CN102344418A - Alkyne-containing quinoxalin derivative and preparation method thereof - Google Patents
Alkyne-containing quinoxalin derivative and preparation method thereof Download PDFInfo
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Abstract
The invention discloses an alkyne-containing quinoxalin derivative and a preparation method thereof. The structure general formula of the alkyne-containing quinoxalin derivative is shown in the specifications, wherein R is aryl, alkyl, trimethylsilyl or halogen alkyl; and R' is hydrogen, halogen, aryl or alkyl. The preparation method comprises the following steps of: putting terminal alkyne and an o-phenylenediamine compound serving as raw materials and CuX serving as a catalyst into a sealed pipe; reacting with magnetic stirring to obtain a crude product; and performing silica gel column chromatography to obtain the alkyne-containing quinoxalin derivative. Compared with the prior art, the invention has the advantages: the raw materials of the product are cheap and readily-available, and the method is easy to operate and control and has mild reaction conditions, high efficiency and low environmental pollution.
Description
Technical field
The present invention relates to quinoxaline derivatives, be specifically related to contain alkynes quinoxaline derivatives and preparation method thereof.
Background technology
Pyrazine and phenyl ring thick and benzopyrazines claim quinoxaline (quinoxaline) again, the precedence numbering of its structural formula and each atom as follows:
The classical synthesis method of quinoxaline derivatives is through O-Phenylene Diamine and 1, and the condensation reaction of 2-diketone obtains, and this speed of response is fast, the product well-crystallized.If use pyrocatechol and quadrol to be raw material, also can first condensation, get quinoxaline through dehydrogenation again.
In recent years, researcher has been obtained some new developments in synthesizing of quinoxaline, as:
(1) Chandrasekhar S. group utilizes PdCl
2/ CuCl
2Catalyst system becomes corresponding 1 with oxidizing alkyne; The 2-dione compounds; This intermediate is separated purification; Synthesized substituted quinoxaline derivatives (Chandrasekhar S with O-Phenylene Diamine compounds one kettle way then; Kesava R.N, Praveen K.V.Oxidation of alkynes using PdCl
2/ CuCl
2In PEG as a recyclable catalytic system:one-pot synthesis of quinoxalines.Tetrahedron Lett.2010,51,3623-3625.).
(2) Swaminathan M. research group has developed a kind of new catalyst system TiO
2-P25-SO
4 2-, with O-Phenylene Diamine and 1, the 2-diketone is approach efficiently (Krishnakumar B, the Swaminathan M.A recyclable and highly effectivesulfated TiO of raw material synthesizing quinoxaline derivant
2-P25for the synthesis of quinoxaline and dipyridophenazine derivatives at room temperature.Journal of Organometallic Chemistry.2010,695,2572-2577.).
(3) Laetitia J.M. etc. has found a kind of novel method that obtains quinoxaline derivatives.The diazotization carbonyl compound that is obtained by acyl chloride reaction in the novel method need not separated as intermediate; Directly can obtain target compound (Laetitia J.M with the O-Phenylene Diamine reaction; Marzinzik A.L.Safe and Reliable Synthesis of Diazoketones and Quinoxalines in a Continuous Flow Reactor.Organic Lett.2011; 13,320-323.).
Also not seeing at present has with terminal alkyne and O-Phenylene Diamine compounds as raw material, is catalysts with CuX, the report of synthesizing quinoxaline derivant.
Summary of the invention
The technical problem that the present invention will solve provides a kind of alkynes quinoxaline derivatives and preparation method thereof that contains.Products material of the present invention is cheap and easy to get, and method is simple to operate, and reaction conditions is gentle, and is low in the pollution of the environment.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
Contain the alkynes quinoxaline derivatives, its general structure is as shown in the formula shown in (I):
Wherein:
R is aromatic base, alkyl, trimethyl silicon based or halogen alkyl; Aromatic base wherein can be phenyl, alkyl phenyl, bromophenyl, fluorophenyl, chloro-phenyl-, alkoxyl phenyl, thienyl, pyridyl or naphthyl etc., and described alkyl can be hexyl, butyl, propyl group or the tertiary butyl etc.;
R ' is hydrogen, halogen, aromatic base or alkyl; Aromatic base wherein can be phenyl, alkyl phenyl, bromophenyl, fluorophenyl, chloro-phenyl-, alkoxyl phenyl, thienyl, pyridyl or naphthyl etc., and described alkyl can be hexyl, butyl, propyl group or the tertiary butyl etc.
