Process for preparing cyano derivatives of tetrahydroquinolines

Details Process for preparing cyano derivatives of tetrahydroquinolines Process for preparing cyano derivatives of tetrahydroquinolines

1981-12-02

1985-07-16

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546104, 546108, 546109, 546111, 546173, 546176, 546177, C07D21518, C07D21904, C07D22112, C07D22116

Patent

active

045297983

ABSTRACT:
Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.

REFERENCES:
patent: 3991060 (1976-11-01), Curran
patent: 4160094 (1979-07-01), Curran et al.
Lettre et al., Chem. Ber., 85, 1952, pp. 397-407.

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