CN104844509A - Mild-condition and metal-free method for preparing aminoquinoline derivatives - Google Patents
Mild-condition and metal-free method for preparing aminoquinoline derivatives Download PDFInfo
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- CN104844509A CN104844509A CN201410050717.7A CN201410050717A CN104844509A CN 104844509 A CN104844509 A CN 104844509A CN 201410050717 A CN201410050717 A CN 201410050717A CN 104844509 A CN104844509 A CN 104844509A
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- Prior art keywords
- quinoline
- phosphorous acid
- acid ester
- preparation
- amido
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a method for preparing aminoquinoline derivatives (I) and (II), and belongs to the field of organic chemistry. Substituted quinoline oxide (or isoquinoline oxide) and tertiary amine (or secondary amine) are taken as raw materials, in the presence of phosphite and carbon tetrachloride, to prepare the aminoquinoline derivatives (I) and (II). The raw materials are cheap and are easy to obtain; the reaction condition is mild; the operation is simple; the synthetic yield is high; and the method is beneficial for industrial production. The derivatives have potential application to the fields of chemistry and medicine. The invention provides a novel way for compounding the aminoquinoline derivatives.
Description
Technical field
The present invention relates to a kind of mild condition and the preparation method of amido quinoline without metal superlattice, belong to organic chemistry filed.
Background technology
Heterogeneous ring compound is the important integral part of organic chemistry, and be the very important organic compound of a class, it has a wide range of applications in all many-sides such as biochemical industry, daily use chemicals, medicine, materials.Quinolines is the heterocycle compound with pharmacologically actives such as antibacterial, anti-malarials.Through years of researches, quinoline antimalarial agent has a great development, and wherein quinolylamine and derivative thereof are important component parts wherein.Many medicines with quinolylamine ring are to healing abalienation, antibacterial, anti-inflammatory, hypertension, antidepressant, anti-malarial (J. Med. Chem. 2001,44,3187-3194) all have biological activity and pharmacologically active, some is applied clinically.Recent study shows, N, N-di alkylamino group quinoline has anticancer, antitumor and antioxygenation (J. Med. Chem., 1989,32,1295-1300; Eur. J. Biol. Sci., 2009,1,32-36).
At present, the synthesis of amido quinoline is mostly by traditional method.In inert solvent, 2-amido quinoline is obtained by reacting at liquefied ammonia, tertiary amine by amido highly basic and quinoline.Amido lithium and quinoline react and generate N-methylamino quinoline (J. Org. Chem., 1946,11,239-246) in ether and nitrogen atmosphere.2-chloroquinoline and diethylamine reflux and obtain diethylin quinoline hydrochloride (Ann. Inst. Paslsur, 1930,44,719) in benzene.2-chloroquinoline and the backflow of excessive secondary amine, then use Na
2cO
3neutralization reaction obtains a series of 2-amido quinoline (J. Am. Chem. Soc., 1948,71,1109-1110).2-chloroquinoline and tertiary amine react at 100 DEG C can generate N in 4 days, N-di alkylamino group quinoline (J. Chem. Soc., Chem. Commun., 1991,306-307).It is numerous and diverse to there is step in the method that these tradition prepare 2-(N, N-dialkyl amino) quinolines, severe reaction conditions, as highly basic used by needs, or toxic reagent, or higher temperature, or the long time, agents useful for same is difficult to preserve and the shortcoming such as expensive.Therefore, simple in the urgent need to finding a kind of step, reaction conditions is gentle; regioselectivity is high; the synthetic method of the amido quinoline that yield is high, this will promote the exploitation of amido quinoline, has great importance to the research and development of protection China independent intellectual property right.
Summary of the invention
Based on above-mentioned research background, the object of the present invention is to provide a kind of mild condition, regioselectivity is high, the new synthetic method of what yield was high be obtained by reacting amido quinoline.
For realizing the object of the invention, the present invention, to replace oxidation quinoline (or replace isoquinoline) with tertiary amine (or secondary amine) for raw material, synthesizes amido quinoline under phosphorous acid ester and tetracol phenixin effect.The following general formula I of amido quinoline of the present invention and II.
