Oxobenzofuranylide-dihydroindolone
First Claim
1. An oxobenzofuranylidene-dihydroindolone of formula trans-(Ia) or cis-(Ib) wherein A1 and A2 are each independently of the other unsubstituted or mono- to tetra-substituted 1,2-phenylene and R1 is hydrogen, C1-C25alkyl, C5-C12cycloalkyl, C6-C24aryl, a heteroaromatic radical, —
- (CH2)n—
COR2 or —
(CH2)m—
OR3, wherein R2 is hydroxy, —
OX, or, unsubstituted or mono- or poly-substituted by hydroxy, —
OX or by amino, C1-C25alkoxy, C1-C25alkylamino or C1-C25dialkylamino, di(C6-C24aryl)amino, C1-C12alkyl, C2-C24alkenyl, and X is a cation, and R3 is hydrogen or —
CO—
(C1-C25alkyl), 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C bond also may have been replaced by a corresponding ether unit, C—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 R1 is hydrogen and A2 is 1,2-phenylene, A1 is not 4-chloro-3,5-dimethyl-1,2-phenylene or 3,5-dimethyl-1,2-phenylene.
2 Assignments
0 Petitions
Accused Products
Abstract
Oxobenzofuranylidene-dihydroindolones of formulae trans-(Ia) and cis-(Ib)
and of formulae trans-(IIa) and cis-(IIb)
wherein
A1 and A2 are each independently of the other unsubstituted or mono- to tetra-substituted ortho-C6-C18arylene, and R1 is hydrogen or an organic radical, with the proviso that when R1 is hydrogen and A2 is 1,2-phenylene, A1 is not 9,10-anthraquinon-1,2-ylene, 4-chloro-3,5-dimethyl-1,2-phenylene or 3,5-dimethyl-1,2-phenylene, processes for their preparation and the use thereof.
-
Citations
5 Claims
-
1. An oxobenzofuranylidene-dihydroindolone of formula trans-(Ia) or cis-(Ib)
wherein A1 and A2 are each independently of the other unsubstituted or mono- to tetra-substituted 1,2-phenylene and R1 is hydrogen, C1-C25alkyl, C5-C12cycloalkyl, C6-C24aryl, a heteroaromatic radical, — - (CH2)n—
COR2 or —
(CH2)m—
OR3,wherein R2 is hydroxy, —
OX, or, unsubstituted or mono- or poly-substituted by hydroxy, —
OX or by amino, C1-C25alkoxy, C1-C25alkylamino or C1-C25dialkylamino, di(C6-C24aryl)amino, C1-C12alkyl, C2-C24alkenyl, andX is a cation, and R3 is hydrogen or —
CO—
(C1-C25alkyl), andn 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C bond also may have been replaced by a corresponding ether unit, C—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 R1 is hydrogen and A2 is 1,2-phenylene, A1 is not 4-chloro-3,5-dimethyl-1,2-phenylene or 3,5-dimethyl-1,2-phenylene.- View Dependent Claims (2, 3, 4, 5)
and A2 is - wherein
R8, R9, R11, R10, R12, R13, R14 and R15 are each independently of the others hydrogen, halogen, cyano, —
NO2, —
R16, —
NR17R18, —
NR19COR17, —
NR19COOR17, —
N═
CR17R18, —
CONR19R20, —
OR17, —
O—
(C1-C12alkylene)—
COOX, —
O—
(C1-C12alkylene)—
COOH,—
O—
(C1-C12alkylene)—
O—
CO—
R17, —
O—
(C1-C12alkylene)—
COOR17,—
O—
(C1-C12alkylene)—
CONR19R20, —
O—
(C1-C12alkylene)—
OR17,—
(C1-C12alkylene)—
O—
CO—
R17,—
(C1-C12alkylene)—
OR17, —
COOR17, —
(C1-C12alkylene)—
COOR17,—
(C1-C12alkylene)—
CONR19R20, —
(C1-C12alkylene)—
COOX, —
(C1-C12alkylene)—
COOH,—
COOX, —
COOH, —
SR17, —
SOR17, —
SO2R17, —
SO2NR19R20, —
SO3R17, SO3H or SO3X,
whereinR17, R18, R19 and R20 are each independently of the others hydrogen or R16, and R16 is, unsubstituted or mono- or poly-substituted by halogen, hydroxy, amino, oxo, carboxy, cyano, —
COOR18 or by —
COOX, C1-C25alkyl, C5-C12cycloalkyl or C2-C24alkenyl, which may be uninterrupted or interrupted one or more times by O, S or N—
(C1-C25alkyl), N—
(C2-C24alkenyl) 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, —
OR18, —
SR18, —
NR19R20, —
CONR19R20, —
COOR18, —
COOX, —
COOH, —
SO2R18, —
SO2NR19R20, —
SO3R18, —
SO3X, —
SO3H, —
NR19COR18 or by —
NR19COOR18, C6-C18aryl, C7-C18aralkyl or heteroaryl orR19 and R20, together with the nitrogen atom linking them, are unsubstituted or mono- to tetra-C1-C4alkyl-substituted pyrrolidinyl, piperidyl, piperazinyl or morpholinyl, or are carbazolyl, phenoxazinyl or phenothiazinyl.
