CN105085272A - Synthesis method for aryl or heteroaryl ester compound - Google Patents
Synthesis method for aryl or heteroaryl ester compound Download PDFInfo
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- CN105085272A CN105085272A CN201510543566.3A CN201510543566A CN105085272A CN 105085272 A CN105085272 A CN 105085272A CN 201510543566 A CN201510543566 A CN 201510543566A CN 105085272 A CN105085272 A CN 105085272A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/40—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of primary alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Abstract
The invention relates to a synthesis method for an aryl or heteroaryl ester compound shown in the formula (III). The method includes the following steps: under the atmosphere of oxygen and the existence of catalyst, nitrogen-containing bidentate ligand, accelerant and auxiliary, in organic solvent, compound in the formula (I) reacts with compound in the formula (II), so that the compound in the formula (III) is obtained, wherein R is chosen from phenyl, furyl, phenyl with a substituent group or furyl with the substituent group, and the substituent group is a C1-C6 alkyl group, a C1-C6 alkoxy group or halogen. By means of the catalyst, the ligand, the accelerant and the auxiliary and the total choice and synergy of organic solvent, the synthesis method can obtain the target product at high yield, moreover, the reaction conditions are mild, and thereby the application prospect is good.
Description
Technical field
The present invention relates to a kind of method by ester compound, especially relate to the synthetic method of a kind of aryl or heteroaryl ester compound, belong to medicine intermediate synthesis field.
Background technology
Ester class formation is one of very important class functional group in organic chemistry, and it all has corresponding chapters and sections to write among teaching material in organic chemistry, pharmaceutical chemistry, synthetic chemistry.Tradition prior art often adopts carboxylic acid, aldehyde, alcohol to change into corresponding ester class, and along with the development of organic catalysis chemistry, the method relating to catalyzed conversion receives the concern of people more.
Through years of researches and development, had the multiple method preparing ester compound about catalysis to be seen in report in prior art, and received the concern of people and deeply probe into, exemplarily property is as follows:
AkiIzumi etc. (" Oxidativedimerizationofprimaryalcoholstoesterscatalyzedb yiridiumcomplexes ", TetrahedronLetters, 2006,47,9199-9201) report a kind of employing complex of iridium catalysis oxidation of primary alcohols dimerization, and then form the method for ester compound, its reaction formula is as follows:
BrooksE.Maki etc. (" N-Heterocycliccarbene-catalyzedoxidations ", Tetrahedron, 2009,65, method that 3102-3109) report the catalysis of a kind of N-heterocycle carbine, that vinyl carbinol and benzylalcohol are oxidized to ester compound, and achieve good yield, its reaction formula is as follows:
In addition, ZhangJing etc. (" FacileConversionofAlcoholsintoEstersandDihydrogenCatalyz edbyNewRutheniumComplexes ", J.Am.Chem.Soc., 2005,127,10840-10841) there was reported a kind of method adopting ruthenium complexe alcohols to be converted into ester class.
As mentioned above, although disclose the synthetic method of multiple ester compound in prior art, these methods can not meet the widespread demand of synthesis far away, especially for the further expansion of the substrate scope of application, very necessary especially.
Therefore, still there is the necessity continuing research in the synthetic method for new ester compound, this is of great immediate significance in organic synthesis especially medicine intermediate synthesis technical field.
Summary of the invention
In order to seek the novel method for synthesizing of ester compound, present inventor has performed deep research and exploration, after having paid enough creative works, thus completing the present invention.
Specifically, technical scheme of the present invention and content relate to the synthetic method of ester compound shown in a kind of following formula (III), described method comprises: under oxygen atmosphere, in organic solvent, under catalyzer, nitrogenous bitooth ligand, promotor and auxiliary agent exist, following formula (I) compound and following formula (II) compound react, thus obtain described formula (III) compound
Wherein, R is selected from phenyl, furyl, with substituent phenyl or with substituent furyl, described substituting group is C
1-C
6alkyl, C
1-C
6alkoxy or halogen.
In described synthetic method of the present invention, described C
1-C
6the implication of alkyl refers to the straight or branched alkyl with 1-6 carbon atom, such as can be methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl or n-hexyl etc. in non-limiting manner.
