CN108558753A - The method that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl - Google Patents

The method that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl Download PDF

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CN108558753A
CN108558753A CN201810497453.8A CN201810497453A CN108558753A CN 108558753 A CN108558753 A CN 108558753A CN 201810497453 A CN201810497453 A CN 201810497453A CN 108558753 A CN108558753 A CN 108558753A
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source
releases
iron pentacarbonyl
carbostyril compound
aminated compounds
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高子伟
马富余
徐珊
张伟强
孙华明
张国防
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Shaanxi Normal University
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Shaanxi Normal University
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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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Abstract

The invention discloses a kind of methods preparing carbostyril compound as CO source of releases using iron pentacarbonyl, this method is using iron pentacarbonyl as CO source of releases, using palladium as catalyst, potassium phosphate and piperazine be alkali, acetonitrile is solvent, make 2 iodobenzene aminated compounds that coupling reaction occur under mild conditions with Terminal Acetylenes, generates carbostyril compound.The present invention is easy to operate, and reaction condition is mild, and catalyst amount is few, and CO source of release dosages are low, and toxicity is smaller, and cost is relatively low, and substrate applicability is wide, and target compound high income can be widely used for the preparation of natural products carbostyril compound.

Description

The method that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl
Technical field
The invention belongs to the synthesis technical fields of carbostyril compound, and in particular to one kind is with Fe (CO)5As an oxygen Change carbon (CO) source of release, 2- iodobenzenes aminated compounds is as reaction substrate, under conditions of need not add any ligand, with vinegar Sour palladium is that catalyst, potassium phosphate and piperazine are alkali, the method for synthesizing carbostyril compound in a mild condition.
Background technology
Carbostyril compound is a kind of critically important heterocyclic compound, has extensive bioactivity and medicinal valence Value, such as：Anti-malarial, antiviral, anti-inflammatory, anticancer etc., mother nucleus structure are considered as a kind of core in pharmaceutical synthesis research Structure is of great significance in organic synthesis.Therefore it is attracted wide public concern in organic synthesis field and pharmaceutical field.
There are many ways to synthesizing this compound, palladium chtalyst carbonylation method is the method for convenient and efficient.Usual earlier Using CO gases as carbonyl source, diethylamine is alkali, and 2- iodobenzenes aminated compounds is catalyzed in the presence of palladium and ligand and Terminal Acetylenes comes Carbostyril compound is prepared, reaction usually requires high-temperature and high-pressure conditions, and cost is higher, and the reaction time is longer.Therefore one is found Kind mild condition, safe and efficient synthetic method are necessary.
Invention content
Technical problem to be solved by the present invention lies in overcome existing carbostyril compound preparation method there are the shortcomings that, A kind of sources change CO are provided, ligand, reaction condition are mild, the reaction time is short, reaction product is single, safety is high without adding Effect, the preparation method of the high carbostyril compound of yield.
Technical solution is used by solving above-mentioned technical problem：Using acetonitrile as solvent, by 2- iodobenzenes aminated compounds with Under palladium and alkali effect, 20~60 DEG C are reacted 8~10 hours, and carbostyril compound is obtained for Terminal Acetylenes, iron pentacarbonyl.
Above-mentioned 2- iodobenzene phenolic compounds areR in formula1、R2、R3、R4It is separate represent H, F, CH3In any one, preferably R1、R4Represent H, R2、R3It is separate to represent CH3Or F.
Above-mentioned Terminal Acetylenes isR ' represents phenyl, C in formula1~C5Alkyl-substituted phenyl, C1~C2Alkoxy takes For phenyl, C5~C8Any one in alkyl, 2- thienyls, halogenophenyl, preferably R ' represent phenyl, p-methoxyphenyl, to first Base phenyl, to ethylphenyl, to any one in amyl phenyl, amyl, 3- aminomethyl phenyls, 2- thienyls, fluorophenyl.
Above-mentioned alkali is the mixture of any one and piperazine in potassium phosphate, triethylamine, potassium carbonate.
