CN102167701B - Fluorine-containing diphenyl-pyrrolo-pyrrolidinedione (DPP) pigments and preparation method thereof - Google Patents
Fluorine-containing diphenyl-pyrrolo-pyrrolidinedione (DPP) pigments and preparation method thereof Download PDFInfo
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Abstract
The invention relates to fluorine-containing 1,4-dione pyrrolo[3,4,C]pyrrole derivatives with a structure shown as a formula I. The fluorine-containing 1,4-dione pyrrolo[3,4,C]pyrrole derivatives can be used as pigments, and enrich the color spectrum of the conventional DPP pigments. In the formula I, A and B are respectively selected from aromatic radical, heterocyclic radical, fluorine-containing aromatic radical and fluorine-containing heterocyclic group, and at least one of A and B is the fluorine-containing aromatic radical or the fluorine-containing heterocyclic group, wherein the heteroatoms of the heterocyclic group or the fluorine-containing heterocyclic group are selected from one or more of N, O and S, and the number of the heteroatoms is an integer from 1 to 3.
Description
Technical field
The present invention relates to a kind of fluorine-containing Pyrrolopyrrole derivatives, specifically, relate to a kind of fluorine-containing Isosorbide-5-Nitrae-diketone pyrroles [3,4-C] and pyrrole derivative.
Background technology
Isosorbide-5-Nitrae-diketone pyrroles [3,4-C] and azoles are a kind of high performance pigments (being called for short DPP class pigment).DPP class pigment has high tinctorial strength, good flowability, dispersiveness and acidproof/alkalescence and solvent resistance, is highly suitable for automobile finish, plastics and high-grade industrial coating.
Yet the chromatogram of existing DPP class pigment is essentially ruddiness, and chromatogram is narrower, and is still unsatisfactory.
Summary of the invention
The present inventor introduces fluorine atom in existing Isosorbide-5-Nitrae-diketone pyrroles [3,4-C] and azoles, obtain a kind of fluorine-containing Isosorbide-5-Nitrae of novelty-diketone pyrroles [3,4-C] and pyrrole derivative, find that its coloured light is that gold-tinted is red, has enriched the chromatogram of existing DPP class pigment.
Fluorine-containing Isosorbide-5-Nitrae of the present invention-diketone pyrroles [3,4-C] and pyrrole derivative, its structure is suc as formula shown in the I:
Among the formula I, A and B independently are selected from respectively: a kind of in aromatic ring yl, heterocyclic radical, fluorine-containing aromatic ring yl or the fluorine-containing heterocyclic radical heterocyclic radical, and have at least one to be fluorine-containing aromatic ring yl or fluorine-containing heterocyclic radical heterocyclic radical among A and the B;
Wherein, the heteroatoms of said heterocyclic radical or fluorine-containing aromatic ring yl is selected from: among N, O or the S one or two or more kinds (containing two kinds), heteroatomic number is 1～3 integer.
The present invention also provides the method for compound shown in a kind of preparation formula I, and its key step is: by lactam analog compound (its structure is suc as formula shown in the II) and corresponding nitrile (BCN) reaction, make target compound (compound shown in the formula I).
Among the formula II, R is that (preferred R is C to alkyl or virtue (perfume (or spice)) base
1～C
6The straight or branched alkyl, preferred R is C
1～C
3The straight or branched alkyl); The definition of A is described identical with preamble.
Embodiment
In preferred technical scheme of the present invention, A and B independently are selected from respectively: C
6～C
20Aromatic ring yl or fluorine-containing C
6～C
20Aromatic ring yl is a kind of, and has at least one to be fluorine-containing C among A and the B
6～C
20Aromatic ring yl;
Preferred technical scheme is that A and B independently are selected from respectively: C
6～C
12Aromatic ring yl or fluorine-containing C
6～C
12Aromatic ring yl is a kind of, and has at least one to be fluorine-containing C among A and the B
6～C
12Aromatic ring yl;
Best technical scheme is, A and B independently are selected from respectively: a kind of in the group shown in group shown in group, the formula V shown in group, the formula IV or the formula VI shown in phenyl, xenyl, naphthyl, the formula III, and have at least one to be group shown in formula III, IV, V or the VI among A and the B:
Wherein: m is 1～7 integer; N is 1～5 integer; P is that 0～5 integer, q are 0～4 integer, and p and q are not zero simultaneously; Curves mark place is the position of substitution.