In described synthetic method of the present invention, described C
1-C
6the implication of alkoxyl group refers to the C of above-mentioned implication
1-C
6the group obtained after alkyl is connected with Sauerstoffatom.
In described synthetic method of the present invention, the implication of described halogen refers to haloid element, non-exclusively such as can be F, Cl, Br or I.
In described synthetic method of the present invention, described catalyzer is Rh (COD)
2bF
4(two (1,5-cyclooctadiene) Tetrafluoroboric acid rhodium), Rh (COD)
2sO
3cF
3(two (1,5-cyclooctadiene) trifluoromethanesulfonic acid rhodium) or Rh (NBD)
2bF
4any one in (two (norbornadiene) Tetrafluoroboric acid rhodium), most preferably is Rh (COD)
2sO
3cF
3.
In described synthetic method of the present invention, described nitrogenous bitooth ligand is any one in following formula L1-L3,
Most preferably be L1.
In described synthetic method of the present invention, described promotor is the two benzsulfamide (NFSI) of N-fluoro.
In described synthetic method of the present invention, described auxiliary agent is any one in two (trifluoromethane sulphonyl) inferior amine salt of 1-cyanogen propyl group-3-methylimidazolium nitrate, 1-cyanogen propyl group-3-methyl imidazolium tetrafluoroborate or 1-cyanogen propyl group-3-Methylimidazole, most preferably is two (trifluoromethane sulphonyl) inferior amine salt of 1-cyanogen propyl group-3-Methylimidazole.
In described synthetic method of the present invention, described organic solvent is benzene, toluene, chlorobenzene, p-Xylol, DMF (N, dinethylformamide), any one in DMSO (dimethyl sulfoxide (DMSO)) or acetonitrile, be preferably DMF, DMSO or acetonitrile, most preferably be acetonitrile.
Wherein, the consumption of this organic solvent is not particularly limited, and those skilled in the art can carry out suitable selection and determine, such as, carry out and aftertreatment and carry out suitable selection according to convenient reaction.
In described synthetic method of the present invention, the mol ratio of described formula (I) compound and formula (II) compound is 1:1.4-2, such as, can be 1:1.4,1:1.6,1:1.8 or 1:2.
In described synthetic method of the present invention, the mol ratio of described formula (II) compound and catalyzer is 1:0.05-0.08, such as, can be 1:0.05,1:0.06,1:0.07 or 1:0.08.
In described synthetic method of the present invention, the mol ratio of described formula (II) compound and nitrogenous bitooth ligand is 1:0.1-0.15, such as, can be 1:0.1,1:0.12,1:0.14 or 1:0.15.
In described synthetic method of the present invention, the mol ratio of described formula (II) compound and promotor is 1:0.1-0.2, such as, can be 1:0.1,1:0.15 or 1:0.2.
In described synthetic method of the present invention, the mol ratio of described formula (II) compound and auxiliary agent is 1:0.15-0.2, such as, can be 1:0.15,1:0.17,1:0.19 or 1:0.2.
In described synthetic method of the present invention, temperature of reaction is 50-70 DEG C, such as, can be 50 DEG C, 60 DEG C or 70 DEG C.
In described synthetic method of the present invention, the reaction times is 4-8 hour, such as, can be 4 hours, 6 hours or 8 hours.
In described synthetic method of the present invention, aftertreatment after reaction terminates is conventional aftertreatment, such as can be specific as follows: after reaction terminates, filter, by filtrate adjust ph to 6-7, then fully wash with saturated aqueous common salt, use acetone extract 2-3 time again, merge organic phase, and with anhydrous magnesium sulfate drying, then underpressure distillation, residue is crossed 300-400 order silica gel column chromatography and is separated, with volume ratio be the mixed solution of the chloroform of 1:2 and sherwood oil as elutriant, thus obtain described formula (III) compound.
In described synthetic method of the present invention, the reaction mass of employing all prepares by prior art and/or buys use.
In sum, the invention provides a kind of method of aryl or heteroaryl ester compound, described method is selected with collaborative by the summation of catalyzer, part, promotor and auxiliary agent and organic solvent, thus can by two kinds of alcohol direct reaction, and obtain object product with high yield, and reaction conditions is gentle, has a good application prospect.
Embodiment
Below by specific embodiment, the present invention is described in detail; but the purposes of these exemplary embodiments and object are only used for exemplifying the present invention; not any type of any restriction is formed to real protection scope of the present invention, more non-protection scope of the present invention is confined to this.