Described R ' is hydrogen or chlorine preferably.
The alkynes quinoxaline derivatives that contains of the present invention comprises following compounds:
(a) 2-(4-ethylbenzene base)-3-(2-(4-ethylbenzene base) ethynyl) quinoxaline;
(b) 2-hexyl-3-(1-octyne base) quinoxaline;
(c) 6-chloro-2-phenyl-3-(2-phenylacetylene base) quinoxaline;
(d) 2-(4-tolyl)-3-(2-(4-tolyl) ethynyl) quinoxaline;
(e) 2-(4-fluorophenyl)-3-(2-(4-fluorophenyl) ethynyl) quinoxaline.
The above-mentioned preparation method who contains the alkynes quinoxaline derivatives is to be raw material with terminal alkyne and O-Phenylene Diamine compounds, is that catalyzer places in the tube sealing with CuX, and reaction obtains crude product under magnetic agitation, obtains through silica gel column chromatography then.
Concrete preparation method is: the mol ratio by 1: 3～7 takes by weighing terminal alkyne and the O-Phenylene Diamine compounds places in the tube sealing; Add the Catalysts Cu X that is equivalent to 0.05～0.3 times of terminal alkyne amount of substance; Reaction is until reacting completely under the magnetic agitation; Filter; Filtrating is used an amount of acetic acid ethyl dissolution; Extraction; Ethyl acetate is removed in decompression behind the organic layer anhydrous sodium sulfate drying; Silica gel column chromatography on the gained crude product; Mixing solutions with sherwood oil and ethyl acetate is the eluent wash-out; The elutriant solvent evaporated promptly gets and contains the alkynes quinoxaline derivatives accordingly.
In order further to reduce the generation of side reaction; The following method preparation of preferred employing contains the preparation method of alkynes quinoxaline derivant: the mol ratio by 1: 3～7 takes by weighing terminal alkyne and the o-phenylenediamine compounds places in the tube sealing; Add the Catalysts Cu X and the proper amount of solvent that are equivalent to 0.05～0.3 times of terminal alkyne amount of substance; Reaction is until reacting completely under the magnetic agitation; Filter; The filtrate decompression distillation is revolved and is desolventized; An amount of acetic acid ethyl dissolution of residue; Extraction; Organic layer with anhydrous sodium sulfate drying after decompression remove ethyl acetate; Silica gel column chromatography on the gained crude product; Mixed solution with benzinum and ethyl acetate is the eluant, eluent wash-out; The eluent solvent evaporated promptly gets and contains the alkynes quinoxaline derivant accordingly.Wherein, described solvent can be chlorobenzene, methylene dichloride, 1,2-ethylene dichloride, toluene or tetrahydrofuran (THF) etc., and the add-on of solvent is to be enough to cover the reactant that will participate in reaction in the tube sealing.
Among the above-mentioned preparation method:
The mol ratio of said terminal alkyne and O-Phenylene Diamine compounds is preferably 1: 3～and 5.
Described Catalysts Cu X is CuCl, CuBr or CuI.The add-on of said catalyzer is preferably 0.1～0.2 times of terminal alkyne amount of substance; When the add-on of catalyzer during greater than 0.3 times of terminal alkyne amount of substance; Reaction can be carried out equally, and just the excessive use of catalyzer can improve production cost and increase the burden of postorder purification step.
Described terminal alkyne can be phenylacetylene, 4-methylbenzene acetylene, 4-anisole acetylene, 3-methylbenzene acetylene, 1-octyne, 1-pentyne, 3-chloroallylene, 5-chloro-1-pentyne or encircle third acetylene etc.; Described O-Phenylene Diamine compounds can be O-Phenylene Diamine, 4-chlorine O-Phenylene Diamine, 4-nitro O-Phenylene Diamine, 4,5-dichloro O-Phenylene Diamine or 4,5-dimethyl O-Phenylene Diamine etc.