The method of compound shown in the preparation formula I provided by the present invention (target compound), its synthetic route is as follows:
Specifically comprise the steps:
(1) under 0 ℃, (mass concentration is 10%～20% in the NaOH solution of compound shown in the formula VIII (specifically as methyl aceto acetate etc.),) drip compound shown in the formula VII, dropwise, kept at least 1 hour at room temperature (20 ℃～30 ℃) state, add again ammonium chloride, stir after at least 0.5 hour, obtain compound shown in the formula IX through extraction, drying and underpressure distillation successively;
(2) under alkaline condition, in the ethanolic soln of compound shown in the formula IX, drip ethyl bromoacetate, reflux after at least 24 hours, filter out solid inorganic alkali or salt, and with washing with alcohol inorganic salt salt, filtrate steaming removal solvent, underpressure distillation obtains compound shown in the formula X;
(3) compound shown in the formula X and ammonium acetate were refluxed 20 hours in acetic acid at least, reaction solution is poured in the frozen water, filters, and washing leaching cake, filter cake obtain compound shown in the formula II after with the methylene dichloride recrystallization;
(4) having under rare gas element (such as nitrogen etc.) existence condition, with compound shown in the formula II and nitrile compounds (BCN, wherein the definition of B is described identical with preamble) in the tertiary amyl alcohol solution of sodium tert-amyl alcohol, refluxed at least 6 hours, then the gained reaction solution is joined (protonated) in the mixing solutions that is formed by methyl alcohol, water and acetic acid, filter and washing leaching cake, obtain target compound (compound shown in the formula I) after the drying.
Disclosed fluorine-containing Isosorbide-5-Nitrae-diketone pyrroles [3,4-C] and pyrrole derivative can be used as pigment, and it has enriched the chromatogram of existing DPP class pigment.
The present invention is further elaborated below by embodiment, and listed embodiment does not limit protection scope of the present invention.
In the following example.Said room temperature is 20 ℃～30 ℃
Embodiment 1
(1) mass concentration is 15% aqueous sodium hydroxide solution 150ml at ice bath borehole cooling to 0 ℃, then add methyl aceto acetate (13.00g, 0.1mol), under the mechanical stirring, slowly drip Benzoyl chloride (15.47g, 0.11mol) in above mixed solution, drip off finish after, be warming up to room temperature, TLC follows the tracks of reaction, and (reaction times is about 1 hour, silica-gel plate, developping agent ethyl acetate: sherwood oil=1: 1 (v/v)) to terminal, add ammonium chloride (5.30g, 0.1mol), behind the stirring 0.5h, petroleum ether extraction (30ml * 3) water, merge organic phase, behind the anhydrous magnesium sulfate drying, underpressure distillation obtains colorless oil 15.99g, structure is suc as formula shown in the IX-1, productive rate 83.2%;
1H-NMR(400Hz，CDCl
3)：δ＝1.23-1.27(t，3H)，3.99(s，2H)，4.19-4.28(m，2H)，7.46-7.50(t，2H，)，7.56-7.61(t，1H)，7.93-7.97(t，2H，)；
13C-NMR：δ＝14.1，48.2，61.5，128.4，128.7，133.5，133.9，170.1，190.5；MS：M
+＝192.1。
(2) compound (10.19g, 0.053mol), K shown in the formula IX-1
2CO
3(7.62g, 0.055mol) is suspended in the 100ml ethanolic soln reflux 24h with ethyl bromoacetate (9.02g, 0.054mol).Then cool to room temperature filters out solid matter, and uses the washing with alcohol solid, merges ethanolic soln, and underpressure distillation obtains colorless oil 11.73g, and structure is suc as formula shown in the X-1, productive rate 79.5%.