Embodiment 1
Under oxygen atmosphere, in appropriate organic solvent acetonitrile, add 100mmol above formula (I) compound, 140mmol above formula (II) compound, 5mmol catalyzer Rh (COD)
2sO
3cF
3, the two benzsulfamide (NFSI) of nitrogenous bitooth ligand L1,10mmol accelerant N-fluoro of 10mmol and 15mmol auxiliary agent 1-cyanogen propyl group-3-Methylimidazole pair (trifluoromethane sulphonyl) inferior amine salt; Then 50 DEG C are warming up to, and stirring reaction 8 hours at such a temperature.
After reaction terminates, filter, by filtrate adjust ph to 6-7, then fully wash with saturated aqueous common salt, use acetone extract 2-3 time again, merge organic phase, and with anhydrous magnesium sulfate drying, then underpressure distillation, residue is crossed 300-400 order silica gel column chromatography and is separated, with volume ratio be the mixed solution of the chloroform of 1:2 and sherwood oil as elutriant, thus obtain above formula (III) compound, productive rate is 96.8%.
1HNMR(CDCl
3,400MHz):δ8.08(m,2H),7.42(d,2H,J＝7.2Hz),7.28(m,3H),7.06(m,2H),6.72(d,1H,J＝16.0Hz),6.39(m,1H),4.95(d,2H,J＝6.4Hz)。
Embodiment 2
Under oxygen atmosphere, in appropriate organic solvent acetonitrile, add 100mmol above formula (I) compound, 170mmol above formula (II) compound, 7mmol catalyzer Rh (COD)
2sO
3cF
3, the two benzsulfamide (NFSI) of nitrogenous bitooth ligand L1,15mmol accelerant N-fluoro of 12mmol and 17mmol auxiliary agent 1-cyanogen propyl group-3-Methylimidazole pair (trifluoromethane sulphonyl) inferior amine salt; Then 60 DEG C are warming up to, and stirring reaction 6 hours at such a temperature.
After reaction terminates, filter, by filtrate adjust ph to 6-7, then fully wash with saturated aqueous common salt, use acetone extract 2-3 time again, merge organic phase, and with anhydrous magnesium sulfate drying, then underpressure distillation, residue is crossed 300-400 order silica gel column chromatography and is separated, with volume ratio be the mixed solution of the chloroform of 1:2 and sherwood oil as elutriant, thus obtain above formula (III) compound, productive rate is 96.6%.
1HNMR(CDCl
3,400MHz):δ8.05(d,2H,J＝8.8Hz),7.34(m,7H),6.77(d,1H,J＝16.0Hz),6.41(m,1H),4.97(d,2H,J＝6.8Hz)。
Embodiment 3
Under oxygen atmosphere, in appropriate organic solvent acetonitrile, add 100mmol above formula (I) compound, 200mmol above formula (II) compound, 8mmol catalyzer Rh (COD)
2sO
3cF
3, the two benzsulfamide (NFSI) of nitrogenous bitooth ligand L1,20mmol accelerant N-fluoro of 15mmol and 20mmol auxiliary agent 1-cyanogen propyl group-3-Methylimidazole pair (trifluoromethane sulphonyl) inferior amine salt; Then 70 DEG C are warming up to, and stirring reaction 4 hours at such a temperature.
After reaction terminates, filter, by filtrate adjust ph to 6-7, then fully wash with saturated aqueous common salt, use acetone extract 2-3 time again, merge organic phase, and with anhydrous magnesium sulfate drying, then underpressure distillation, residue is crossed 300-400 order silica gel column chromatography and is separated, with volume ratio be the chloroform of 1:2 and the mixed solution of sherwood oil as elutriant, thus obtain above formula (III) compound (wherein, t-Bu is the tertiary butyl), productive rate is 96.5%.
