CN104987327A - Catalyzed synthesis method of tetrazole derivative - Google Patents
Catalyzed synthesis method of tetrazole derivative Download PDFInfo
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- CN104987327A CN104987327A CN201510409730.1A CN201510409730A CN104987327A CN 104987327 A CN104987327 A CN 104987327A CN 201510409730 A CN201510409730 A CN 201510409730A CN 104987327 A CN104987327 A CN 104987327A
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- 0 *c(cc1)ccc1N(C(CC1)=O)C1=O Chemical compound *c(cc1)ccc1N(C(CC1)=O)C1=O 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Abstract
The invention relates to a catalyzed synthesis method of tetrazole derivative, (see specification). The method comprises the following steps: in an organic solvent, in the existence of a first catalyst, alkali, accessory ingredients and additives, stirring a compound in formula (I) and a compound in formula (II) to react for 2 to 4 hours under 50 to 80 DEG C, then adding a compound of formula (III) and a second catalyst into a reaction system, continuously stirring to react for 4 to 7 hours to obtain a compound of formula (IV), (see specification), wherein R is C1-C6 alkyl, C1-C6 alkoxy, halogen or nitro. By virtue of two-section reaction and by adopting different catalysts, under the comprehensive synergistic effect of the alkali, accessory ingredients and additives, the tetrazole derivative can be obtained at high yield, a brand new synthesis method is provided for the synthesis of the compound, and the application prospect and potential in the industry are good.
Description
Technical field
The present invention relates to a kind of synthetic method of nitrogen heterocyclic ring compounds, relate more particularly to a kind of process for catalytic synthesis of tetrazole derivatives, belong to organic intermediate synthesis field.
Background technology
In organic chemistry especially medicinal chemistry art, the structural unit simultaneously containing nitrogen and oxygen is prevalent among medical compounds, bioactive natural products and material compound as a kind of important construction module.Such as, zalcitabine is a kind of potential AntiHIV1 RT activity reagent, indole alkaloid Fendleridine is well-known antitumor and anticancer agent, 9-(tetrahydrofuran base) VITAMIN B4 is a kind of important ACI etc., all containing hemiacetal ethers structure (simultaneously containing nitrogen and oxygen) in these compounds.
In addition, the significant element that ethers structure or medical compounds are modified, it can improve the lipotropy of medical compounds.
Therefore, the novel method for synthesizing developing this compounds will produce great and active influence to bioactive molecules field.
In general, the method for synthesizing this compounds such as hemiacetal ether has the hydroamination reaction of the unsaturated link(age) of metal catalytic, also has multiple report in addition, such as:
Cheng Xiaohui etc. (" Palladium-Catalyzed addition of R2NH todouble bonds.Synthesis of α-amino tetrahydrofuran and pyran rings ", Tetrahedron, 2001,57,5445-5450) report a kind of R of palladium chtalyst
1r
2nH and the addition reaction containing double bond ether, its reaction formula is as follows:
(" the Metal-free a-CH amination of ethers withhypervalent sulfonylimino-γ such as Masahito Ochiai
3-bromane that acts as an active nitrenoid ", Chem.Commun., 2012,48,5280-5282) disclose a kind of without the need to selectivity C-H amination reaction that is transition metal-catalyzed, ether, its reaction formula is as follows:
As mentioned above, the synthetic method that some contain the structural unit compound of nitrogen and oxygen simultaneously has been disclosed in prior art, but, although these all can realize reaction or the preparation of some ether compounds, it still also exists, and the specific substrates scope of application is wide in range not, materials conversion rate has much room for improvement, processing condition need the problems such as milder.
The present inventor through studying intensively with great concentration and aiming to provide a kind of process for catalytic synthesis of tetrazole derivatives for many years, thus has expanded the synthetic method of this compounds, possesses wide actual application value and market outlook.
