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US 2007/0191455 A1Published application
Substituted sym-triindole
AssigneeIhara Chemical Industry Co., Ltd.
InventorsHidetaka Hiyoshi, Hironobu Kumagai, Hideo Ooi
Life of this patent
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Abstract
A novel substituted Sym-triindole derivative that is applicable to a wide spectrum of uses, such as various electrification preventions, electrification controls, capacitors, batteries, chemical sensors, displays, organic EL materials, solar cells, photodiodes, phototransistors, nonlinear materials, photorefractive materials, rustproof agents, adhesives, fibers, antistatic paints, electrodeposition paints, plating primers, electric corrosion protections and the like. There is provided a substituted Sym-triindole derivative of the general formula (1) (wherein R1, R2, R3 and R4 are each independently hydrogen, a halogen, a C1-C6 alkyl or the like, provided that, in no event, all of R1, R2, R3 and R4 are hydrogen simultaneously).
Claims14
A substituted Sym-triindole derivative represented by the following general formula (1):
- wherein R1, R2, R3 and R4 are each independently hydrogen, halogen, C1-C6 alkyl group, C1-C6 haloalkyl group, substituted C1-C6 alkyl group, C2-C6 alkenyl group, substituted C2-C6 alkenyl group, C2-C6 alkynyl group, substituted C2-C6 alkynyl group, hydroxyl group, C1-C6 alkoxy group, aryloxy group, amino group, mono-substituted amino group, di-substituted amino group, acylamino group, mercapto group, C1-C6 alkylsulfenyl group, C1-C6 haloalkylsulfenyl group, arylsulfenyl group, substituted arylsulfenyl group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, aralkylsulfenyl group, arylsulfinyl group, substituted arylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, arylsulfonyl group, substituted arylsulfonyl group, sulfonic acid group (hydroxysulfonyl group), aryl group, substituted aryl group, cyano group, nitro group, formyl group, acyl group, carboxyl group, C1-C6 alkoxycarbonyl group, carbamoyl group, N-mono-substituted carbamoyl group, N,N-di-substituted carbamoyl group, hydrazonomethyl group (—CH═N—NH2 group), N-mono-substituted hydrazonomethyl group, N,N-di-substituted hydrazonomethyl group, oximemethyl group (hydroxyiminomethyl group), C1-C6 alkoxyiminomethyl group, or aryloxyiminomethyl group;
- R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group, or aryl C1-C6 alkyl group;
- wherein, in no event, all of R1, R2, R3 and R4 are hydrogen simultaneously.
A process for producing a substituted Sym-triindole derivative represented by the following general formula (1):
- wherein R1, R2, R3 and R4 are each independently hydrogen, halogen, C1-C6 alkyl group, C1-C6 haloalkyl group, substituted C1-C6 alkyl group, C2-C6 alkenyl group, substituted C2-C6 alkenyl group, C2-C6 alkynyl group, substituted C2-C6 alkynyl group, hydroxyl group, C1-C6 alkoxy group, aryloxy group, amino group, mono-substituted amino group, di-substituted amino group, acylamino group, mercapto group, C1-C6 alkylsulfenyl group, C1-C6 haloalkylsulfenyl group, aralkylsulfenyl group, arylsulfenyl group, substituted arylsulfenyl group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, arylsulfinyl group, substituted arylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, arylsulfonyl group, substituted arylsulfonyl group, sulfonic acid group (hydroxysulfonyl group), aryl group, substituted aryl group, cyano group, nitro group, formyl group, acyl group, carboxyl group, C1-C6 alkoxycarbonyl group, carbamoyl group, N-mono-substituted carbamoyl group, N,N-di-substituted carbamoyl group, hydrazonomethyl group (—CH═N—NH2 group), N-mono-substituted hydrazonomethyl group, N,N-di-substituted hydrazonomethyl group, oximemethyl group (hydroxyiminomethyl group), C1-C6 alkoxyiminomethyl group, or aryloxyiminomethyl group;
- R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group, or aryl C1-C6 alkyl group;
- wherein, in no event, all of R1, R2, R3 and R4 are hydrogen simultaneously), which process comprises reacting a substituted oxyindole represented by the following general formula (2):
- wherein R1, R2, R3, R4 and R5 have the same definitions as given above, with a phosphorus oxyhalide.
1 more element
A Sym-triindole derivative represented by the following general formula (3):
- wherein R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group, or aryl C1-C6 alkyl group;
- and R6 is hydrogen, formyl group, cyano group, C1-C6 alkoxycarbonyl group, dicyanovinyl group, aryl group or substituted aryl group.
