Method for the preparation of (-)piperazine benzoxazine derivati

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

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C07D49806

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055391109

ABSTRACT:
There is disclosed a method for the preparation of the antibacterial (-) piperazine benzoxazine derivative having formula I comprising the steps of reacting (+)2-aminomethylene-3-oxo-3-phenylpropionate derivative of formula II with a base in an organic polar solvent, to give a (-) benzoxazine derivative of formula III: and reacting the (-) benzoxazine derivative of formula III with a piperazine derivative of formula IV in an organic polar solvent. ##STR1##

REFERENCES:
patent: 5237060 (1993-08-01), Schriewer et al.
Hayakawa et al., "Synthesis an antibacterial Activities of Substituted 7-Oxo-2, 3-dihydro-7H-pyrido-[1,2,3,-de][1,4] benzoxazine-6-carboxylic Acids", Chem. Pharm. Bull., 32:4907-4913 (1984).
Schriewer et al., "Preparation of Chiral-bridged Quinolone Bactericides, including S-Ofloxacin", Chem. Abstr. 107:154342c (1987).
Mitscher et al., "Chiral DNA Gyrase Inhibitors. 2. Asymmetric Synthesis and Biological Activity of the Enantiomers of 9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[ 1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid (Ofloxacin)", J. Med. Chem., 30:2283 (1987).
"Levofloxacin", Drugs of the Future 17:559-563 (1992).
Masuzawa, Chemical Abstract 108: 112468p (1988).
Egawa, Chem. Abstract 108: 167489b (1988).

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