CN102276526B - Synthesis method of 2-amino pyridine compounds - Google Patents

Synthesis method of 2-amino pyridine compounds Download PDF

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CN102276526B
CN102276526B CN 201110224788 CN201110224788A CN102276526B CN 102276526 B CN102276526 B CN 102276526B CN 201110224788 CN201110224788 CN 201110224788 CN 201110224788 A CN201110224788 A CN 201110224788A CN 102276526 B CN102276526 B CN 102276526B
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phenyl
cyano group
methoxy
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pentadiene nitrile
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CN102276526A (en
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董德文
信晓庆
梁永久
张睿
向德轩
刘绪
王自坤
杨继明
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Changchun Institute of Applied Chemistry of CAS
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Abstract

The invention provides a synthesis method of 2-amino pyridine compounds, belonging to the technical field of organic synthesis. The existing synthesis method has the disadvantages of difficult acquisition of raw materials, high catalyst cost, complicated reaction steps, harsh reaction conditions, serious environmental pollution, low yield, few substituent groups, specific substituent positions and atomic diseconomy. The synthesis method provided by the invention is characterized by comprising the following steps of: adding a 2,4-pentadiene nitrile compound and an amine compound in a molar ratio of 1.0:(1.0-2.5) to a solvent to form a reaction mixture; adding a base the amount of which is 0-250mol% of a substrate while stirring the reaction mixture; and then stirring at the temperature from room temperature to 150 DEG C for 3-24 hours to obtain a product namely the 2-amino pyridine compound. The synthesis method provided by the invention lowers the catalyst cost, relieves the pollution, simplifies the synthesis processes, has the advantages of mild reaction conditions, easy acquisition of raw materials, light side reaction, many substituent groups and wide application range, and has the yield of 58-81% depending on different reactions.

