Production process of cyclic compound

Details Production process of cyclic compound Production process of cyclic compound

1997-11-26

1999-01-05

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

558389, 558390, 558430, 558432, 558433, 558434, C07D20712, C07C25503

Patent

active

058565183

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP96/01373 filed on May 23, 1996.


TECHNICAL FIELD

This invention relates to a novel process for the synthesis of material compounds to be used in the production of a quinolone derivative which is expected as an excellent antibacterial agent (JP-A-2-231475; the term "JP-A" as used herein means an "unexamined published Japanese patent application") and to an intermediate compound useful for the production.


BACKGROUND ART

The aforementioned compound represented by formula (VI): ##STR2## (wherein n is an integer of 2 to 5) has been produced via a multi-step production process using ethyl acetoacetate as the starting material (JP-A-2-231475). In addition, an optically active form of this compound is obtained by preparing a diastereomer compound having an optically active protecting group, isolating it using a preparative high performance liquid chromatography and then removing the protecting group (JP-A-3-95176). However, such a method requires complex handling, hence leaving room for the improvement as an industrial production process.
It is accordingly an object of the present invention to provide a process for the inexpensive, short-step and industrially advantageous production of nitrogen-containing heterocyclic compounds having a spiro-cyclic derivative.


DISCLOSURE OF INVENTION

Taking the aforementioned circumstances into consideration, the inventors of the present invention have conducted intensive studies and found that a compound of formula (I) ##STR3## can be obtained from a known compound of formula (IV) ##STR4## easily with a high yield, and that the compound of formula (I) obtained therefrom can be converted easily into a compound of the following formula (II). ##STR5##
The present invention has been accomplished on the basis of such findings.
The present inventors have also found a method by which the intended compound of formula (VI): ##STR6## can be obtained easily from a compound of formula (III-1): ##STR7## which is obtained by reducing the compound of formula (II).
Also, the present inventors have found that, when the compound (IV) is allowed to react with hydrogen cyanide in the presence of an optically single amine or a salt thereof, one of the thus formed two diastereomers is obtained on a preferential basis.
The present inventors have found also that one of the two diastereomers obtained above is easily epimerized when treated in a protic solvent, so that a mixture of two diastereomers can be obtained.
Accordingly, the present invention relates to a compound represented by formula (I): ##STR8## wherein n is an integer of 2 to 5; formula: ##STR9## wherein R.sup.a, R.sup.b and R.sup.c each represents a phenyl, phenylmethyl or naphthyl group (which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group), a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms; and atoms, with the proviso that a compound, in which n is 2, R.sup.1 is hydrogen atom and R.sup.2 is an ethyl group, is excluded, and a salt thereof.
The present invention also relates to a compound represented by formula (II): ##STR10## wherein n is an integer of 2 to 5; and formula: ##STR11## wherein R.sup.a, R.sup.b and R.sup.c each represents a phenyl, phenylmethyl or naphthyl group (which may be substituted with at least one substituent group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a halogen atom and a nitro group), a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, and a salt thereof.
The present invention also relates to a compound represented by formula (III): ##STR12## wherein n is an integer of 2 to 5; and ##STR13## wherein R.sup.a, R.sup.b and R.sup.c each represents a phenyl, phenylmethyl or naphthyl group (which may be substituted with at least one substituent group selected from the group consisting of an alkyl group havin

REFERENCES:
J. Chem. Soc., Chem. Commun., (3), (1985), pp. 119-120, Okano, Kohji et al International Search Report.

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