Preparation of 1,8-bridged 4-quinoline-3-carboxylic acids

Details Preparation of 1,8-bridged 4-quinoline-3-carboxylic acids Preparation of 1,8-bridged 4-quinoline-3-carboxylic acids

1988-03-24

1989-08-22

Raymond, Richard L.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D26534

Patent

active

048597732

ABSTRACT:
A process for the preparation of a 1,8-bridged 4-quinolone-3-carboxylic acid of the formula ##STR1## comprising in a first reaction step reacting an enamine of the formula ##STR2## in an anhydrous, aprotic solvent with one equivalent of a base, at a temperature form 80.degree. C. to 180.degree. C., to give a 4-quinolone-3-carboxylic acid derivative of the formula ##STR3## and, in a second reaction step, reacting that with another equivalent of a base, to give the 1,8-bridged 4-quinolone-3-carboxylic acid derivative of the formula (I) and optionally converting the group Y into a carboxyl group or salt thereof. Both steps may be effected simultaneously in a one-pot process without intermediate isolation of the compound II. Some of the compounds are new. The old and new compounds are antibacterials and promote animal growth.

REFERENCES:
patent: 4571396 (1986-02-01), Hutt et al.
patent: 4777253 (1988-10-01), Mitscher et al.

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