Wherein R
1represent the monosubstituted of one of following group: hydrogen base, nitro, amino, kharophen, cyano group, C1-3 alkyl, C1-3 alkoxyl group, halogen (-F ,-Cl ,-Br and-I), preferably-H ,-NO
2,-Br ,-CH
3,-OCH
3deng; R
2represent the monosubstituted of one of following group: C1-4 alkyl; R
3represent the monosubstituted of one of following group: C1-4 alkyl; Preferred R
2and R
3be all-CH mutually
3,-C
2h
5,-CH
2cH
2cH
3,-CH
2cH
2cH
2cH
3deng group.
The salt of Compound I and II is pharmaceutically acceptable salt.As more satisfactory salt, it can with the salt of mineral acid, example hydrochloric acid salt, vitriol or similar salt, also can be the salt with organic acidic group, as metilsulfate and similar salt.
Concrete technical scheme realizes as follows: first dissolved in a suitable solvent with tertiary amine (or secondary amine) by replacement oxidation quinoline (or replacing isoquinoline), then add phosphorous acid ester and tetracol phenixin, react at 0-60 DEG C.After reaction terminates, through extraction, dry, pressure reducing and steaming solvent, obtains general formula (I) (or (II)) amido quinoline crude product.
Replace oxidation quinoline (replacement isoquinoline): tertiary amine (secondary amine): phosphorous acid ester: the ratio of tetracol phenixin is preferably 1 (mmol): 3 (mmol): 2 (mmol): 0.5 (mL).
Solvent is chosen as one or more in THF, acetonitrile, toluene, dioxane, DMSO and ethanol as solvent, and preferred THF is solvent.
Phosphorous acid ester is dimethoxy phosphorous acid ester, diethoxy phosphorous acid ester, two positive propoxy phosphorous acid esters, diisopropoxy phosphorous acid ester, two phenoxy group phosphorous acid esters and benzyloxy phosphorous acid ester, preferred diisopropoxy phosphorous acid ester.Preferred employing room temperature 20 DEG C is best temperature of reaction.
Reaction formula is as follows:
R in formula
1, R
2and R
3state the same, R
4for H, or and R
2, R
3identical.
Abstraction and purification amido quinoline crude product, such as, is undertaken being separated to obtain amido quinoline (I) or (II) by silica gel column chromatography by crude product, makes it obtain better application.
Agents useful for same of the present invention all commercially.
Beneficial effect of the present invention is: the synthetic method cheaper starting materials of amido quinoline of the present invention is easy to get, reaction conditions gentleness, non-metal catalyst, easy and simple to handle, regioselectivity is high, productive rate is high, be conducive to suitability for industrialized production, provides a new approach for preparation has amido quinoline that is antibacterial, anti-malarial isoreactivity.
Embodiment
Below by embodiment, the present invention will be further elaborated, but and do not mean that content limitation of the present invention is in embodiment.
the synthesis of oxidation quinoline:
Take quinoline 3.87 g(30 mmol) join in the glacial acetic acid of 30 mL, then add the hydrogen peroxide (30%) of 4.2 mL, and airtight, stir 3 days at 70 DEG C.Thin layer analyses detection reaction process.React complete, revolve and steam solvent acetic acid and water, with saturated K
2cO
3solution adjust pH is to 8.Cross and filter precipitation, then use chloroform extraction 3 times (15 mL/ time), combined chloroform extraction liquid is also concentrated, and column chromatography for separation obtains light red solid 3.86 g (productive rate is 89%).
Other synthesis replacing oxidation quinoline or replacement isoquinoline derivative is the same.
embodiment 1:r
1=H, R
2=R
3=C
2h
5time, the preparation of 2-(N, N-diethyl) amido quinoline
Oxidation quinoline 0.145 g (1 mmol) is added in 50 mL round-bottomed flasks, triethylamine 0.42 mL (3 mmol), diisopropyl phosphite 0.332 g (2 mmol) and tetracol phenixin 0.5 mL, tetrahydrofuran (THF) 15 mL, stirred at ambient temperature, react 7 hours, along with the growth in reaction times, there is a large amount of white solids to generate, cross and filter precipitation, concentrated, column chromatography (V
etOAc: V
pE=1:4, v:v) be separated, obtain pale yellow oil.