1H-NMR(400Hz，CDCl
3)：δ＝1.15-1.19(t，3H)，1.22-1.26(t，3H)，3.00-3.14(m，2H)，4.12-4.18(m4H)，4.86-4.90(t，1H)，7.49-7.53(t，2H)，7.60-7.63(t，1H)，8.04-8.06(t，2H)；
13C-NMR：14.1，35.2，49.1，61.3，128.6，128.8，133.5，135.5，169.9，173.3，195.1；MS：M
+＝278.3。
(3) compound (11.13g, 0.04mol) shown in the formula X-1 and ammonium acetate (12.31g, the 0.16mol) 20h that refluxes in 50ml acetic acid, TLC controls reaction end.Then reactant is poured in the 200ml frozen water, has at once a large amount of light yellow solids to separate out, and filters, and uses the frozen water washing leaching cake, after the drying, uses the methylene dichloride recrystallization, obtains 7.56 white solids, and structure is suc as formula shown in the II-1, productive rate 81.7%;
1H-NMR(400Hz，CDCl
3)：δ＝1.03-1.07(t，3H)，3.33-3.35(d，2H)，3.92-3.98(m，2H)，7.40-7.47(m，3H)，7.54-7.58(m，2H)，10.64(br?s，1H)；
13C-NMR：δ＝14.4，48.2，61.1，127.8，128.5，132.3，133.9，168.8，192.7；MS：M
+＝231.1；mp：180-182℃。
(4) under nitrogen protection, sodium Metal 99.5 (0.92g, 0.04mol) is joined in the 30ml tertiary amyl alcohol, then add the FeCl of catalytic amount
3, reflux, sodium reacts complete behind the 2h, adds cyanophenyl (2.06g, 0.02mol), and compound shown in the formula II-1 (4.62g, 0.02mol) is dissolved in the 20ml tertiary amyl alcohol, slowly is added drop-wise in the mentioned solution, and 2h dropwises.Then under reflux state, keep 5h.Reaction solution is cooled to 60 ℃, adds the mixing solutions 50ml that is comprised of methyl alcohol, water and acetic acid, and behind the stirring at room 2h, backflow 2h filters, and methyl alcohol and water washing filter cake with hot obtain gold-tinted red solid 4.58g, and structure is suc as formula shown in the I-1, productive rate 79.9%.
Embodiment 2
Under nitrogen protection, sodium Metal 99.5 (0.92g, 0.04mol) is joined in the 30ml tertiary amyl alcohol, then add the FeCl of catalytic amount
3, reflux, sodium reacts complete behind the 2h, adds phenyl cyanophenyl (3.58g, 0.02mol), and compound shown in the formula II-1 (4.62g, 0.02mol) is dissolved in the 20ml tertiary amyl alcohol, slowly is added drop-wise in the mentioned solution, and 2h dropwises.Then under reflux state, continue reaction 5h.Reaction solution is cooled to 60 ℃, adds the mixing solutions 50ml of methyl alcohol, water and acetic acid, and behind the stirring at room 2h, backflow 2h filters, and methyl alcohol and water washing filter cake with heat obtain purple light red solid 5.88g, and structure is suc as formula shown in the I-2, productive rate 80.7%;
Embodiment 3
Under nitrogen protection, sodium Metal 99.5 (0.92g, 0.04mol) is joined in the 30ml tertiary amyl alcohol, then add the FeCl of catalytic amount
3, reflux, sodium reacts complete behind the 2h, adds nitrilthiophene (2.18g, 0.02mol), and compound shown in the formula II-1 (4.62g, 0.02mol) is dissolved in the 20ml tertiary amyl alcohol, slowly is added drop-wise in the mentioned solution, and 2h dropwises.Then under reflux state, continue reaction 5h.Reaction solution is cooled to 60 ℃, adds the mixing solutions 50ml of methyl alcohol, water and acetic acid, and behind the stirring at room 2h, backflow 2h filters, and methyl alcohol and water washing filter cake with heat obtain red solid 4.54g, and structure is suc as formula shown in the I-3, productive rate 77.2%.
