Oxobenzofuranylide-dihydroindolone

Details Oxobenzofuranylide-dihydroindolone Oxobenzofuranylide-dihydroindolone

2001-04-03

2003-01-07

Chang, Ceila (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S463000

Reexamination Certificate

active

06503937

ABSTRACT:

The present invention relates to oxobenzofuranylidene-dihydroindolones, to processes for their preparation and to the use thereof.
Bull. Soc. Chim. Fr., (1942), pages 801-804, describes a trans-3-(2-oxo-benzofuran-3-ylidene)-1,3-dihydro-indol-2-one (the reaction product of phthaloyl-6,7-coumarone-2 and isatin) and a trans-2-(2-oxo-benzofuran-3-ylidene)-1,2-dihydro-indol-3-one (the reaction product of phthaloyl-6,7-coumarone-2 and &agr;-isatinanilide).
Chem. Ber., Volume 54, (1921), pages 1213-1220, describes two 2-(2-oxo-benzofuran-3-ylidene)-1,2-dihydro-indol-3-ones: on the one hand, the condensation product of 4,6-dimethyl-coumarandione with indoxyl, and the condensation product of 5-chloro-4,6-dimethyl-coumarandione with indoxyl.
It is a disadvantage of the known processes that preparation is too complicated and too expensive for large-scale and commercial purposes.
The invention was therefore based on the problem of providing further oxobenzofuran-ylidene-dihydroindolones, which should preferably be suitable as colourants or fluorescent agents, especially for colouring or pigmenting organic or inorganic, high or low molecular weight material, especially high molecular weight organic material. The problem was also to find an economic process for the preparation of oxobenzofuranylidene-dihydroindolones. There have accordingly been found oxobenzofuranylidene-dihydroindolones of formulae trans-(Ia) and cis-(Ib)
and of formulae trans-(IIa) and cis-(IIb)
wherein
A
1
and A
2
are each independently of the other unsubstituted or mono- to tetra-substituted ortho-C
6
-C
8
arylene, and
R
1
is hydrogen, C
1
-C
25
alkyl, C
5
-C
12
cycloalkyl, C
6
-C
24
aryl, a heteroaromatic radical, —(CH
2
)
n
—COR
2
or —(CH
2
)
m
—OR
3
,
wherein R
2
is hydroxy, —OX, or, unsubstituted or mono- or poly-substituted by hydroxy, —OX or by amino, C
1
-C
25
alkoxy, C
1-C
25
alkylamino or C
1
-C
25
dialkyl-amino, di(C
6
-C
24
aryl)amino, C
1
-C
12
alkyl, C
2
-C
24
alkenyl, and
X is a cation, and
R
3
is hydrogen or —CO—(C
1
-C
25
alkyl), and
n and m denote each independently of the other a whole number in the range from 0 to 6, and
a single C—C bond also may have been replaced by a corresponding ether unit, C—O—C,
with the proviso that, when R
1
is hydrogen and A
2
is 1,2-phenylene, A
1
is not 9,10-anthraquinon-1,2-ylene, 4-chloro-3,5-dimethyl-1,2-phenylene or 3,5-dimethyl-1,2-phenylene.
Furthermore, improved processes for the preparation of oxobenzofuranylidene-dihydro-indolones and the use thereof have been found.
According to the invention X is a cation of an alkali metal such as lithium, sodium, potassium, an alkaline earth metal such as magnesium, calcium, strontium or is copper, zinc or aluminium or a quaternary amine such as [NR
4
R
5
R
6
R
7
]
+
, wherein
R
4
and R
5
are each independently of the other hydrogen, C
1
-C
25
alkyl, C
6
-C
18
aryl or C
7
-C
28
aralkyl, and
R
6
and R7 are each independently of the other hydrogen, C
6
-C
18
aryl, C
7
-C
18
aralkyl or, unsubstituted or mono- or poly-substituted by halogen, hydroxy or by C
1
-C
12
alkoxy,
C
1
-C
25
alkyl or C
2
-C
24
alkenyl, or R
6
and R
7
together with the common nitrogen atom denote an unsubstituted or mono- to tetra-C
1
-C
4
alkyl-substituted pyrrolidine, piperidine, piperazine or morpholine, carbazole, phenoxazine or phenothiazine radical.
In a preferred embodiment, A
1
and A
2
are each independently of the other ortho-C
6
-C
18
-arylene, which may be, for example, substituted or unsubstituted 1,2-phenylene, 1,2-naphthylene, 2,3-naphthylene, 1,2-phenanthrylene, 2,3-phenanthrylene, 3,4-phenanthrylene, 9,10-phenanthrylene, 1,2-anthracenyl, 2,3-anthracenyl or 1,2-anthraquinonylene, 2,3-anthraquinonylene.
Substituents that come into consideration for ortho-C
6
-C
18
arylene are, for example, bivalent radicals such as 1,3-butadien-1,4-ylene or —CH═CH—NH—, or fused-on substituted or unsubstituted 5- or 6-membered rings, and also, if desired, other substituents (see below).