Productive rate 83.0%;
1h NMR (400 MHz, CDCl
3)
δ: 1.26 (t, 6H ,-CH
3); 3.68 (m, 4H ,-C
h 2cH
3); 6.84 (d,
j=9.20 Hz, 1H, 3-H); 7.16 (m, 1H, 6-H); 7.51 (m, 1H, 7-H); 7.57 (dd,
j=1.20 Hz,
j=8.00 Hz, 1H, 5-H); 7.68 (d,
j=8.40 Hz, 1H, 8-H); 7.84 (d,
j=9.20 Hz, 1H, 4-H);
13c NMR (100 MHz, CDCl
3)
δ: 13.3 (-CH
2 ch
3); 42.4 (-N
ch
2-); 109.1 (C-3); 121.2 (C-6); 122.3 (C-10); 126.3 (C-5); 127.2 (C-8); 129.2 (C-7); 137.0 (C-4); 148.5 (C-9); 156.0 (C-2).
Embodiment 2:R
1=OCH
3, R
2=R
3=CH
2cH
2cH
3time, the preparation of 2-(N, N-diη-propyl) amido quinoline
6-methoxyl group oxidation quinoline 0.175 g (1 mmol) is added in 50 mL round-bottomed flasks, Tri-n-Propylamine 0.57 mL (3 mmol), diisopropyl phosphite 0.332 g (2 mmol) and tetracol phenixin 0.5 mL, tetrahydrofuran (THF) 15 mL, stirred at ambient temperature, react 7 hours, along with the growth in reaction times, there is a large amount of white solids to generate, cross and filter precipitation, concentrated, column chromatography (V
etOAc: V
pE=1:5, v:v) be separated, obtain pale yellow oil.
Productive rate 68.0%;
1h NMR (400 MHz, CDCl
3)
δ: 0.98 (t, 6H ,-C
h 3); 1.69 (m, 4H ,-C
h 2cH
3); 3.54 (m, 4H ,-C
h 2cH
2cH
3); 3.87 (s, 3H ,-OCH
3); 6.80 (d,
j=9.20 Hz, 1H, 5-H); 6.94 (d,
j=2.80 Hz, 1H, 5-H); 7.20 (dd,
j=2.80 Hz,
j=9.20 Hz, 1H, 7-H); 7.61 (d,
j=9.20 Hz, 1H, 4-H); 7.75 (d,
j=8.80 Hz, 1H, 8-H);
13c NMR (100 MHz, CDCl
3)
δ: 11.5 (-CH
2 ch
3); 21.1 (-
ch
2cH
3); 50.5 (-N
ch
2-); 55.5 (-O
ch
3); 106.1 (C-5); 109.5 (C-3); 120.7 (C-7); 122.4 (C-10); 127.8 (C-8); 136.0 (C-4); 144.0 (C-9); 154.2 (C-6); 155.4 (C-2).
Embodiment 3:R
1=OCH
3, R
2=R
3=CH
2cH
2cH
3time, the preparation of 2-(N, N-diη-propyl) amido quinoline
5-nitro oxidation quinoline 0.190 g (1 mmol) is added in 50 mL round-bottomed flasks, tri-n-butylamine 0.71 mL (3 mmol), diethyl phosphite 0.276 g (2 mmol) and tetracol phenixin 0.5 mL, tetrahydrofuran (THF) 15 mL, stirred at ambient temperature, react 7 hours, along with the growth in reaction times, there is a large amount of white solids to generate, cross and filter precipitation, concentrated, column chromatography (V
etOAc: V
pE=1:3, v:v) be separated, obtain pale yellow oil.
