Synthesis of novel tryptamine and azepinoindole derivatives

Heterocycles

Volumn 45, Issue 12, 1997, Pages 2331-2347

  Novák, Lajos ^a   Hanania, Michel ^a   Kovács, Péter ^b   Rohály, János ^a   Kolonits, Pál ^a   Szántay, Csaba ^a,b  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b CTRL RES INSTITUTE FOR CHEMISTRY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001385870     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-97-7918     Document Type: Article

References (12)

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3. M. Iwao and F. Ishibashi, Tetrahedron, 1997, 53, 51, and references cited therein.
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9. L. Szabó, L. Dobay, Gy. Kalaus, E. Gács-Baitz, J, Tamás, and Cs. Szántay, Arch.Pharm., 1987, 320, 781.
10. R.P. Phillips; The Japp-Klingemann Reaction. Org. React., 10, John Wiley, New York, 1959, p. 143.
11. In the intermediate (6a) three nucleophilic centers (C-2, C-3, and C-4) should be taken into consideration. Position 2 is occupied by ethoxycarbonyl group preventing this position from reacting with the iminium system. Earlier investigation with indole derivatives has indicated that direct electrophilic substitution at the benzene ring was unfavorable compared with attack at position 3, and the formed indolenine readily rearranged to 2,3-disubstituted indole derivative. A.H. Jackson and A.E. Smith, Tetrahedron, 1968, 24, 403.
12. A.H. Jackson, B. Naidoo, and P. Smith, Tetrahedron, 1968, 24, 6119.