Embodiment 4
(1) the aqueous sodium hydroxide solution 150ml of mass concentration 15% is at ice bath borehole cooling to 0 ℃, then add methyl aceto acetate (13.00g, 0.1mol), under the mechanical stirring, slowly drip fluorobenzoyl chloride (15.90g, 0.11mol) in above mixed solution, after dropwising, be warming up to room temperature, TLC follows the tracks of reaction, and (reaction times is about 1 hour, silica-gel plate, ethyl acetate: sherwood oil=1: 1 (v/v)) to terminal, add ammonium chloride (5.30g, 0.1mol), behind the stirring 0.5h, petroleum ether extraction (30ml * 3) water, merge organic phase, behind the anhydrous magnesium sulfate drying, underpressure distillation obtains light yellow oil 17.02g, shown in the structural formula IX-2, productive rate 81.0%;
1H-NMR(400Hz，CDCl
3)：δ＝1.21-1.25(t，3H)，3.97(s，2H)，4.15-4.21(m，2H)，7.10-7.14(t，2H，)，7.96-7.98(d，2H)；
13C-NMR：δ＝14.09，45.96，61.55，115.86.131.39，167.39，164.44，167.38，191.03，191.07；MS：M
+＝210.1。
(2) compound (11.11g, 0.053mol), K shown in the formula IX-2
2CO
3(7.62g, 0.055mol) is suspended in the 100ml ethanolic soln with ethyl bromoacetate (9.02g, 0.054mol), reflux 24h, and TLC controls reaction end.Then cool to room temperature filters out solid matter, and uses the washing with alcohol solid, merges ethanolic soln, and underpressure distillation obtains colorless oil 12.02g, and structure is suc as formula shown in the X-2, productive rate 76.4%;
1H-NMR(400Hz，CDCl
3)：δ＝1.19-1.25(m，6H)，3.10-3.15(m，2H)，4.11-4.17(m，4H)，4.83-4.87(t，1H)，7.56-7.62(m，2H)，8.59-8.65(m，2H)；
13C-NMR：δ＝13.7，13.9，33.1，49.4，60.8，61.6，128.5，128.7，133.5，135.8，168.5，171.0；MS：M
+＝296.1。
(3) compound (11.92g shown in the formula X-2,0.04mol) and ammonium acetate (12.31g, the 0.16mol) 20h that in 50ml acetic acid, refluxes, then reactant is poured in the 200ml frozen water, there are at once a large amount of light yellow solids to separate out, filter, use the frozen water washing leaching cake, after the drying, use the methylene dichloride recrystallization, obtain the 7.92g white solid, structure is suc as formula shown in the II-2, productive rate 80.2%.
1H-NMR(400Hz，CDCl
3)：δ＝1.17-1.21(t，3H)，3.49(s，2H)，4.10-4.14(m，2H)，7.41-7.49(m，2H)，7.58-7.62(m，2H)，9.12(br?s，1H)；
13C-NMR：δ＝14.5，39.1，60.4，105.0，128.6，129.1，130.0，130.9，151.6，163.6，177.5；MS：M
+＝249.1；mp：190-192℃；
(4) under nitrogen protection, sodium Metal 99.5 (0.92g, 0.04mol) is joined in the 30ml tertiary amyl alcohol, then add the FeCl of catalytic amount
3, reflux, sodium reacts complete behind the 2h, adds 3,5-difluorobenzonilyile (2.78g, 0.02mol), and compound shown in the formula II-2 (5.00g, 0.02mol) is dissolved in the 20ml tertiary amyl alcohol, slowly is added drop-wise in the mentioned solution, and 2h dropwises.Then under reflux state, keep 5h.Reaction solution is cooled to 60 ℃, adds the mixing solutions 50ml that is comprised of methyl alcohol, water and acetic acid, and behind the stirring at room 2h, backflow 2h filters, and methyl alcohol and water washing filter cake with hot obtain gold-tinted red solid 5.11g, and structure is suc as formula shown in the I-4, productive rate 75.0%.