The volume ratio of said eluent PetroChina Company Limited.'s ether and ethyl acetate is 30～60: 1.
In the process of said extraction, can be Xian Jiashui, and then add saturated aqueous common salt and carry out, mainly be in order to remove some excessive reactant.
Above-mentioned reaction is generally carried out under 0～100 ℃ of condition, preferably carries out at 40～70 ℃.
Judge whether reaction is complete in the aforesaid method, can adopt TLC to follow the tracks of the process of reaction, stop promptly to represent reacting completely until reaction.Test by the applicant learns that reaction generally promptly stops at 4～24h.
Compared with prior art, the invention provides a class formation novel contain the alkynes quinoxaline derivatives, use therein low in raw material cost is easy to get; Said preparation contains the easy control simple to operate of alkynes quinoxaline derivatives method, and reaction conditions is gentle, efficient, low in the pollution of the environment; Further, in reaction, add solvent the main reaction transformation efficiency is reached more than 90%, reduced the generation of side reaction effectively.
Embodiment
The preparing method's who contains the alkynes quinoxaline derivatives according to the invention general formula is following:
Wherein:
R be aromatic base (for example: phenyl, alkyl phenyl, bromophenyl, fluorophenyl, chloro-phenyl-, alkoxyl phenyl, thienyl, pyridyl, naphthyl etc.), alkyl (for example: hexyl, butyl, propyl group, the tertiary butyl etc.) or other groups (for example: trimethyl silicon based, halogen alkyl etc.).
R ' is hydrogen, halogen, aromatic base (for example: phenyl, alkyl phenyl, bromophenyl, fluorophenyl, chloro-phenyl-, alkoxyl phenyl, thienyl, pyridyl, naphthyl etc.) or alkyl (for example: hexyl, butyl, propyl group, the tertiary butyl etc.).
CuX is CuCl, CuBr or CuI.
With concrete embodiment the present invention is further specified below, but the present invention is not limited to these embodiment.
The preparation and the structural characterization of embodiment 1:2-(4-ethylbenzene base)-3-(2-(4-ethylbenzene base) ethynyl) quinoxaline (a)
In tube sealing, add ethylbenzene acetylene 1mmol and O-Phenylene Diamine 5mmol; Add 0.2mmol Catalysts Cu Cl and solvent chlorobenzene 2ml; In 70 ℃ oil bath, reacted 10 hours under the magnetic agitation; Filter; Filtrating is revolved through underpressure distillation and is desolventized, residuum with the 10mL acetic acid ethyl dissolution after more successively water (3 * 2mL), saturated aqueous common salt (2mL) washing, organic layer with anhydrous sodium sulfate drying after again decompression remove ethyl acetate; Silica gel column chromatography on the gained crude product is with eluent (V
Sherwood oil: V
Ethyl acetate=60: 1) wash-out, the elutriant solvent evaporated, the gained yellow oil is compound a.Its hydrogen spectrum, carbon spectrum and structural formula are following:
1HNMR(500MHz，CDCl
3)δ8.15-8.09(m，2H)，8.06(d，J＝8.0Hz，2H)，7.75(dd，J＝6.2，3.2Hz，2H)，7.44(d，J＝8.0Hz，2H)，7.39(d，J＝7.9Hz，2H)，7.19(d，J＝7.8Hz，2H)，2.78(q，J＝7.5Hz，2H)，2.66(q，J＝7.6Hz，2H)，1.32(t，J＝7.6Hz，3H)，1.24(t，J＝7.6Hz，3H).
13C?NMR(125MHz，CDCl
3)δ155.0，146.2，146.1，140.9，140.7，138.3，135.1，132.1，130.4，129.9，129.7，129.2，128.7，128.0，127.6，119.0，95.4，88.2，28.9，28.8，15.6，15.0.