1HNMR(CDCl
3,400MHz):δ8.02(d,2H,J＝8.0Hz),7.46(m,4H),7.34(m,3H),6.72(d,1H,J＝16.0Hz),6.41(m,1H),4.97(d,2H,J＝7.2Hz),1.37(s,9H)。
Embodiment 4
Under oxygen atmosphere, in appropriate organic solvent acetonitrile, add 100mmol above formula (I) compound, 150mmol above formula (II) compound, 6mmol catalyzer Rh (COD)
2sO
3cF
3, the two benzsulfamide (NFSI) of nitrogenous bitooth ligand L1,18mmol accelerant N-fluoro of 12mmol and 16mmol auxiliary agent 1-cyanogen propyl group-3-Methylimidazole pair (trifluoromethane sulphonyl) inferior amine salt; Then 55 DEG C are warming up to, and stirring reaction 7 hours at such a temperature.
After reaction terminates, filter, by filtrate adjust ph to 6-7, then fully wash with saturated aqueous common salt, use acetone extract 2-3 time again, merge organic phase, and with anhydrous magnesium sulfate drying, then underpressure distillation, residue is crossed 300-400 order silica gel column chromatography and is separated, with volume ratio be the chloroform of 1:2 and the mixed solution of sherwood oil as elutriant, thus obtain above formula (III) compound (wherein, t-Bu is the tertiary butyl), productive rate is 95.8%.
1HNMR(CDCl
3,400MHz):δ7.59(m,1H),7.44(d,2H,J＝7.2Hz),7.27(m,4H),6.74(d,1H,J＝16.0Hz),6.51(m,1H),6.37(m,1H),4.99(d,2H,J＝6.4Hz)。
As above visible, when using reaction method of the present invention, object product can be obtained with high yield, thus having a good application prospect and production potential in organic synthesis field.
Embodiment 5-12
Embodiment 5-8: except catalyzer is replaced with Rh (COD)
2bF
4outward, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 5-8.
Embodiment 9-12: except catalyzer is replaced with Rh (NBD)
2bF
4outward, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 9-12.
The results are shown in following table 1.
Table 1
From upper table 1 data, Rh (COD)
2sO
3cF
3there is best catalytic effect, even if with its very similar Rh (COD)
2bF
4, its catalytic effect also has obvious reduction, and Rh (NBD)
2bF
4then reduce more obvious.
Embodiment 13-24
Embodiment 13-16: except replacing with except L2 by nitrogenous bitooth ligand, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 13-16.
Embodiment 17-20: except replacing with except L3 by nitrogenous bitooth ligand, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 17-20.
Embodiment 21-24: except being omitted by nitrogenous bitooth ligand, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 21-24.
The results are shown in following table 2.
Table 2
As can be seen here, in nitrogenous bitooth ligand L1-L3, L1 effect is best, and the effect of L2-L3 with do not use effect during part to be more or less the same.
Embodiment 25-28
Embodiment 25-28: except promotor is omitted, other operation is all constant, thus is repeated embodiment 1-4, obtain embodiment 25-28, find that its products collection efficiency is reduced to 90.2-91.4%, thus demonstrate this material and can play facilitation effect, improve products collection efficiency.
Embodiment 29-40
Embodiment 29-32: except auxiliary agent being replaced with 1-cyanogen propyl group-3-methylimidazolium nitrate, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 29-32.
Embodiment 33-36: except auxiliary agent being replaced with 1-cyanogen propyl group-3-methyl imidazolium tetrafluoroborate, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 33-36.
Embodiment 37-40: except being omitted by auxiliary agent, other operation is all constant, thus is repeated embodiment 1-4, obtains embodiment 37-40.
The results are shown in following table 3.
Table 3
As can be seen here, the existence of auxiliary agent can improve products collection efficiency to a certain extent, but two (trifluoromethane sulphonyl) inferior amine salt of 1-cyanogen propyl group-3-Methylimidazole has the most significantly positive effect, and other the two kinds degree improved not are very large.
Embodiment 41-46
Except using following organic solvent, other operation is all constant, thus repeats to implement embodiment 1-4, obtains embodiment 41-46.The organic solvent used, corresponding embodiment and products collection efficiency see the following form 4.
Table 4
As can be seen here, acetonitrile has best solvent effect, and the effect of other organic solvent all will lower than acetonitrile, but DMF and DMSO all can obtain the good yield higher than 90%.
In sum, the invention provides a kind of method of aryl or heteroaryl ester compound, described method is selected with collaborative by the summation of catalyzer, part, promotor and auxiliary agent and organic solvent, thus high yield can obtain object product, and reaction conditions is gentle, has a good application prospect.