- (CH2)n—
-
3. A composition comprising at least one oxobenzofuranylidene-dihydroindolone according to claim 1.
-
4. A process for the preparation of an oxobenzofuranylidene-dihydroindolone of formula trans-(Ia) or cis-(Ib) according to claim 1 by reaction of a benzofuranone compound with an isatin compound in the presence of an acidic or basic catalyst, which process comprises reacting a compound of formula (XXIX)
wherein A1 is unsubstituted or mono- to tetra-substituted 1,2-phenylene, with a compound of formula (XXX) or (XXXa) - wherein
Y is O, S, NH, N—
(C1-C24alkyl), N—
(C5-C18aryl) or N—
(C7-C28aralkyl) andHal is halogen, and A2 is unsubstituted or mono- to tetra-substituted 1,2-phenylene.
- wherein
-
5. An oxobenzofuranylidene-dihydroindolone according to claim 1, wherein A1 is
wherein R8, R9, R11, R10, R12, R13, R14 and R15 are each independently of the others hydrogen, halogen, cyano, — - NO2, —
R16, —
NR17R18, —
NR19COR17, —
NR19COOR17, —
N═
CR17R18, —
CONR19R20, —
OR17, —
O—
(C1-C12alkylene)—
COOX, —
O—
(C1-C12alkylene)—
COOH,—
O—
(C1-C12alkylene)—
O—
CO—
R17, —
O—
(C1-C12alkylene)—
COOR17,—
O—
(C1-C12alkylene)—
CONR19R20, —
O—
(C1-C12alkylene)—
OR17,—
(C1-C12alkylene)—
O—
CO—
R17,—
(C1-C12alkylene)—
OR17, —
COOR17, —
(C1-C12alkylene)—
COOR17,—
(C1-C12alkylene)—
CONR19R20, —
(C1-C12alkylene)—
COOX, —
(C1-C12alkylene)—
COOH,—
COOX, —
COOH, —
SR17, —
SOR17, —
SO2R17, —
SO2NR19R20, —
SO3R17, SO3H or SO3X,
whereinR17, R18, R19 and R20 are each independently of the others hydrogen or R16, and R16 is, unsubstituted or mono- or poly-substituted by halogen, hydroxy, amino, oxo, carboxy, cyano, —
COOR18 or by —
COOX, C1-C25alkyl, C5-C12cycloalkyl or C2-C24alkenyl, which may be uninterrupted or interrupted one or more times by O, S or N—
(C1-C25alkyl), N—
(C2-C24alkenyl) 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, —
OR18, —
SR18, —
NR19R20, —
CONR19R20, —
COOR18, —
COOX, —
COOH, —
SO2R18, —
SO2NR19R20, —
SO3R18, —
SO3X, —
SO3H, —
NR19COR18 or by —
NR19COOR18, C6-C18aryl, C7-C18aralkyl or heteroaryl, orR19 and R20, together with the nitrogen atom linking them, are unsubstituted or mono- to tetra-C1-C4alkyl-substituted pyrrolidinyl, piperidyl, piperazinyl or morpholinyl, or are carbazolyl, phenoxazinyl or phenothiazinyl.
- NO2, —
Specification