In above-mentioned preparation method, preferably the molar ratio of 2- iodobenzenes aminated compounds and Terminal Acetylenes is 1:1.2~2.0, pentacarbonyl The addition of iron is the 20%~60% of 2- iodobenzene aminated compounds moles, and the addition of palladium is 2- iodobenzene amine chemical combination The addition of the 1%~10% of object mole, potassium phosphate or triethylamine or potassium carbonate is 2- iodobenzene aminated compounds moles 2.0~4.0 times, the addition of piperazine is 1.0~2.0 times of 2- iodobenzene aminated compounds moles.
The present invention is using iron pentacarbonyl as CO source of releases, under the conditions of it is alkali that palladium, which is catalyst, potassium phosphate and piperazine, 2- iodobenzenes aminated compounds is set to undergo coupling reaction to produce carbostyril compound with Terminal Acetylenes.Relative to directly using CO gases as carbonyl Base supply source, the present invention is easy to operate, toxicity is smaller using iron pentacarbonyl as CO source of releases, easily controllable, overcomes CO gas The disadvantage that body toxicity is bigger, storage is inconvenient, reaction needs certain pressure relatively high to equipment requirement.In addition, the present invention without Ligand need to be added, used catalyst stablizes air and water, and reaction condition is mild, the reaction time is short, Atom economy is high, rear place Reason is simple and target product yield is high, is suitble to industrialized production.
Specific implementation mode
With reference to embodiment, the present invention is described in more detail, but invention which is intended to be protected is not limited only to this A little embodiments.
Embodiment 1
The following 2- phenylchinoline -1H-4- ketone of preparation structure formula
By 0.1095g (0.5mmol) 2- Iodoanilines, 66 μ L (0.60mmol) phenylacetylenes, 0.0056g (0.025 mmol) vinegar Sour palladium, potassium phosphate 0.3184g (1.5mmol), 0.0431g (0.5mmol) piperazines and 34 μ L (0.25mmol) iron pentacarbonyls, 3mL Shrek pipe is added in anhydrous acetonitrile, is stirred to react at 50 DEG C 10 hours, stops reaction, is down to room temperature naturally, pillar layer separation, Solid 2- phenylchinoline -1H-4- ketone, yield 86% are obtained, structural characterization data are：1H NMR(600MHz,DMSO)δ 11.72 (s, 1H), 8.11 (dd, J=8.0,0.9Hz, 1H), 7.87-7.82 (m, 2H), 7.78 (d, J=8.3Hz, 1H), 7.71-7.65 (m, 1H), 7.60 (dd, J=4.9,1.5Hz, 3H), 7.35 (t, J=7.4Hz, 1H), 6.34 (s, 1H)；13C NMR(151MHz,DMSO)δ 176.93,150.14,140.61,134.25,131.76,130.39,128.96,127.38, 124.78,124.67,123.29, 118.85,107.25.
Embodiment 2
The following 2- of preparation structure formula (4- methoxyphenyls) quinoline -1H-4- ketone
In embodiment 1, phenylacetylene used is replaced with equimolar 4- Methoxy-phenylacetylenes, other steps and embodiment 1 It is identical, solid 2- (4- methoxyphenyls) quinoline -1H-4- ketone, yield 81% are obtained, structural characterization data are：1H NMR (600MHz, DMSO) δ 11.59 (s, 1H), 8.09 (d, J=7.9Hz, 1H), 7.79 (dd, J=25.1,8.3Hz, 3H), 7.65 (t, J=7.5Hz, 1H), 7.32 (t, J=7.4Hz, 1H), 7.13 (d, J=8.6Hz, 2H), 6.31 (s, 1H), 3.85 (s, 3H)；13C NMR(151MHz,DMSO)δ176.83,161.03,149.68,140.51, 131.59,128.80,126.26, 124.77,124.64,123.06,118.60,114.37,106.47,55.42.
Embodiment 3
The following 2- of preparation structure formula (4- aminomethyl phenyls) quinoline -1H-4- ketone
In embodiment 1, phenylacetylene used is replaced with equimolar 4- methyl phenylacetylenes, other steps and 1 phase of embodiment Together, solid 2- (4- aminomethyl phenyls) quinoline -1H-4- ketone, yield 84% are obtained, structural characterization data are：1H NMR (600MHz, DMSO) δ 11.65 (s, 1H), 8.10 (d, J=7.5Hz, 1H), 7.81-7.61 (m, 4H), 7.44-7.27 (m, 3H),6.32(s,1H),2.40(s,3H)；13C NMR(151MHz,DMSO)δ176.90, 149.88,140.50,140.31, 131.69,131.28,129.51,127.20,124.85,124.68,123.13,118.64, 106.91,20.86.