The preparation and the structural characterization of embodiment 2:2-hexyl-3-(1-octyne base) quinoxaline (b)
In tube sealing, add 1-octyne 1mmol and O-Phenylene Diamine 3mmol; Add catalyzer 0.3mmolCuI; In 90 ℃ water-bath, reacted 16 hours under the magnetic agitation; Filter; Filtrating with behind the 10mL acetic acid ethyl dissolution more respectively water (3 * 2mL), saturated aqueous common salt (2mL) washs; Reduce pressure behind the anhydrous sodium sulfate drying again and remove ethyl acetate, silica gel column chromatography on the gained crude product is with eluent (V
Sherwood oil: V
Ethyl acetate=50: 1) wash-out, the elutriant solvent evaporated, gained red-brown oily matter is compound b.Its hydrogen spectrum, carbon spectrum and structural formula are following:
1H?NMR(500MHz，CDCl
3)δ8.05-7.95(m，2H)，7.68(m，2H)，3.20-3.10(t，J＝5.0Hz，2H)，2.56(t，J＝7.1Hz，2H)，1.85(m，2H)，1.76-1.59(m，2H)，1.56-1.41(m，4H)，1.41-1.29(m，8H)，0.91(t，J＝5.0Hz，3H)，0.90(t，J＝6.7Hz，3H).
13C?NMR(125MHz，CDCl
3)δ158.9，140.9，140.7，140.1，130.0，129.3，128.8，128.6，97.6，78.9，36.6，31.8，31.5，29.8，29.5，28.9，28.8，28.4，22.70，22.69，19.9，14.2.
The preparation and the structural characterization of embodiment 3:6-chloro-2-phenyl-3-(2-phenylacetylene base) quinoxaline (c)
In tube sealing, add phenylacetylene 1mmol and to chlorine O-Phenylene Diamine 5mmol; Add catalyzer 0.2mmolCuCl and methylene chloride 2ml; Room temperature lower magnetic force stirring reaction 10 hours; Filter; Filtrating is revolved through underpressure distillation and is desolventized, residuum with the 10mL acetic acid ethyl dissolution after more respectively water (3 * 2mL), saturated aqueous common salt (2mL) washing, behind the anhydrous sodium sulfate drying again decompression remove ethyl acetate; Silica gel column chromatography on the gained crude product is with eluent (V
Sherwood oil: V
Ethyl acetate=30: 1) wash-out, the elutriant solvent evaporated, gained light brown solid is compound c.Its hydrogen spectrum, carbon spectrum and structural formula are following:
1H?NMR(500MHz，CDCl3)δ8.13-8.09(m，4H)，7.71(dd，J＝8.9，2.2Hz，1H)，7.56-7.58(m，3H)，7.50-7.48(m，2H)，7.42-7.34(m，3H).
13C?NMR(125MHz，CDCl3)δ155.4，141.4，139.40，139.15，137.5，136.3，132.4，131.7，130.67，130.05，129.96，129.82，128.66，128.35，127.7，121.7，96.1，88.3.
The preparation and the structural characterization of embodiment 4:2-(4-tolyl)-3-(2-(4-tolyl) ethynyl) quinoxaline (d)
In tube sealing, add methylbenzene acetylene 1mmol and O-Phenylene Diamine 4mmol; Add catalyzer 0.2mmol CuI and solvent 1; 2-ethylene dichloride 2ml; In 40 ℃ oil bath, reacted 12 hours under the magnetic agitation, filter, filtrating is revolved through underpressure distillation and is desolventized; Residuum with the 10mL acetic acid ethyl dissolution after more respectively water (3 * 2mL), saturated aqueous common salt (2mL) washing; Reduce pressure behind the anhydrous sodium sulfate drying again and remove ethyl acetate, silica gel column chromatography on the gained crude product is with eluent (V
Sherwood oil: V
Ethyl acetate=60: 1) wash-out, the elutriant solvent evaporated, the gained yellow oil is compound d.Its hydrogen spectrum, carbon spectrum and structural formula are following:
1H?NMR(500MHz，CDCl
3)δ8.12(m，2H)，8.05(d，J＝8.0Hz，2H)，7.75(dd，J＝6.3，3.4Hz，2H)，7.42(d，J＝7.9Hz，2H)，7.37(d，J＝7.8Hz，2H)，7.17(d，J＝7.8Hz，2H)，2.48(s，3H)，2.37(s，3H).
13C?NMR(126MHz，CDCl3)δ154.9，140.9，140.7，139.96，139.78，138.2，134.9，132.0，130.4，129.98，129.65，129.2，128.8，128.68，127.4，118.8，95.3，88.2，21.60，21.44.