Productive rate 59.0%;
1h NMR (400 MHz, CDCl
3)
δ: 0.99 (t, 6H ,-C
h 3); 1.40 (m, 4H ,-C
h 2cH
3); 1.65 (m, 4H ,-C
h 2cH
2cH
3); 3.60 (m, 4H ,-C
h 2cH
2cH
2cH
3); 7.01 (d,
j=9.60 Hz, 1H, 3-H); 7.52 (t, 1H, 7-H); 7.90 (d,
j=8.00 Hz, 2H, 6,8-H); 8.61 (d,
j=10.00 Hz, 1H, 4-H);
13c NMR (100 MHz, CDCl
3)
δ: 14.0 (-CH
2 ch
3); 20.3 (-
ch
2cH
3); 30.0 (-
ch
2cH
2cH
3); 48.3 (-N
ch
2-); 112.1 (C-3); 114.8 (C-10); 118.7 (C-6); 127.2 (C-7); 132.3 (C-4); 133.1 (C-8); 145.8 (C-5); 149.3 (C-9); 156.3 (C-2).
Embodiment 4:R
1=H, R
2=R
3=C
2h
5time, the preparation of 1-(N, N-diethyl) amido isoquinoline 99.9
Isoquinoline 0.145 g (1 mmol) is added in 50 mL round-bottomed flasks, triethylamine 0.42 mL (3 mmol), di-n-propyl phosphite 0.332 g (2 mmol) and tetracol phenixin 0.5 mL, tetrahydrofuran (THF) 15 mL, stirred at ambient temperature, react 7 hours, along with the growth in reaction times, there is a large amount of white solids to generate, cross and filter precipitation, concentrated, column chromatography (V
etOAc: V
pE=1:4, v:v) be separated, obtain pale yellow oil.
Productive rate 78.0%;
1h NMR (400 MHz, CDCl
3)
δ: 1.21 (t, 6H ,-CH
3); 3.49 (m, 4H ,-C
h 2cH
3); 7.19 (d,
j=5.60 Hz, 1H, 4-H); 7.49 (m, 1H, 7-H); 7.59 (m, 1H, 6-H); 7.73 (
j=8.00 Hz, 1H, 5-H); 8.15 (t, 2H, 3,8-H);
13c NMR (100 MHz, CDCl
3)
δ: 13.1 (
ch
3); 46.1 (-
ch
2-); 114.9 (C-4); 122.9 (C-6); 125.6 (C-8); 125.9 (C-7); 126.9 (C-5); 129.4 (C-6); 138.3 (C-10); 140.5 (C-3); 161.2 (C-1).
Embodiment 5:R
1=H, R
2=CH (CH
3)
2, R
3=C
2h
5time, the preparation of 1-(N-ethyl-N-iospropyl) amido isoquinoline 99.9
Oxidation quinoline 0.145 g (1 mmol) is added in 50 mL round-bottomed flasks, N-ethyl-diisopropylamine 0.52 mL (3 mmol), diphenylphosphite 0.404 g (2 mmol) and tetracol phenixin 0.5 mL, tetrahydrofuran (THF) 15 mL, stirred at ambient temperature, react 7 hours, along with the growth in reaction times, there is a large amount of white solids to generate, cross and filter precipitation, concentrated, column chromatography (V
etOAc: V
pE=1:6, v:v) be separated, obtain pale yellow oil.
Productive rate 65.0%;
1h NMR (400 MHz, CDCl
3)
δ: 1.18 (t, 3H ,-CH
2c
h 3); 1.40 (d, d,
j=7.20 Hz, 6H, CH (C
h 3) 2), 4.50 (m, 1H, C
h(CH
3) 2), 4.85 (m, 2H ,-C
h 2 cH
3) 6.74 (d,
j=9.60 Hz, 1H, 3-H); 7.16 (t, 1H, 6-H); 7.57-7.49 (m, 3H, 5,7,8-H); 7.82 (d,
j=9.20 Hz, 1H, 4-H);
13c NMR (100 MHz, CDCl
3)
δ: 13.4 (CH
2 ch
3); 21.2 (
ch (CH
3) 2), 44.9 (-
ch
2cH
3), 52.2 (
ch (CH
3) 2); 109.2 (C-3); 121.2 (C-6); 122.3 (C-10); 126.3 (C-5); 127.1 (C-8); 129.2 (C-7); 136.8 (C-4); 148.4 (C-9); 156.3 (C-2).