Embodiment 4
The following 2- of preparation structure formula (4- ethylphenyls) quinoline -1H-4- ketone
In embodiment 1, phenylacetylene used is replaced with equimolar 4- Liquid Crystal Compounds Intermediate p-Ethyl-phenylacetylenes, other steps and 1 phase of embodiment Together, solid 2- (4- ethylphenyls) quinoline -1H-4- ketone, yield 80% are obtained, structural characterization data are：1H NMR (400MHz,CDCl3) δ 8.23 (d, J=8.0Hz, 1H), 7.85 (d, J=8.1Hz, 2H), 7.69 (t, J=7.7Hz, 1H), 7.56 (d, J=8.4Hz, 1H), 7.41 (t, J=7.5Hz, 1H), 7.35 (d, J=8.0Hz, 2H), 6.81 (s, 1H), 2.73 (q, J=7.6Hz, 2H), 1.28 (t, J=7.6Hz, 4H)；13C NMR(101MHz, CDCl3)δ178.61,163.80, 156.41,148.62,133.78,129.33,128.72,126.50,125.83,125.26, 124.15,118.19, 107.17,28.97,15.37.
Embodiment 5
The following 2- of preparation structure formula (4- amyls phenyl) quinoline -1H-4- ketone
In embodiment 1, phenylacetylene used is replaced with equimolar 4- amyl phenylacetylenes, other steps and 1 phase of embodiment Together, solid 2- (4- amyls phenyl) quinoline -1H-4- ketone, yield 85% are obtained, structural characterization data are：1H NMR (600MHz, DMSO) δ 11.65 (s, 1H), 8.10 (d, J=7.8Hz, 1H), 7.71 (dt, J=14.7,9.1 Hz, 4H), 7.48-7.26 (m, 3H), 6.33 (s, 1H), 2.66 (t, J=7.3Hz, 2H), 1.69-1.54 (m, 2H), 1.32 (dd, J= 11.7,5.2Hz, 4H), 0.87 (t, J=6.6Hz, 3H)；13C NMR(151MHz,DMSO)δ 176.90,150.03,145.11, 142.04,140.53,131.68,128.88,127.27,124.83,124.68,123.15, 118.67,106.94,34.80, 30.79,30.40,21.90,13.88.
Embodiment 6
The following 2- of preparation structure formula (2- thienyls) quinoline -1H-4- ketone
In embodiment 1, phenylacetylene used is replaced with equimolar 2- thiophene acetylenes, other steps and 1 phase of embodiment Together, solid 2- (2- thienyls) quinoline -1H-4- ketone, yield 84% are obtained, structural characterization data are：1H NMR (600MHz, DMSO) δ 11.65 (s, 1H), 8.10 (d, J=7.0Hz, 1H), 8.01-7.59 (m, 4H), 7.33 (d, J= 36.4Hz,2H),6.35(s,1H)；13C NMR(151MHz,DMSO)δ176.78,143.51,140.38, 136.17, 131.90,129.56,128.52,128.17,124.63,123.41,118.58,106.14.
Embodiment 7
The following 2- amyloquinoline -1H-4- ketone of preparation structure formula
In embodiment 1, phenylacetylene used is replaced with equimolar 1- heptyne, other steps are same as Example 1, obtain Solid 2- amyloquinoline -1H-4- ketone, yield 45%, structural characterization data are：1H NMR(600MHz, DMSO)δ11.48 (s, 1H), 8.04 (d, J=7.9Hz, 1H), 7.61 (t, J=7.1Hz, 1H), 7.53 (d, J=8.2 Hz, 1H), 7.27 (t, J =7.4Hz, 1H), 5.92 (s, 1H), 2.58 (t, J=7.7Hz, 2H), 1.72-1.62 (m, 2H), 1.32 (d, J=3.3Hz, 5H), 0.88 (t, J=6.8Hz, 4H)；13C NMR(101MHz,DMSO)δ177.58, 154.01,140.63,131.88, 125.23,125.13,123.17,118.33,108.10,33.68,31.17,28.48,22.29, 14.31.