The preparation and the structural characterization of embodiment 5:2-(4-fluorophenyl)-3-(2-(4-fluorophenyl) ethynyl) quinoxaline (e)
In tube sealing, add fluorobenzene acetylene 1mmol and O-Phenylene Diamine 4mmol; Add catalyzer 0.1mmolCuBr and methylene chloride 2ml; 0 ℃ of condition lower magnetic force stirring reaction 6 hours; Filter; Filtrating is revolved through underpressure distillation and is desolventized, residuum with the 10mL acetic acid ethyl dissolution after more respectively water (3 * 2mL), saturated aqueous common salt (2mL) washing, behind the anhydrous sodium sulfate drying again decompression remove ethyl acetate; Silica gel column chromatography on the gained crude product is with eluent (V
Sherwood oil: V
Ethyl acetate=40: 1) wash-out, the elutriant solvent evaporated, the gained white needle-like crystals is Verbindung.Its hydrogen spectrum, carbon spectrum and structural formula are following:
1H?NMR(500MHz，CDCl3)δ8.12(m，4H)，7.79(m，2H)，7.49(dd，J＝8.7，5.4Hz，2H)，7.26(d，J＝8.0Hz，3H)，7.07(m，2H).
13C?NMR(126MHz，CDCl3)δ164.84，164.37，153.86，141.03，140.70，137.70，134.20，134.13，133.75，131.77，131.71，130.87，130.45，129.55，129.27，128.77，116.12，115.94，115.33，115.16，94.05，87.98.
The synthetic following compound, specific as follows stating shown in the table 1 of obtaining of the preparation method of similar the foregoing description 1:
Table 1: contain the alkynes quinoxaline derivatives
| NO. | R | R’ |
| 1 | Phenyl | H |
| 2 | The n-propyl phenyl | H |
| 3 | To bromophenyl | H |
| 4 | The 3-aminomethyl phenyl | H |
| 5 | Chloropropyl | H |
| 6 | Thienyl | H |
| 7 | Phenyl | 4, the 5-dichloro |
| 8 | Phenyl | Nitro |
| 9 | Phenyl | Methoxyl group |
| 10 | Phenyl | 4, the 5-dimethyl |
| 11 | Trimethyl silicon based | H |
| 12 | N-propyl | H |
Claims (10)
1. contain the alkynes quinoxaline derivatives, its general structure is as shown in the formula shown in (I):
Wherein:
R is aromatic base, alkyl, trimethyl silicon based or halogen alkyl;
R ' is hydrogen, halogen, aromatic base or alkyl.
2. the alkynes quinoxaline derivatives that contains according to claim 1 is characterized in that: R ' is hydrogen or chlorine.
3. the alkynes quinoxaline derivatives that contains according to claim 1 is characterized in that it comprises following compounds:
(a) 2-(4-ethylbenzene base)-3-(2-(4-ethylbenzene base) ethynyl) quinoxaline;
(b) 2-hexyl-3-(1-octyne base) quinoxaline;
(c) 6-chloro-2-phenyl-3-(2-phenylacetylene base) quinoxaline;
(d) 2-(4-tolyl)-3-(2-(4-tolyl) ethynyl) quinoxaline;
(e) 2-(4-fluorophenyl)-3-(2-(4-fluorophenyl) ethynyl) quinoxaline.
4. the said preparation method who contains the alkynes quinoxaline derivatives of claim 1; It is characterized in that: it is to be raw material with terminal alkyne and O-Phenylene Diamine compounds; With CuX is that catalyzer places in the tube sealing, and reaction obtains crude product under magnetic agitation, obtains through silica gel column chromatography then.
5. the preparation method who contains the alkynes quinoxaline derivant according to claim 4; It is characterized in that: the mol ratio by 1: 3～7 takes by weighing terminal alkyne and the o-phenylenediamine compounds places in the tube sealing; Add the Catalysts Cu X that is equivalent to 0.05～0.3 times of terminal alkyne amount of substance; Reaction is until reacting completely under the magnetic agitation; Filter; Filtrating is used an amount of acetic acid ethyl dissolution; Extraction; Organic layer with anhydrous sodium sulfate drying after decompression remove ethyl acetate; Silica gel column chromatography on the gained crude product; Mixed solution with benzinum and ethyl acetate is the eluant, eluent wash-out, and the eluent solvent evaporated promptly gets and contains the alkynes quinoxaline derivant accordingly.