Description

A kind of PA compounds synthetic method
Technical field
The present invention relates to a kind of PA compounds synthetic method, as five carbon synthons, become the tactful one-step synthesis PA compounds of ring with ammoniac compounds through [5C+1N] with 2,4-pentadiene nitrile compounds, belong to technical field of organic synthesis.
Background technology
The PA compounds is important organic and medicine intermediate, can be used in synthetic multiple fine chemistry industry and pharmaceutical prod.For example, the amino 6-picoline of 2-can be used to make dyestuff and photographic developer; 2-amino-4-quinolyl base-Isosorbide-5-Nitrae-dihydropyridine compounds is a kind of medicine of Cardiovarscular; 2-amino-5-bromopyridine is for the synthesis of phosphatidylinositols PI3 kinase inhibitor, aminopyrazole derivatives selective dopamine D 3 receptor stimulant, and synthetic imidazo [1,2-a] medicine such as pyridine compounds VEGFR-2 inhibitor, can also be used for treating the various diseases such as autoimmune disease, inflammatory disease, cardiovascular and cerebrovascular diseases, nerve degenerative diseases, allergy; PA-3-methyl alcohol is the intermediate of synthetic Antidepressant-Mirtazapine, in addition, nitrogen protoxide (NO) synthetase inhibitors take PA-3-methyl alcohol and derivative thereof as effective constituent can suppress the synthetic too much immunologic injury of mediation of NO, at treatment septic shock, chronic rheumatoid arthritis, the disease aspects such as diabetes play a significant role.
The method of existing synthetic PA compounds mainly contains following two classes:
One, modifies pyridine ring
Following four kinds of schemes are specifically arranged:
1) pyridine and sodium amide carry out aminating reaction synthetic (US4386209);
2) by haloperidid palladium carbon (Org.Lett.2001,3,2729-2732.) or mantoquita (Tetrahedron Lett.2001,42, synthetic by ammonolysis reaction under katalysis 3251-3254.) etc.;
3) pyridine is through hydrogen peroxide oxidation, again by the nitrated one-tenth nitro of nitrosonitric acid pyridine oxide, carry out again reduction reaction obtain aminopyridine (Synth.Commun.2002,32,1681-1683.);
4) take cyanopyridine as raw material through catalytic hydrolysis, Hofmann degradation obtain aminopyridine (applied chemistry, 2004,21,530-531.).
Yet the such scheme raw material is not easy to obtain, the catalyzer cost is high, reactions steps is numerous and diverse, severe reaction conditions, contaminate environment serious, yield is not high.
Two, direct construction is with pyridine compounds and their and the derivative thereof of amino replacement
For example, by the PA compounds of the synthetic one type of replacement of the dithio keteal that contains cyano group (J.Org.Chem.2008,73,2442-2445).
The method has reduced the catalyzer cost, has alleviated pollution, and reaction conditions is gentle, has improved yield, still, have still that raw material is not easy to obtain, the numerous and diverse problem of reactions steps, and substituting group is few, the position of substitution is specific, the atom diseconomy.
Summary of the invention
The object of the invention is to, in the preparation of PA compounds, reducing catalyzer cost, pollution abatement, in the time of reaction conditions gentleness, raising yield, so that select the raw material that is easy to get, simplification to synthesize link, alleviate side reaction, we have invented a kind of PA compounds synthetic method.
The present invention is characterized in that, in solvent, add 2 of 1.0: 1.0～2.5 molar ratios, 4-pentadiene nitrile compounds and ammoniac compounds, form reaction mixture, the alkali that in the process of stirred reaction mixture, adds 0～250% mole of multiple of substrate, stirred 3～24 hours under ℃ temperature of room temperature～150 afterwards, obtain product PA compounds, reaction formula is as follows:
Figure BDA0000081646600000021
Positively effect of the present invention is, in the present invention's synthetic method, adopt 2,4-pentadiene nitrile compounds is as five carbon synthons, make up pyridine ring with ammoniac compounds through [5C+1N] step, synthesize and comprise that part replaces or entirely be substituted in the PA compounds of interior various replacements.The method adopts alkali as catalyzer, reduces catalyzer cost, pollution abatement; Reaction conditions is gentle, finishes synthetic in lesser temps, short period; Improve yield, productive rate is looked differential responses between 58～81%; Raw material is easy to get, and reactant is 2,4-pentadiene nitrile compounds and ammoniac compounds; Synthetic link is simplified, and namely finishes synthetic through a step; Light side-reaction, substituting group is many, the scope of application is wide, and its general formula of synthetic product PA compounds is:
Figure BDA0000081646600000022
Wherein, R 1Be cyano group, ester group; R 2Be connected with fluorine, chlorine, bromine, iodine, amino, hydroxyl, alkoxyl group, nitro for hydrogen, phenyl and at phenyl ring; R 3Be hydrogen, alkyl; R 4Be connected with fluorine, chlorine, bromine, iodine, amino, hydroxyl, alkoxyl group, nitro for phenyl and at phenyl ring.
Embodiment
In solvent, add 2 of 1.0: 1.0～2.5 molar ratios, 4-pentadiene nitrile compounds and ammoniac compounds, form reaction mixture, the alkali that in the process of stirred reaction mixture, adds 0～250% mole of multiple of substrate, under ℃ temperature of room temperature～150, stirred 3～24 hours, obtain product PA compounds, reaction formula is as follows:
Figure BDA0000081646600000031
Described solvent is the mixed solvent that organic solvent or organic solvent mix with water.Organic solvent comprises the alcohols of C1-C6 alkyl, is one of methyl alcohol, ethanol, propyl carbinol, ethylene glycol; Amides is one of dimethyl formamide, N,N-DIMETHYLACETAMIDE; And methyl-sulphoxide, methylene dichloride.In the alcohols of C1-C6 alkyl, amides, methyl-sulphoxide, methylene dichloride, select one.
Described 2,4-pentadiene nitrile compounds is one of following:
2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-5-(4-chloro-phenyl-)-2,4-pentadiene nitrile,
2-cyano group-3-(3-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(2-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-acetoxyl group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(4-chloro-phenyl-)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-4-methyl-5-phenyl-2,4-pentadiene nitrile.
Described ammoniac compounds is azanol or oxammonium hydrochloride.
Described alkali is mineral alkali or organic bases.Wherein mineral alkali is one of sodium hydroxide, potassium hydroxide, salt of wormwood; Organic bases is one of triethylamine, 1.8-diazabicylo (5.4.0) hendecene-7, triethylene diamine.
Embodiment 1:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-6-(4-p-methoxy-phenyl) pyridine 0.280 gram, productive rate 62.2%.Reaction formula is as follows:
Figure BDA0000081646600000032
The data characterization of product:
Mp：191～192℃；
1H?NMR(400MHz，CDCl 3，25℃)δ＝3.87(3H)，5.19(2H)，6.98(2H)，.10(1H)，7.70，(1H)，?7.94(2H)；
13C?NMR(125MHz，CDCl 3，25℃)δ＝55.4，88.4，109.5，114.2，117.2，128.8，130.3，141.7，159.0，160.0，161.5。
Illustrate that product is 2-Amino 3 cyano-6-(4-p-methoxy-phenyl) pyridine.
Embodiment 2:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-5-(4-chloro-phenyl-)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-6-(4-chloro-phenyl-) pyridine 0.290 gram, productive rate 63.1%.Reaction formula is as follows:
Figure BDA0000081646600000041
Embodiment 3:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(3-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Get white solid product 2-Amino 3 cyano-4-(3-p-methoxy-phenyl) pyridine 0.301 gram, productive rate 66.8%.Reaction formula is as follows:
Embodiment 4:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(2-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-4-(2-p-methoxy-phenyl) pyridine 0.295 gram, productive rate 65.6%.Reaction formula is as follows:
Figure BDA0000081646600000043
Embodiment 5:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-acetoxyl group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-acetoxyl group-6-(4-p-methoxy-phenyl) pyridine 0.355 gram, productive rate 65.3%.Reaction formula is as follows:
Figure BDA0000081646600000051
Embodiment 6:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-chloro-phenyl-)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-4-(4-chloro-phenyl-)-6-phenylpyridine 0.467 gram, productive rate 76.3%.Reaction formula is as follows:
Figure BDA0000081646600000052
Embodiment 7:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-phenyl-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-4-phenyl-6-phenylpyridine 0.405 gram, productive rate 74.7%.Reaction formula is as follows:
Figure BDA0000081646600000053
Embodiment 8:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; Under stirring at room, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.487 gram, productive rate 80.9%.Reaction formula is as follows:
Embodiment 9:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.5 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.488 gram, productive rate 81.0%.Reaction formula is as follows:
Figure BDA0000081646600000062
Embodiment 10:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-phenyl-4-methyl-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-4-phenyl-5-methyl-6-phenylpyridine 0.418 gram, productive rate 73.4%.Reaction formula is as follows:
Figure BDA0000081646600000063
Embodiment 11:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile, 0.13 milliliter of 50% aqueous hydroxylamine, 10 milliliters of dimethyl formamides; At room temperature stir, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-Amino 3 cyano-6-(4-p-methoxy-phenyl) pyridine 0.295 gram, productive rate 65.5%.Reaction formula is as follows:
Figure BDA0000081646600000064
Embodiment 12:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylene diamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.482 gram, productive rate 80.1%.Reaction formula is as follows:
Figure BDA0000081646600000071
Embodiment 13:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmoles 1, then 8-diazabicylo (5.4.0) hendecene-7 stirs 5h with reaction system under 80 ℃ of temperature, and reaction finishes; Through column chromatography, get faint yellow solid product 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.474 gram, productive rate 78.7%.Reaction formula is as follows:
Figure BDA0000081646600000072
Embodiment 14:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of methyl-sulphoxides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.468 gram, productive rate 77.7%.Reaction formula is as follows:
Figure BDA0000081646600000073
Embodiment: 15:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of ethanol; At room temperature stir, add simultaneously 4.4 mmole triethylamines, reflux 12h, stopped heating, reaction finishes; Through column chromatography, get faint yellow solid product 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.453 gram, productive rate 75.2%.Reaction formula is as follows:
Figure DEST_PATH_GDA0000249970751
。
Embodiment 16:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add simultaneously 4.4 mmole triethylamines, and then heat 3h under 120 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-Amino 3 cyano-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.479 gram, productive rate 79.6%.Reaction formula is as follows:
。

