Quinoline carboxylic acid boric acid anhydrides and process...

C - Chemistry – Metallurgy – 07 – F

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C07F 5/02 (2006.01) C07F 5/04 (2006.01)

Patent

CA 1294968

A B S T R A C T The invention relates to new quinoline-3-carboxylic acid anhydrides of the general Formula I Image /I/ /wherein R stands for cyclopropyl, a group of the general Formula -CH2CR5R6R7 /wherein R5, R6 and R7 stand for hydrogen or halogen/7 or phenyl optionally substituted by 1 or 2 halogen, R1 and R2 stand for halogen, or an aliphatic acyloxy group containing 2 to 6 carbon atoms optionally substituted by halogen, or an aromatic acyloxy group containing 7 to 11 carbon atoms, R3 stands for chlorine or fluorine and R4 stands for hydrogen or fluorine/ and to the process for the preparation thereof which comprises reacting a compound of the general Formula II Image /II/ - 2 - 23305-1126 [wherein R, R3 and R4 are the same as stated above, R8 stands for hydrogen or alkyl containing 1 to 4 carbon atoms] with a compound of the Formula III HBF4 [III] or a borone derivative of the general Formula BX3 [IV] [wherein X stands for fluorine, chlorine or bromine] or an ether complex thereof, or a triacyloxy borate derivative of the general Formula V -B(OCOR9)3 [V] [wherein R9 stands for alkyl containing 1 to 5 carbon atoms optionally substituted by halogen, or aryl containing 6 to 10 carbon atoms]. The compounds of the general Formula I are new inter- mediates for the preparation of known quinoline-3-carboxylic acids showing antibacterial activity.

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