In an especially preferred embodiment, A
1
is
and A
2
is
R
8
, R
9
, R
11
, R
10
, R
12
, R
13
, R
14
and R
15
being each independently of the others hydrogen, halogen, cyano, —NO
2
, —R
16
, —NR
17
R
18
, —NR
19
COR
17
, —NR
19
COOR
17
, —N═CR
17
R
18
,
—CONR
19
R
20
, —OR
17
, —O—(C
1
-C
12
alkylene)-COOX, —O—(C
1
-C
12
alkylene) -COOH,
—O—(C
1
-C
12
alkylene)—O—CO—R
17
, —O—(C
1
-C
12
alkylene)-COOR
17
, —O—(C
1
-C
12
alkylene)-CONR
19
R
20
, —O—(C
1
-C
12
alkylene)-OR
17
, —(C
1
-C
12
alkylene)-O—CO—R
17
,
—(C
1
-C
12
alkylene)-OR
17
, —COOR
17
, —(C
1
-C
12
alkylene)-COOR
17
, —(C
1
-C
12
alkylene)-CONR
19
R
20
,
—(C
1
-C
12
alkylene)-COOX, —(C
1
-C
12
alkylene)-COOH, —COOX, —COOH, —SR
17
,
—SOR
17
, —SO
2
R
17
, —SO
2
NR
19
R
20
, —SO
3
R
17
, SO
3
H or SO
3
X,
wherein
R
17
, R
18
, R
19
and R
20
are each independently of the others hydrogen or R
16
, and
R
16
is, unsubstituted or mono- or poly-substituted by halogen, hydroxy, amino, oxo, carboxy, cyano, —COOR
18
- or by —COOX, C
1
-C
25
alkyl, C
5
-C
12
cycloalkyl or C
2
-C
24
alkenyl, which may be uninterrupted or interrupted one or more times by O, S or N—(C
1
-C
25
alkyl), N—(C
2
-C
24
alkenyl) when the alkyl has more than two and the alkenyl more than three carbon atoms, or is, unsubstituted or mono- or poly-substituted by halogen, nitro, cyano, —OR
18
, —S
18
, —NR
19
R
20
, —CONR
19
R
20
, —COOR
18
, —COOX, —COOH, —SO
2
R
18
, —SO
2
NR
19
R
20
, —SO
3
R
18
, —SO
3
X, —SO
3
H, —NR
19
COR
18
or by —NR
19
COOR
18
, C
6
-C
18
aryl, C
7
-C
18
aralkyl or heteroaryl,
or
R
19
and R
20
, together with the nitrogen atom linking them, are unsubstituted or mono- to tetra-C
1
-C
4
alkyl-substituted pyrrolidinyl, piperidyl, piperazinyl or morpholinyl, or are carbazolyl, phenoxazinyl or phenothiazinyl,
 it being possible, optionally, for R
8
and R
9
, R
9
and R
11
, R
11
and R
10
and for R
12
and R
13
, R
13
and R
14
or R
14
and R
15
additionally to form, in each case, a substituted or unsubstituted 5- or 6-membered ring.
In a further especially preferred embodiment, at least one of the substituents R
8
, R
9
, R
11
, R
10
, R
12
, R
13
, R
14
and R
15
is a radical selected from the group consisting of the radicals Z
1
, Z
2
, Z
3
and Z4
wherein
R
22
, R
23
, R
24
, R
25
, R
26
, R
27
and R
28
are each independently of the others hydrogen, halogen, cyano, —NO
2
, —R
16
, —NR
17
R
18
, —NR
19
COR
17
, —NR
19
COOR
17
, —N═CR
17
R
18
, —CONR
19
R
20
, —OR
17
,
—O—(C
1
-C
12
alkylene)-COOX, —O—(C
1
-C
12
alkylene)-COOH, —O—(C
1
-C
12
alkylene)-O—CO—R
17
,
—O—(C
1
-C
12
alkylene)-COOR
17
, —O—(C
1
-C
12
alkylene)-CONR
19
R
20
, —O—(C
1
-C
12
alkylene)-OR
17
,
—(C
1
-C
12
alkylene)-O—CO—R
17
, —(C
1
-C
12
alkylene)-OR
17
, —COOR
17
, —(C
1
-C
12
alkylene)-COOR
17
,
—(C
1
-C
12
alkylene)-CONR
19
R
20
, —(C
1
-C
12
alkylene)-COOX, —COOX, —COOH, —SR
17
, —SOR
17
,
—SO
2
R
17
, —SO
2
NR
19
R
20
, —SO
3
R
17
or SO
3
X, SO
3
H, the radicals R
17
, R
18
, R
19
, R
20
being as defined above, and
R
21
, independently of R
1
, has the same definition as R
1
, and
A
3
is a single bond or is, unsubstituted or mono- or poly-substituted by C
1
-C
25
alkyl,
C
6
-C
24
aryl, halogen, hydroxy, —OX, oxo, cyano, —COOR
6
, —COOX, —COOH, —SO
3
R
6
, —SO
3
X or by —SO
3
H, C
1
-C
24
alkylene or C
5
-C
12
cycloalkylene or —OOC—(C
1
-C
24
alkylene)-COO—,
—COO—(C
1
-C
24
alkylene)-OOC—, —NR
19
CO—(C
1
-C
24
alkylene)-CONR
19
—,
—CONR
19
—(C
1
-C
24
alkylene)—NR
19
CO—; C
6
-C
24
arylene or heteroarylene.
A further especially preferred embodiment relates to oxobenzofuranylidene-dihydroindolones wherein A
1
is
wherein R
8
, R
9
, R
11
and R
10
are as defined above,
and A
2
is a bivalent radical Z
5
or Z
6
wherein R
13
, R
14
, R
21
, R
22
, R
23
, R
24
and R
27
are as defined above.
A further preferred embodiment relates to oxobenzofuranylidene-dihydroindolone of formula (Ll)
wherein
P
1
, P
2
, P
3
are each independently of the others a radical selected from the group consisting of the radicals Z
1
, Z
2
, Z
3
and Z
4
, and A
4
is a trivalent radical, preferably
The c

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