Benzene derivatives having a heterocyclic radical

Details Benzene derivatives having a heterocyclic radical Benzene derivatives having a heterocyclic radical

1998-01-26

1999-03-23

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548131, 548136, 548143, C07D27106, C07D271107, C07D28508, C07D28512

Patent

active

058861874

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP96/03224 filed Jul. 22, 1996.
The present invention relates to novel benzene derivatives of the formula I ##STR2## where by 1 or 2 oxygen or sulfur atoms in ether form or 1 or 2 nonadjacent amino, C.sub.1 -C.sub.4 -alkylamino or C.sub.1 -C.sub.4 -alkanoylimino groups, hydroxyl or a group which can be removed under alkaline reaction conditions, -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, amino, hydroxysulfonyl or a radical of the formula Z--S(O).sub.n --Y, where n, Z and Y each have the abovementioned meanings, and has 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen.
It is an object of the present invention to provide novel benzene derivatives having a heterocyclic radical, and which furthermore have a thioether, sulfoxide or sulfonyl group. The novel benzene derivatives should advantageously be suitable for the production of dyes.
We have found that this object is achieved by the benzene derivatives of the formula I described in greater detail at the outset.
All alkyl and alkylene groups occurring in the abovementioned formula can be either straight-chain or branched.
Radicals R.sup.1 and R.sup.2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, fluorine, chlorine or bromine.
Radicals Z are, for example, CH.sub.2, (CH.sub.2).sub.2, (CH.sub.2).sub.3, (CH.sub.2).sub.4, (CH.sub.2).sub.5, (CH.sub.2).sub.6, CH(CH.sub.3)CH.sub.2, CH(CH.sub.3)CH(CH.sub.3), (CH.sub.2).sub.2 0(CH.sub.2).sub.2, (CH.sub.2).sub.2, (CH.sub.2).sub.2 O(CH.sub.2).sub.2 O(CH.sub.2).sub.2, (CH.sub.2).sub.2 S(CH.sub.2).sub.2, (CH.sub.2).sub.3 S(CH.sub.2).sub.2, (CH.sub.2).sub.2 S(CH.sub.2).sub.2 S(CH.sub.2), (CH.sub.2).sub.2 NH(CH.sub.2).sub.2, (CH.sub.2).sub.3 NH(CH.sub.2).sub.2, (CH.sub.2).sub.2 NH(CH.sub.2).sub.2 NH (CH.sub.2).sub.2, ##STR3##
The radical Q is hydroxyl or a group which can be removed under alkaline reaction conditions. Such groups are, for example, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, OSO.sub.3 H, SSO.sub.3 H, OP(O) (OH).sub.2, C.sub.1 -C.sub.4 -alkylsulfonyloxy, phenylsulfonyloxy, C.sub.1 -C.sub.4 -alkanoyloxy, C.sub.1 -C.sub.4 -dialkylamino or a radical of the formula ##STR4## where L.sup.1, L.sup.2 and L.sup.3 independently of one another in each case have the meaning of C.sub.1 -C.sub.4 -alkyl or benzyl and An.crclbar. in each case has the meaning of one equivalent of an anion. Suitable anions here are, for example, fluoride, chloride, bromide, iodide, mono-, di- or trichloroacetate, methanesulfonate, benzenesulfonate or 2- or 4-methylbenzenesulfonate.
Het is the radical of a 5- or 6-membered aromatic heterocyclic ring which has 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen.
Suitable heterocyclic parent structures, which can carry substituents, from which the radicals Het are derived are, for example, pyrrole, furan, thiophene, pyrazole, imidazole, oxazole, thiazole, isothiazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine or pyrazine.
Suitable substituents for the heterocyclic parent structures are, for example, C.sub.1 -C.sub.4 -alkyl, phenyl, halogen, cyano, carboxyl or C.sub.1 -C.sub.4 -alkoxycarbonyl.
To be emphasized here are 5-membered heterocycles, in particular those which have 3 heteroatoms. Particularly to be mentioned are 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole or 1,3,4-thiadiazole.
Preferred benzene derivatives of the formula I are those in which is 0 or 2.
Furthermore preferred benzene derivatives of the formula I are those in which Z is C.sub.1 -C.sub.4 -alkylene which can be interrupted by an oxygen atom in ether form.
Furthermore preferred benzene derivatives of the formula I are those in which Y is 2-hydroxyethyl.
Furthermore preferred benzene derivatives of the formula I are those in which R.sup.1 has the abovementioned meaning and R

REFERENCES:
I. A. Mazur et al; Synthesis of 2,3-Dihydro and 2,3,5,6,-Tetrahydro No.3, 19 Jan. 1970, p. 334.

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