Should be appreciated that the purposes of these embodiments is only not intended to for illustration of the present invention limit the scope of the invention.In addition; also should understand; after having read technology contents of the present invention, those skilled in the art can make various change, amendment and/or modification to the present invention, and these all equivalent form of values fall within the protection domain that the application's appended claims limits equally.
Claims (10)
1. the synthetic method of ester compound shown in a following formula (III), described method comprises: under oxygen atmosphere, in organic solvent, under catalyzer, nitrogenous bitooth ligand, promotor and auxiliary agent exist, following formula (I) compound and following formula (II) compound react, thus obtain described formula (III) compound
Wherein, R is selected from phenyl, furyl, with substituent phenyl or with substituent furyl, described substituting group is C
1-C
6alkyl, C
1-C
6alkoxy or halogen.
2. synthetic method as claimed in claim 1 or 2, is characterized in that: described catalyzer is Rh (COD)
2bF
4(two (1,5-cyclooctadiene) Tetrafluoroboric acid rhodium), Rh (COD)
2sO
3cF
3(two (1,5-cyclooctadiene) trifluoromethanesulfonic acid rhodium) or Rh (NBD)
2bF
4any one in (two (norbornadiene) Tetrafluoroboric acid rhodium), most preferably is Rh (COD)
2sO
3cF
3.
3. synthetic method as claimed in claim 2, is characterized in that: described nitrogenous bitooth ligand is any one in following formula L1-L3,
Most preferably be L1.
4. the synthetic method as described in any one of claim 1-3, is characterized in that: described promotor is the two benzsulfamide (NFSI) of N-fluoro.
5. the synthetic method as described in any one of claim 1-4, it is characterized in that: described auxiliary agent is any one in two (trifluoromethane sulphonyl) inferior amine salt of 1-cyanogen propyl group-3-methylimidazolium nitrate, 1-cyanogen propyl group-3-methyl imidazolium tetrafluoroborate or 1-cyanogen propyl group-3-Methylimidazole, most preferably is two (trifluoromethane sulphonyl) inferior amine salt of 1-cyanogen propyl group-3-Methylimidazole.
6. the synthetic method as described in any one of claim 1-5, is characterized in that: the mol ratio of described formula (I) compound and formula (II) compound is 1:1.4-2.
7. the synthetic method as described in any one of claim 1-6, is characterized in that: the mol ratio of described formula (II) compound and catalyzer is 1:0.05-0.08.
8. the synthetic method as described in any one of claim 1-7, is characterized in that: the mol ratio of described formula (II) compound and nitrogenous bitooth ligand is 1:0.1-0.15.
9. the synthetic method as described in any one of claim 1-8, is characterized in that: the mol ratio of described formula (II) compound and promotor is 1:0.1-0.2.
10. the synthetic method as described in any one of claim 1-9, is characterized in that: the mol ratio of described formula (II) compound and auxiliary agent is 1:0.15-0.2.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530381A (en) * | 2018-05-07 | 2018-09-14 | 上海科技大学 | A method of preparing diamine derivative by carboxylic acid amide esters |
| CN108707096A (en) * | 2018-05-07 | 2018-10-26 | 上海科技大学 | A method of preparing aminoalcohol derivative |
| CN108947798A (en) * | 2018-05-30 | 2018-12-07 | 上海科技大学 | A kind of method of degradation polymer |
-
2015
- 2015-08-28 CN CN201510543566.3A patent/CN105085272A/en active Pending
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530381A (en) * | 2018-05-07 | 2018-09-14 | 上海科技大学 | A method of preparing diamine derivative by carboxylic acid amide esters |
| CN108707096A (en) * | 2018-05-07 | 2018-10-26 | 上海科技大学 | A method of preparing aminoalcohol derivative |
| CN108707096B (en) * | 2018-05-07 | 2021-03-19 | 上海科技大学 | Process for preparing aminoalcohol derivatives |
| CN108530381B (en) * | 2018-05-07 | 2021-09-21 | 上海科技大学 | Method for preparing diamine derivative from amide ester |
| CN108947798A (en) * | 2018-05-30 | 2018-12-07 | 上海科技大学 | A kind of method of degradation polymer |
| CN108947798B (en) * | 2018-05-30 | 2021-03-02 | 上海科技大学 | Method for degrading polymer |
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