A process for producing a Sym-triindole derivative represented by the following general formula (7):
- wherein R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- and R7 is hydrogen, formyl group, cyano group, C1-C6 alkoxycarbonyl group, aryl group or substituted aryl group, which process comprises reacting an N-substituted-5-halo-oxyindole represented by the following general formula (4):
- wherein R5 has the same definition as given above;
- and X is halogen, with a phosphorus oxyhalide to obtain an N-substituted-5-halo-triindole derivative represented by the following general formula (5):
- wherein R5 and X have the same definitions as given above, and further reacting the derivative of general formula (5) it with a boric acid compound represented by the following general formula (6):
- wherein R7 has the same definition as give above;
- and Ra and Rb are each independently hydrogen atom, C1-C6 alkyl group or optionally substituted phenyl group and may be combined to each other to form a ring.
4 more elements
A process for producing a Sym-triindole derivative represented by the following general formula (7):
- wherein R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- and R7 is hydrogen, formyl group, cyano group, C1-C6 alkoxycarbonyl group, aryl group or substituted aryl group, which process comprises reacting an N-substituted-5-halo-triindole derivative represented by the following general formula (5):
- wherein R5 has the same definition as given above;
- and X is halogen, with a boric acid compound represented by the following general formula (6):
- wherein R7 has the same definition as given above;
- and Ra and Rb are each independently hydrogen atom, C1-C6 alkyl group or optionally substituted phenyl group and may be combined to each other to form a ring.
3 more elements
A process for producing an N-substituted-5-halo-triindole derivative represented by the following general formula (5):
- wherein R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- and X is halogen, which process comprises reacting an N-substituted-5-halo-oxyindole represented by the following general formula (4):
- wherein R5 and X have the same definitions as given above, with a phosphorus oxyhalide.
A process for producing a Sym-triindole derivative represented by the following general formula (10):
- wherein R5 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- R8 is hydrogen or cyano group;
- and R9 is cyano group, carboxylic acid group, C1-C6 alkoxycarbonyl group, aryloxycarbonyl group, aryl group or substituted aryl group, which process comprises reacting a triindole derivative represented by the following general formula (8):
- wherein R5 has the same definition as given above, with a methylene compound represented by the general formula (9):
- wherein R8 and R9 have the same definitions as give above.
2 more elements
A Sym-triindole vinyl derivative represented by the following general formula (11):
- wherein R8 is hydrogen or cyano group;
- R9 is cyano group, carboxylic acid group, C1-C6 alkoxycarbonyl group, aryloxycarbonyl group, aryl group or substituted aryl group;
- and R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group.
A process for producing a Sym-triindole derivative represented by the following general formula (11):
- wherein R8 is hydrogen or cyano group;
- R9 is cyano group, carboxylic acid group, C1-C6 alkoxycarbonyl group, aryloxycarbonyl group, aryl group or substituted aryl group;
- and R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group, which process comprises reacting an oxyindole compound represented by the following general formula (12):
- wherein R10 has the same definition as given above and X is halogen, with a phosphorus oxyhalide to obtain a Sym-halo-triindole derivative represented by the following general formula (13):
- wherein R10 and X have the same definitions as given above, subjecting the derivative of general formula (13) to formylation with a formylating agent in the presence of butyllithium to obtain a Sym-formyltriindole derivative represented by the following general formula (14):
- wherein R10 has the same definition as given above, and reacting the derivative of general formula (14) with a methylene compound represented by the following general formula (9):
- (wherein R8 and R9 have the same definitions as given above).
4 more elements
A process for producing a Sym-triindole derivative represented by the following general formula (11):
- wherein R8 is hydrogen or cyano group;
- R9 is cyano group, carboxylic acid group, C1-C6 alkoxycarbonyl group, aryloxycarbonyl group, aryl group or substituted aryl group;
- and R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group, which process comprises reacting a Sym-formyltriindole derivative represented by the following general formula (14):
- wherein R10 has the same definition as given above, with a methylene compound represented by the following general formula (9):
- wherein R8 and R9 have the same definitions as given above.
2 more elements
A process for producing a Sym-formyltriindole derivative represented by the following general formula (14):
- wherein R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group), which process comprises subjecting a Sym-halo-triindole derivative represented by the following general formula (13):
- wherein R10 has the same definition as given above and X is halogen, to formylation with a formulating agent in the presence of butyllithium.
A Sym-triindole derivative represented by the following
- general formula (15):
- wherein R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- and R11 is aryl group or substituted aryl group.
A process for producing a Sym-triindole derivative represented by the following general formula (15):
- wherein R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- and R11 is aryl group or substituted aryl group, which process comprises reacting a Sym-halo-triindole derivative represented by the following general formula (13):
- wherein R10 has the same definition as given above and X is halogen with an acetylene derivative represented by the following general formula (16):
- R11R12 (16)
- wherein R11 has the same definition as given above and R12 is hydrogen or trimethylsilyl group.
2 more elements
A Sym-halo-triindole derivative represented by the following general formula (13):
- wherein R10 is C2-C12 alkyl group, substituted C2-C12 alkyl group, C2-C12 haloalkyl group or aryl C1-C6 alkyl group;
- and X is halogen.
Dependencies are inferred from the claim text.