6. the preparation method who contains the alkynes quinoxaline derivant according to claim 5; It is characterized in that: the mol ratio by 1: 3～7 takes by weighing terminal alkyne and the o-phenylenediamine compounds places in the tube sealing; Add the Catalysts Cu X and the proper amount of solvent that are equivalent to 0.05～0.3 times of terminal alkyne amount of substance; Reaction is until reacting completely under the magnetic agitation; Filter; The filtrate decompression distillation is revolved and is desolventized; An amount of acetic acid ethyl dissolution of residue; Extraction; Organic layer with anhydrous sodium sulfate drying after decompression remove ethyl acetate; Silica gel column chromatography on the gained crude product; Mixed solution with benzinum and ethyl acetate is the eluant, eluent wash-out; The eluent solvent evaporated promptly gets and contains the alkynes quinoxaline derivant accordingly.
7. the preparation method who contains the alkynes quinoxaline derivatives according to claim 6; It is characterized in that: described solvent is chlorobenzene, methylene dichloride, 1; 2-ethylene dichloride, toluene or tetrahydrofuran (THF), the add-on of solvent are to be enough to cover the reactant that will participate in reaction in the tube sealing.
8. according to each described preparation method who contains the alkynes quinoxaline derivatives in the claim 4～7, it is characterized in that: described Catalysts Cu X is CuCl, CuBr or CuI.
9. according to each described preparation method who contains the alkynes quinoxaline derivatives in the claim 4～7, it is characterized in that: described terminal alkyne is phenylacetylene, 4-methylbenzene acetylene, 4-anisole acetylene, 3-methylbenzene acetylene, 1-octyne, 1-pentyne, 3-chloroallylene, 5-chloro-1-pentyne or encircles third acetylene;
Described O-Phenylene Diamine compounds is O-Phenylene Diamine, 4-chlorine O-Phenylene Diamine, 4-nitro O-Phenylene Diamine, 4,5-dichloro O-Phenylene Diamine or 4,5-dimethyl O-Phenylene Diamine.
10. according to each described preparation method who contains the alkynes quinoxaline derivatives in the claim 4～7, it is characterized in that: the volume ratio of said eluent PetroChina Company Limited.'s ether and ethyl acetate is 30～60: 1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496966A (en) * | 2014-12-24 | 2015-04-08 | 广西师范大学 | Method for synthesizing quinoxaline-triazole compounds from o-phenylenediamine, phenylacetylene and nitrine |
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|---|---|---|---|---|
| US5583227A (en) * | 1994-06-03 | 1996-12-10 | Mochida Pharmaceutical Co. Ltd. | Antiulcer compounds having a substituted alkynyl or quinoxaline nucleus and methods of making thereof |
| CN1966500A (en) * | 2005-11-17 | 2007-05-23 | 中国科学院上海药物研究所 | Quinoxaline derivative, preparation method and uses |
-
2011
- 2011-08-17 CN CN2011102360309A patent/CN102344418A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5583227A (en) * | 1994-06-03 | 1996-12-10 | Mochida Pharmaceutical Co. Ltd. | Antiulcer compounds having a substituted alkynyl or quinoxaline nucleus and methods of making thereof |
| CN1966500A (en) * | 2005-11-17 | 2007-05-23 | 中国科学院上海药物研究所 | Quinoxaline derivative, preparation method and uses |
Non-Patent Citations (1)
| Title |
|---|
| WANG W. ET AL: "Copper-Catalyzed Synthesis of Quinoxalines with o-Phenylenediamine and Terminal Alkyne in the Presence of Bases", 《ORG. LETT.》, vol. 13, no. 17, 1 August 2011 (2011-08-01), pages 4514 - 4517 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496966A (en) * | 2014-12-24 | 2015-04-08 | 广西师范大学 | Method for synthesizing quinoxaline-triazole compounds from o-phenylenediamine, phenylacetylene and nitrine |
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Application publication date: 20120208 |