Embodiment 8
The following 6- methyl -2- phenylchinoline -1H-4- ketone of preparation structure formula
In embodiment 1,2- Iodoanilines used are replaced with equimolar 4- methyl -2- Iodoanilines, other steps and implementation Example 1 is identical, obtains solid 6- methyl -2- phenylchinoline -1H-4- ketone, yield 82%, and structural characterization data are：1H NMR (600MHz, DMSO) δ 11.58 (s, 1H), 7.99 (d, J=8.0Hz, 1H), 7.82 (d, J=3.2Hz, 2H), 7.56 (d, J= 25.3Hz, 4H), 7.17 (d, J=7.9Hz, 1H), 6.29 (s, 1H), 2.44 (s, 3H)；13C NMR(151MHz,DMSO)δ 176.82,149.75,141.83,140.68,134.28,130.33,128.95, 127.34,124.90,124.71, 122.91,117.96,107.23,21.37.
Embodiment 9
Following 6- methyl -2- (4- methoxyphenyls) quinoline -1H-4- ketone of preparation structure formula
In embodiment 1,2- Iodoanilines used are replaced with equimolar 4- methyl -2- Iodoanilines, phenylacetylene equimolar 4- Methoxy-phenylacetylenes are replaced, other steps are same as Example 1, obtain 6- methyl -2- (4- methoxyphenyls) quinoline -1H- 4- ketone, yield 90%, structural characterization data are：1H NMR (600MHz, DMSO) δ 11.48 (s, 1H), 7.97 (d, J= 8.0Hz, 1H), 7.78 (d, J=8.0Hz, 2H), 7.53 (s, 1H), 7.13 (t, J=8.8Hz, 3H), 6.25 (s, 1H), 3.84 (s,3H),2.43(s,3H)；13C NMR(151MHz,DMSO)δ176.78, 160.99,149.46,141.71,140.64, 128.76,126.25,124.77,124.66,122.77,117.88,114.38, 106.37,55.45,21.38.
Embodiment 10
Following 6- methyl -2- (3- aminomethyl phenyls) quinoline -1H-4- ketone of preparation structure formula
In embodiment 1,2- Iodoanilines used are replaced with equimolar 4- methyl -2- Iodoanilines, phenylacetylene equimolar 3- methyl phenylacetylenes are replaced, other steps are same as Example 1, obtain solid 6- methyl -2- (3- aminomethyl phenyls) quinoline -1H- 4- ketone, yield 91%, structural characterization data are：1H NMR (600MHz, DMSO) δ 11.56 (s, 1H), 8.00 (d, J= 7.8Hz, 1H), 7.60 (dd, J=29.9,23.4Hz, 3H), 7.48-7.33 (m, 2H), 7.16 (d, J=7.5Hz, 1H), 6.28 (s, 1H), 2.43 (d, J=10.0Hz, 6H)；13C NMR(151MHz,DMSO) δ176.80,149.85,141.78, 140.67,138.31,134.24,130.94,128.86,127.79,124.86,124.70, 124.46,122.91, 117.94,107.15,21.38,20.96.
Embodiment 11
Fluorophenyl quinoline -1H-4- ketone between the following 6- methyl -2- of preparation structure formula
In embodiment 1,2- Iodoanilines used are replaced with equimolar 4- methyl -2- Iodoanilines, phenylacetylene equimolar 3- fluorobenzene acetylene is replaced, other steps are same as Example 1, obtain fluorophenyl quinoline -1H-4- ketone between solid 6- methyl -2-, Its yield is 70%, and structural characterization data are：1H NMR (600MHz, DMSO) δ 11.61 (s, 1H), 8.00 (d, J=7.9Hz, 1H), 7.80-7.57 (m, 3H), 7.53 (s, 1H), 7.43 (s, 1H), 7.18 (d, J=7.6Hz, 1H), 6.35 (s, 1H), 2.45(s,3H)；13C NMR(151MHz,DMSO)δ176.87,163.00,161.38,148.26, 142.04,140.61, 136.48,131.10 (d, J=8.3Hz), 124.89 (d, J=58.2Hz), 123.58,122.92,117.99,117.14 (d, ), J=20.8Hz 114.33 (d, J=23.4Hz), 107.54,21.37.