Embodiment 5
(1) mass concentration be in 15% the aqueous sodium hydroxide solution 150ml at ice bath borehole cooling to 0 ℃, then add methyl aceto acetate (13.00g, 0.1mol), under the mechanical stirring, slowly drip 3,4,5-trifluorobenzoyl chloride (21.40g, 0.11mol) is after dropwising, be warming up to room temperature, TLC follows the tracks of reaction, and (reaction times is about 1 hour, silica-gel plate, ethyl acetate: sherwood oil=1: 1 (v/v)) to terminal, add ammonium chloride (5.30g, 0.1mol), behind the stirring 0.5h, petroleum ether extraction (30ml * 3), merge organic phase, behind the anhydrous magnesium sulfate drying, underpressure distillation obtains light yellow oil 20.37g, structure is suc as formula shown in the IX-3, productive rate 82.8%;
1H-NMR(400Hz，CDCl
3)：δ＝1.25-1.29(t，3H)，3.51(s，2H)，4.07-4.13(m，2H)，7.25-7.27(d，2H)；
13C-NMR：δ＝14.1，48.2，61.0，110.8，134.5，144.7，160.4，168.9，190.1；MS：M
+＝246.2。
(2) compound (13.00g, 0.053mol), K shown in the formula IX-3
2CO
3(7.61g, 0.055mol) be suspended in the 100ml ethanolic soln reflux 24h with ethyl bromoacetate (9.00g, 0.054mol), then cool to room temperature, filter out solid matter, and use the washing with alcohol solid, merge ethanolic soln, underpressure distillation, obtain colorless oil 13.91g, structure is suc as formula shown in the X-3, productive rate 79.5%.
1H-NMR(400Hz，CDCl
3)：δ＝1.21-1.27(m，6H)，3.11-3.17(m，2H)，4.08-4.14(m，4H)，4.43-4.47(t，1H)，7.28-7.34(m，2H)；
13C-NMR：δ＝14.1.35.2，49.1，61.3，110.8，135.5，144.5，159.5，169.9，173.1，195.2；MS：M
+＝332.1。
(3) compound (13.31g shown in the formula X-3,0.04mol) and ammonium acetate (12.32g, the 0.16mol) 20h that in 50ml acetic acid, refluxes, then reactant is poured in the 200ml frozen water, a large amount of solids are separated out again at once, filter, use the frozen water washing leaching cake, after the drying, use the methylene dichloride recrystallization, obtain the 9.12g solid, structure is suc as formula shown in the II-3, productive rate 80.5%.
1H-NMR(400Hz，CDCl
3)：δ＝1.22-1.26(t，3H)，2.87(s，2H)，4.11-4.17(m，2H)，7.17-7.23(m，2H)，9.21(br?s，1H)；
13C-NMR：δ＝14.7，61.7，42.7，101.2，108.4，133.8，139.4，144.8，167.7，180.1；MS：M
+＝285.1；mp：216-218℃。
(4) under nitrogen protection, sodium Metal 99.5 (0.92g, 0.04mol) is joined in the 30ml tertiary amyl alcohol, then add the FeCl of catalytic amount
3, reflux, sodium reacts complete behind the 2h, adds penta fluoro benzene nitrile (3.86g, 0.02mol), and compound shown in the formula II-3 (5.71g, 0.02mol) is dissolved in the 20ml tertiary amyl alcohol, slowly is added drop-wise in the mentioned solution, and 2h dropwises.Then under reflux state, keep 5h.Reaction solution is cooled to 60 ℃, adds the mixing solutions 50ml that is comprised of methyl alcohol, water and acetic acid, and behind the stirring at room 2h, backflow 2h filters, and methyl alcohol and water washing filter cake with hot obtain gold-tinted red solid 6.40g, and structure is suc as formula shown in the I-5, productive rate 73.9%.
