Indolenine derivative

Details Indolenine derivative Indolenine derivative

1990-05-14

1991-10-08

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548490, 548430, A61K 3140, C07D20956, C07D20904, C07D49100

Patent

active

050555898

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to novel indolenine derivatives.


DISCLOSURE OF THE INVENTION

The indolenine derivative of the present invention is a compound undisclosed in literature and is represented by the formula (1) ##STR2## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, X and Y are the same or different and each represent a methylene group or an oxygen atom.
The compounds of the present invention represented by the formula (1) are useful as an intermediate for synthesizing the cyanine compounds represented by the formula (8) which appear hereinafter.
The compounds of the present invention can be prepared by various processes, and can be easily prepared, for example, by the following preferable process. ##STR3##
The conventional aniline derivative of the formula (2) is reacted with the conventional 3-bromo-3-methyl-2-butanone of the formula (3) in the presence of an acid scavenger. Useful acid scavengers are, for example, pyridine, triethylamine, tri-n-propylamine, tri-n-butylamine and like tertiary amines; sodium carbonate, potassium carbonate, calcium carbonate and like alkali metal salts of carbonic acids; sodium acetate, potassium acetate, calcium acetate and like alkali metal salts of acetic acids; etc. The acid scavenger is used in an amount of usually about 0.3 to about 5 moles, preferably about 0.5 to about 1.5 moles, per mole of the compound of the formula (2). The proportions of the compounds of the formulas (2) and (3) are usually about 0.3 to about 5 moles, preferably about 0.5 to about 1.5 moles, of the latter per mole of the former. The reaction is conducted usually at a temperature in the range of from ambient temperature to about 200.degree. C., preferably about 50 to about 150.degree. C. and is completed usually in several hours to about 25 hours, preferably about 5 to about 15 hours.
The compound of the present invention thus obtained can be readily isolated from the reaction mixture and purified by commonly employed separation and purification means such as recrystallization, column chromatography or the like.
The compound of the present invention can be made into the cyanine compound of the formula (8) by the following process: ##STR4##
In the above formulas, R.sup.1, X and Y are as defined above, Z.sub.1 is an acidic residue other than perchlorate residue and tetrafluoroborate residue, Z.sub.2 is a perchlorate residue or a tetrafluoroborate residue, and R.sup.2 is an optionally substituted lower alkyl group.
The compound represented by the formula (4a) can be prepared by causing an alkylating agent to act on the indolenine derivative of the formula (1). Examples of the alkylating agent are methyl toluenesulfonate, ethyl toluenesulfonate, n-propyl toluenesulfonate, isopropyl toluenesulfonate, n-butyl toluenesulfonate and like alkyl toluenesulfonates, ethyl bromide, n-propyl bromide, n-butyl bromide, ethyl iodide, n-propyl iodide, n-propyl chloride, n-butyl chloride and like halogenated alkyls, dimethyl sulfate, diethyl sulfate and like dialkyl sulfates, a mixture of acids and epoxy compounds (for example, a mixture of hydrochloric acid, sulfuric acid or like inorganic acid, acetic acid, propionic acid or like organic acid and ethylene oxide, propylene oxide or the like), methyl sultone, ethyl sultone, propyl sultone, butyl sultone and like alkyl sultones, etc. The amount of the alkylating agent to be used is usually about 0.3 to about 5 moles, preferably about 0.5 to about 2 moles, per mole of the compound of the formula (1). The reaction is carried out in the presence or the absence of a solvent. Illustrative of useful solvents are toluene, xylene and like alkylbenzenes; n-octane, n-decane, cyclohexane, decalin and like aliphatic hydrocarbons; benzene, napthalin, tetralin and like aromatic hydrocarbons; trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene and like halogenated hydrocarbons, etc. The reaction is effected usually at a temperature in the range of from room temperature to about 200.degree. C., preferably about 50.degr

REFERENCES:
patent: 4062870 (1977-12-01), Watts

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