Preparation of pyridine dyes

Details Preparation of pyridine dyes Preparation of pyridine dyes

1996-07-30

1997-12-30

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546120, C07D47104, C09B 5500, C09B 2504

Patent

active

057032386

DESCRIPTION:

BRIEF SUMMARY
This application is the national phase of PCT/EP 95/00327 filed Jan. 31, 1995.
The present invention relates to a novel process for preparing methine or azamethine dyes on the basis of pyridine dyes by condensing an oxime- or formyl-pyridine or its tautomeric form with 5-membered aromatic heterocycles.
U.S. Pat. No. 5,079,365 discloses triazolopyridine dyes containing 5-membered aromatic heterocyclic radicals attached to the triazolopyridine via a nitrogen atom. Their preparation is effected by condensing the nitrosated heterocycle with the triazolopyridine.
GB-A-2 014 598 describes the condensation of a nitrosopyridone with a pyrazolone.
It is an object of the present invention to provide a novel process for preparing pyridine dyes in a simple manner and in good yield and purity.
We have found that this object is advantageously achieved by a process for preparing pyridine dyes of the formula I ##STR1## where X is nitrogen or CH, interrupted by one or more oxygen atoms in ether function, substituted or unsubstituted phenyl, or hydroxyl, -alkoxycarbonyl, or C(COOL.sup.1).sub.2, where L.sup.1 is in either case C.sub.1 -C.sub.8 -alkyl, which may be interrupted by 1 or 2 oxygen atoms in ether function, and a pyridine compound of the formula II ##STR2## where X, R.sup.1, R.sup.3, R.sup.4 and R.sup.5 are each as defined above, with a 5-membered aromatic heterocycle of the formula III -10.degree. to +100.degree. C.
The dyes of the formula I can exist in a plurality of tautomeric forms, which are all encompassed by the claims. For example, the compounds of the formula I where R.sup.4 =oxygen and R.sup.5 =methyl can exist inter alia in the following tautomeric forms: ##STR3## The same is true of the pyridine compounds of formula II. For example, the compounds of the formula II where R.sup.4 =oxygen can exist inter alia in the following tautomeric forms: ##STR4## Any substituted alkyl appearing in the abovementioned formulae may for example have as substituents, unless otherwise mentioned, phenyl, C.sub.1 -C.sub.4 -alkylphenyl, C.sub.1 -C.sub.4 -alkoxyphenyl, halophenyl, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.8 -alkylaminocarbonyloxy, C.sub.1 -C.sub.20 -alkoxycarbonyl, C.sub.1 -C.sub.20 -alkoxycarbonyloxy, and in the last two the alkyl chain may be interrupted by from 1 to 4 oxygen atoms in ether function and/or may be phenyl- or phenoxy-substituted, halogen, hydroxyl or cyano. The number of substituents in substituted alkyl is generally 1 or 2.
In any alkyl appearing in the abovementioned formulae with interruption by oxygen atoms in ether function, the number of oxygen atoms in ether function is preferably, unless otherwise stated, from 1 to 4 in particular 1 or 2.
Any substituted phenyl appearing in the abovementioned formulae may for example have as substituents, unless otherwise stated, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, in particular chlorine or bromine, or carboxyl. The number of substituents in substituted phenyl is generally from 1 to 3.
R.sup.2 can be derived for example from components of the pyrrole, thiazole, thiophene or indole series.
Important radicals R.sup.2 are for example those of the formulae IIIa to IIId ##STR5## where n is 0 or 1, the other hydrogen or else with the exception of hydroxyl the abovementioned radical R.sup.1 or together with the nitrogen atom bonding them together a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms, unsubstituted phenyl, substituted or unsubstituted benzyl, cyclohexyl, thienyl, hydroxyl or mono-C.sub.1 -C.sub.8 -alkylamino, unsubstituted or phenyl- or C.sub.1 -C.sub.4 -alkylphenyl-substituted C.sub.1 -C.sub.8 -alkyl, unsubstituted or phenyl- or C.sub.1 -C.sub.4 -alkylphenyl-substituted C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkanoylamino, C.sub.1 -C.sub.8 -alkylsulfonylamino or C.sub.1 -C.sub.8 mono- or dialkylaminosulfonylamino, C.sub.1 -C.sub.8 -alkoxycarbonyl or substituted or unsubstituted phenyl, and -alkoxy, C.sub.1 -C.sub.4 -alkylthio, substituted or unsubstituted phenyl or thienyl.
An

REFERENCES:
patent: 4908437 (1990-03-01), Hansen
patent: 5079365 (1992-01-01), Sens et al.
patent: 5101028 (1992-03-01), Schefczik
patent: 5105028 (1992-04-01), Dufour et al.

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