Claims (4)
1. fluorine-containing Isosorbide-5-Nitrae-diketone pyrroles [3,4-C] and pyrrole derivative, its structure is suc as formula shown in the I:
Among the formula I, A and B independently are selected from respectively: a kind of in the group shown in group shown in phenyl, xenyl, the formula V or the formula VI, and have at least one to be group shown in formula V or the VI among A and the B:
Wherein: n is 1～5 integer; P is that 0～5 integer, q are 0～4 integer, and p and q are not zero simultaneously; Curves mark place is the position of substitution.
2. fluorine-containing Isosorbide-5-Nitrae as claimed in claim 1-diketone pyrroles [3,4-C] and pyrrole derivative is characterized in that, described fluorine-containing Isosorbide-5-Nitrae-diketone pyrroles [3,4-C] and pyrrole derivative are compound shown in formula I-4 or the formula I-5:
3. one kind prepares as claimed in claim 1 or 2 fluorine-containing 1,4-diketone pyrroles [3,4-C] and the method for pyrrole derivative, it is characterized in that, the key step of described method is: having under the rare gas element existence condition, refluxed at least 6 hours in the tertiary amyl alcohol solution of sodium tert-amyl alcohol by compound shown in the formula II and BCN, then after protonated, filtration, washing leaching cake and drying, obtain target compound successively;
Among the formula II, R is C
1～C
6The straight or branched alkyl, the definition of A and B is with identical described in claim 1 or 2.
4. method as claimed in claim 3 is characterized in that, described method specifically comprises the steps:
(1) under 0 ℃, in the NaOH solution of compound shown in the formula VIII, drip compound shown in the formula VII, dropwise, kept at least 1 hour at room temperature state, add again ammonium chloride, stir after at least 0.5 hour, obtain compound shown in the formula IX through extraction, drying and underpressure distillation successively;
(2) under alkaline condition, in the ethanolic soln of compound shown in the formula IX, drip ethyl bromoacetate, reflux after at least 24 hours, filter out solid inorganic alkali or salt, and use the washing with alcohol inorganic salt, and filtrate desolventizes through steaming, and underpressure distillation obtains compound shown in the formula X;
(3) compound shown in the formula X and ammonium acetate were refluxed 20 hours in acetic acid at least, reaction solution is poured in the frozen water, filters, and washing leaching cake, filter cake obtain compound shown in the formula II after with the methylene dichloride recrystallization;
(4) having under the rare gas element existence condition, compound shown in the formula II and BCN were refluxed 6 hours in the tertiary amyl alcohol solution of sodium tert-amyl alcohol at least, then the gained reaction solution is joined in the mixing solutions that is comprised of methyl alcohol, water and acetic acid, filter, and washing leaching cake, obtain target compound after the drying.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1231167A (en) * | 1998-03-27 | 1999-10-13 | 莱雅公司 | Cosmitis compositions containing novel pigment |
| CN1297450A (en) * | 1998-04-22 | 2001-05-30 | 西巴特殊化学品控股有限公司 | Preparation of alkylthio- and/or arylthio-substd. diketo-diaryl-pyrrolopyrroles |
| WO2004007604A1 (en) * | 2002-07-17 | 2004-01-22 | Ciba Specialty Chemicals Holding Inc. | High-molecular-weight polymeric material comprising diketopyrrolopyrrole pigments |
| CN1749327A (en) * | 2005-09-28 | 2006-03-22 | 华东理工大学 | Process for preparing DPP pigment |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1231167A (en) * | 1998-03-27 | 1999-10-13 | 莱雅公司 | Cosmitis compositions containing novel pigment |
| CN1297450A (en) * | 1998-04-22 | 2001-05-30 | 西巴特殊化学品控股有限公司 | Preparation of alkylthio- and/or arylthio-substd. diketo-diaryl-pyrrolopyrroles |
| WO2004007604A1 (en) * | 2002-07-17 | 2004-01-22 | Ciba Specialty Chemicals Holding Inc. | High-molecular-weight polymeric material comprising diketopyrrolopyrrole pigments |
| CN1749327A (en) * | 2005-09-28 | 2006-03-22 | 华东理工大学 | Process for preparing DPP pigment |
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