Claims (5)

1. PA compounds synthetic method, it is characterized in that, in solvent, add 2 of 1.0:1.0 ~ 2.5 molar ratios, 4-pentadiene nitrile compounds and ammoniac compounds, form reaction mixture, in the process of stirred reaction mixture, add the alkali of 0 ~ 250 % mole multiple of substrate, under ℃ temperature of room temperature ~ 150, stirred 3 ~ 24 hours afterwards, obtain product PA compounds, reaction formula is as follows:
Figure FDA0000270658091
，
Wherein, R 1Be cyano group, ester group; R 2Be connected with fluorine, chlorine, bromine, iodine, amino, hydroxyl, alkoxyl group, nitro for hydrogen, phenyl and at phenyl ring; R 3Be hydrogen, alkyl; R 4Be connected with fluorine, chlorine, bromine, iodine, amino, hydroxyl, alkoxyl group, nitro for phenyl and at phenyl ring;
Described ammoniac compounds is azanol or oxammonium hydrochloride.
2. synthetic method according to claim 1 is characterized in that, selects one as described solvent in the alcohols of C1-C6 alkyl, amides, methyl-sulphoxide, methylene dichloride.
3. synthetic method according to claim 2 is characterized in that, the alcohols of described C1-C6 alkyl is one of methyl alcohol, ethanol, propyl carbinol, ethylene glycol.
4. synthetic method according to claim 2 is characterized in that, described amides is one of dimethyl formamide, N,N-DIMETHYLACETAMIDE.
5. synthetic method according to claim 1 is characterized in that, and is described 2, and 4-pentadiene nitrile compounds is one of following:
2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-5-(4-chloro-phenyl-)-2,4-pentadiene nitrile,
2-cyano group-3-(3-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(2-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-acetoxyl group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(4-chloro-phenyl-)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-4-methyl-5-phenyl-2,4-pentadiene nitrile.
CN 201110224788 2011-08-08 2011-08-08 Synthesis method of 2-amino pyridine compounds Expired - Fee Related CN102276526B (en)

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WO2013144191A1 (en) * 2012-03-29 2013-10-03 Bayer Intellectual Property Gmbh Substituted 2-amino-3-cyanopyridines as inhibitors of sodium-calcium exchange and use thereof for cardiovascular diseases
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US4386209A (en) * 1982-04-08 1983-05-31 Reilly Tar & Chemical Corporation Chichibabin reaction

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