of Science ®Google Scholar
• Tagawa , Y. , Arakawa , H. and Goto , Y. 1989 . Nitrosation of 1-alkylisoquinolines and their N-oxides and configurational assignments of their oximes . Heterocycles , 29 : 1741 – 1760 .
   Web of Science ®Google Scholar
• Lardenois , P. , Frost , J. , Dargazanli , G. and George , P. 1996 . A convenient synthesis of 7,8-dihydroisoquinolin-5(6H)-one . Synth. Commun. , 26 : 2305 – 2308 .
   Web of Science ®Google Scholar
• Jochims , J.C. 1963 . Reduktion von ketoximen mit zinkstaub in ammoniakalischer losung . Monatsh. Chem. , 94 : 677 – 680 .
   Web of Science ®Google Scholar
• Thummel , R.P. , Lefoulon , F. , Cantu , D. and Mahadevan , R. 1984 . Polyaza cavity-shaped molecules— annelated derivatives of 2-(2′-pyridyl)-1,8-naphthyridine and 2,2′-bi-1,8-naphthyridine . J. Org. Chem. , 49 : 2208 – 2212 . For an alternative synthesis of 7 see:
   Web of Science ®Google Scholar