1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and este

Details 1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and este 1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and este

1975-06-23

1976-12-14

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424258, C07D21508

Patent

active

039975428

ABSTRACT:
Compounds useful as antiamebic agents are 1-(Ac.sub.1)-5-R-6-(Ac.sub.2 O)-1,2,3,4-tetrahydroquinolines (I), where Ac.sub.1 is haloacetyl, dihaloacetyl or trihaloacetyl with halo being chloro or bromo, R is hydrogen, chloro or bromo, and Ac.sub.2 is hydrogen, Ac.sub.1, alkanoyl having from one to sixteen carbon atoms, benzoyl, 2(or 3)-thenoyl, 2(or 3)-furoyl or N-(lower-alkyl)carbamoyl. Said compounds are prepared: by reacting 1,2,3,4-tetrahydro-6-quinolinol with an acyl halide of the formula Ac.sub.1 -halogen to produce 1-(Ac.sub.1)-1,2,3,4-tetrahydro-6-quinolinol having formula I where R and Ac.sub.2 are each hydrogen, Ac.sub.1 is defined as in formula I and halide is chloride or bromide; by reacting said 1-(Ac.sub.1)-1,2,3,4-tetrahydro-6-quinolinol with a chlorinating or brominating agent to produce the corresponding 1-(Ac.sub.1)-5-chloro(or bromo)-1,2,3,4-tetrahydro-6-quinolinol where Ac.sub.1 is defined as in claim 1; and, by reacting 1-(Ac.sub.1)-5-R-1,2,3,4-tetrahydro-6-quinolinol with an acylating agent providing Ac.sub.2 to produce 1-(Ac.sub.1)-5-R-1,2,3,4-tetrahydro-6-(Ac.sub.2 O)quinoline having formula I where R is hydrogen, chloro or bromo, Ac.sub.1 is defined as in formula I and Ac.sub.2 is other than hydrogen as defined in formula I.

REFERENCES:
patent: 2666058 (1950-05-01), Neher
patent: 3793314 (1974-02-01), Nardi et al.
Nagarajan, "Indian J. Chem.," 1969, pp. 848, 852-857.
Svensson et al. "Tetrahedron" 29, 1973, p. 1115ff.
March, "Advanced Organic Chemistry," 1968, pp. 319-320.
House, "Modern Synthetic Reactions," pp. 268, 274 (1965).

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