Claims (6)
1. the preparation method such as formula amido quinoline (I) and (II) Suo Shi, it is characterized in that, synthesize as follows: first substd quinolines (or substituted isoquinoline) and hydrogen peroxide are obtained by reacting to replace and are oxidized quinoline (or replacing isoquinoline); Then with tertiary amine (or secondary amine) under phosphorous acid ester and tetracol phenixin effect, at room temperature react; After reaction terminates, through extraction, dry, pressure reducing and steaming solvent, obtains general formula (I) and (II) amido quinoline crude product;
Wherein R
1represent the monosubstituted of one of following group: hydrogen base, nitro, amino, kharophen, cyano group, C1-3 alkyl, C1-3 alkoxyl group, halogen; R
2represent the monosubstituted of one of following group: C1-4 alkyl; R
3represent the monosubstituted of one of following group: C1-4 alkyl; R
2and R
3can be identical, also can not be identical.
2. the preparation method of amido quinoline as claimed in claim 1, is characterized in that, R
1preferably-H ,-NO
2,-Br ,-CH
3,-OCH
3; R
2, R
3preferably identical group-CH
3,-C
2h
5,-CH
2cH
2cH
3,-CH
2cH
2cH
2cH
3.
3. the preparation method of amido quinoline as claimed in claim 1, it is characterized in that, described phosphorous acid ester is dimethoxy phosphorous acid ester, diethoxy phosphorous acid ester, two positive propoxy phosphorous acid esters, diisopropoxy phosphorous acid ester, two phenoxy group phosphorous acid esters and benzyloxy phosphorous acid ester.
4. the preparation method of amido quinoline as claimed in claim 1, is characterized in that, described reaction solvent is one or more in THF, acetonitrile, toluene, dioxane, DMSO and ethanol, and preferred THF is solvent.
5. the preparation method of amido quinoline as claimed in claim 1, it is characterized in that, described reaction raw materials replaces oxidation quinoline (replacement isoquinoline): tertiary amine (secondary amine): phosphorous acid ester: the ratio of tetracol phenixin is 1 (mmol): 3 (mmol): 2 (mmol): 0.5 (mL).
6. the preparation method of amido quinoline as claimed in claim 1, it is characterized in that, temperature of reaction is 0-60 DEG C, preferred room temperature 20 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749013A (en) * | 2016-12-01 | 2017-05-31 | 安阳师范学院 | 2 dimethylamino N aoxidize the preparation method of quinoline |
| CN108752379A (en) * | 2018-07-04 | 2018-11-06 | 温州大学 | A kind of preparation method of isoquinolin phosphite ester compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862152A (en) * | 1971-07-31 | 1975-01-21 | Takeda Chemical Industries Ltd | 3-carbamoylamino-4-phenyl quinoline compounds |
| CN1914195A (en) * | 2004-02-04 | 2007-02-14 | 辉瑞产品公司 | Substituted quinoline compounds |
| CN103189377A (en) * | 2010-10-29 | 2013-07-03 | 辉瑞大药厂 | N1/n2-lactam acetyl-coa carboxylase inhibitors |
-
2014
- 2014-02-14 CN CN201410050717.7A patent/CN104844509A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862152A (en) * | 1971-07-31 | 1975-01-21 | Takeda Chemical Industries Ltd | 3-carbamoylamino-4-phenyl quinoline compounds |
| CN1914195A (en) * | 2004-02-04 | 2007-02-14 | 辉瑞产品公司 | Substituted quinoline compounds |
| CN103189377A (en) * | 2010-10-29 | 2013-07-03 | 辉瑞大药厂 | N1/n2-lactam acetyl-coa carboxylase inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| 柯典典: "2-胺基喹啉及2-喹啉膦酸酯类衍生物的合成研究", 《郑州大学硕士学位论文》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749013A (en) * | 2016-12-01 | 2017-05-31 | 安阳师范学院 | 2 dimethylamino N aoxidize the preparation method of quinoline |
| CN106749013B (en) * | 2016-12-01 | 2018-07-06 | 安阳师范学院 | 2- dimethylamino-N- aoxidizes the preparation method of quinoline |
| CN108752379A (en) * | 2018-07-04 | 2018-11-06 | 温州大学 | A kind of preparation method of isoquinolin phosphite ester compound |
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