Convenient synthesis of 5,6,7,8-tetrahydroquinolin-8-ylamine and 6,7-dihydro-5H-quinolin-8-one

Synthetic Communications

Volumn 33, Issue 20, 2003, Pages 3497-3502

  McEachern, E J ^a   Yang, W ^a   Chen, G ^a   Skerlj, R T ^a   Bridger, G J ^a  

^a GENZYME CORPORATION   (United States)

Author keywords

5,6,7,8 Tetrahydroquinoline; Nitrosation; Oxime hydrolysis; Oxime reduction; Substituted pyridines

Indexed keywords

5,6,7,8 TETRAHYDROQUINOLIN 8 YLAMINE; 6,7 DIHYDRO 5H QUINOLIN 8 ONE; OXIME; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; HYDROLYSIS; NITROSATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141865681     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120024729     Document Type: Article

References (13)

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7. Beschke, H. Chemical reactions of 2,3-cycloalkenopyridines. Aldrichimica Acta 1978, 11, 13-16.
8. Uenishi, J.; Hamada, M. A similar synthesis of 3 has recently been reported. Synthesis of enantiomerically pure 8-substituted 5,6,7,8-tetrahydroquinolines. Synthesis 2002, 5, 625-630.
9. Skupinska, K.A.; McEachern, E.J.; Skerlj, R.T.; Bridger, G.J. 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 acetamidoisoquinolines. J. Org. Chem. 2002, 67, 7890-7893.
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13. For an alternative synthesis of 7, see: Thummel, R.P.; Lefoulon, F.; Cantu, D.; Mahadevan, R. Polyaza cavity-shaped molecules-annelated derivatives of 2-(2′-pyridyl)-1,8-naphthyridine and 2,2′-bi-1,8-naphthyridine. J. Org. Chem. 1984, 49, 2208-2212.