Embodiment 12
The fluoro- 2- phenylchinolines -1H-4- ketone of the following 7- of preparation structure formula
In embodiment 1,2- Iodoanilines used are replaced with the fluoro- 2- Iodoanilines of equimolar 5-, other steps and embodiment 1 is identical, obtains the fluoro- 2- phenylchinolines -1H-4- ketone of solid 7-, yield 75%, and structural characterization data are：1H NMR (600MHz, DMSO) δ 11.76 (s, 1H), 8.16 (dd, J=8.7,6.6Hz, 1H), 7.84 (s, 2H), 7.66-7.44 (m, 4H), 7.21 (t, J=7.8Hz, 1H), 6.36 (s, 1H)；13C NMR(151MHz,DMSO)δ 176.25,164.44,162.89, (150.47,133.96,130.54,129.02,127.99 d, J=5.3Hz), 127.29,121.83,111.98 (d, J= 16.9Hz), 107.50,103.78 (d, J=15.6Hz).

Claims (9)

1. a kind of method preparing carbostyril compound as CO source of releases using iron pentacarbonyl, it is characterised in that：With acetonitrile For solvent, by 2- iodobenzenes aminated compounds and Terminal Acetylenes, iron pentacarbonyl under palladium and alkali effect, 20~60 DEG C of reactions 8~10 Hour, obtain carbostyril compound；
Above-mentioned alkali is the mixture of any one and piperazine in potassium phosphate, triethylamine, potassium carbonate.
2. the method according to claim 1 that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl, It is characterized in that：The 2- iodobenzene aminated compounds isR in formula1、R2、R3、R4It is separate represent H, F、CH3In any one.
3. the method according to claim 2 that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl, It is characterized in that：The R1、R4Represent H, R2、R3It is separate to represent CH3Or F.
4. the method according to claim 1 that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl, It is characterized in that：The Terminal Acetylenes isR ' represents phenyl, C in formula1~C5Alkyl-substituted phenyl, C1~C2Alkoxy Substituted-phenyl, C5~C8Any one in alkyl, 2- thienyls, halogenophenyl.
5. the method according to claim 4 that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl, It is characterized in that：The R ' represent phenyl, p-methylphenyl, to butyl phenyl, to amyl phenyl, to ethylphenyl, to methoxyl group Any one in phenyl, amyl, 2- thienyls, fluorophenyl.
6. preparing quinolones chemical combination as CO source of releases using iron pentacarbonyl according to Claims 1 to 5 any one The method of object, it is characterised in that：The molar ratio of the 2- iodobenzenes aminated compounds and Terminal Acetylenes is 1:1.2~2.0.
7. preparing quinolones chemical combination as CO source of releases using iron pentacarbonyl according to Claims 1 to 5 any one The method of object, it is characterised in that：The addition of the iron pentacarbonyl is the 20%~60% of 2- iodobenzene aminated compounds moles.
8. preparing quinolones chemical combination as CO source of releases using iron pentacarbonyl according to Claims 1 to 5 any one The method of object, it is characterised in that：The addition of the palladium is the 1%~10% of 2- iodobenzene aminated compounds moles.
9. preparing quinolones chemical combination as CO source of releases using iron pentacarbonyl according to Claims 1 to 5 any one The method of object, it is characterised in that：The addition of the piperazine is 1.0~2.0 times of 2- iodobenzene aminated compounds moles, described The addition of potassium phosphate or triethylamine or potassium carbonate is 2.0~4.0 times of 2- iodobenzene aminated compounds moles.
CN201810497453.8A 2018-05-22 2018-05-22 The method that carbostyril compound is prepared as CO source of releases using iron pentacarbonyl Pending CN108558753A (en)

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CN110204489A (en) * 2019-07-09 2019-09-06 陕西师范大学 Use the safe synthetic method of the carbostyril compound in solid carbonyl source
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Application publication date: 20180921