Summary of the invention
In order to overcome above-mentioned pointed many defects, 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 process for catalytic synthesis of tetrazole derivatives shown in a kind of following formula (IV),
Described method comprises: in organic solvent, under the first catalyzer, alkali, auxiliary agent and additive exist, following formula (I) compound and following formula (II) compound stirring reaction 2-4 hour at 50-80 DEG C, then in reaction system, following formula (III) compound and the second catalyzer is added, continue insulated and stirred reaction 4-7 hour, thus obtain described formula (IV) compound
Wherein, R is C
1-C
6alkyl, C
1-C
6alkoxyl group, halogen or nitro.
In described process for catalytic synthesis of the present invention, unless otherwise prescribed, from start to finish, 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 process for catalytic synthesis of the present invention, unless otherwise prescribed, from start to finish, C
1-C
6the implication of alkoxyl group refers to C defined above
1-C
6the group obtained after alkyl is connected with Sauerstoffatom.
In described process for catalytic synthesis of the present invention, unless otherwise prescribed, from start to finish, the implication of halogen refers to haloid element, non-exclusively such as can be F, Cl, Br or I.
In described process for catalytic synthesis of the present invention, described first catalyzer is Palladous nitrate, palladous sulfate, bipyridyl palladium (Pd (py)
2), acid chloride (Pd (OAc)
2), palladium trifluoroacetate (Pd (TFA)
2), palladium acetylacetonate (Pd (acac)
2), tetrakis triphenylphosphine palladium (Pd (PPh
3)
4), tetramino Palladous chloride (Pd (NH
3)
4cl
2), 1,5-cyclooctadiene Palladous chloride (PdCl
2(cod) any one), most preferably is PdCl
2(cod).
In described process for catalytic synthesis of the present invention, described alkali is Na
2cO
3, NaOH, KOH, K
3pO
4, N, N-diisopropylethylamine (DIPEA), Dimethylamino pyridine (DMPA), 1, any one in 4-diazabicylo [2.2.2] octane (DABCO), sodium ethylate, potassium tert.-butoxide, diisopropylamine, diisopropyl ethanolamine etc., most preferably is DMPA.
In described process for catalytic synthesis of the present invention, described auxiliary agent is SmI
2(means of samarium iodide).
In described process for catalytic synthesis of the present invention, described additive is any one in 1-n-hexyl-3-Methylimidazole hexafluorophosphate, 1-n-hexyl-3-Methylimidazole fluoroform sulphonate, 1-n-hexyl-3-methyl imidazolium tetrafluoroborate, most preferably is 1-n-hexyl-3-Methylimidazole fluoroform sulphonate.
In described process for catalytic synthesis of the present invention, described second catalyzer is following formula ruthenium compound:
In described process for catalytic synthesis of the present invention, described organic solvent is benzene, toluene, santochlor, tetracol phenixin, acetonitrile, DMA (N, N-N,N-DIMETHYLACETAMIDE), DMF (N, dinethylformamide), DMSO (dimethyl sulfoxide (DMSO)), ethanol, NMP (N-Methyl pyrrolidone), 1, any one in 4-dioxane etc., most preferably be Isosorbide-5-Nitrae-dioxane.
The restriction that the consumption of described organic solvent is strict, those skilled in the art can carry out suitable selection to its consumption, such as, can carry out according to making aftertreatment be easy to, reacting the amount of carrying out smoothly and carry out suitable selection.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and formula (II) compound is 1:1.5-2.5, such as, can be 1:1.5,1:2 or 1:2.5.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and formula (III) compound is 1:1.2-2, such as, can be 1:1.2,1:1.5,1:1.8 or 1:2.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and the first catalyzer is 1:0.03-0.07, such as, can be 1:0.03,1:0.05 or 1:0.07.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and alkali is 1:1-2, such as, can be 1:1,1:1.5 or 1:2.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and auxiliary agent is 1:0.1-0.25, such as, can be 1:0.1,1:0.15,1:0.2 or 1:0.25.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and additive is 1:0.1-0.2, such as, can be 1:0.1,1:0.15 or 1:0.2.
In described process for catalytic synthesis of the present invention, the mol ratio of described formula (I) compound and the second catalyzer is 1:0.02-0.04, such as, can be 1:0.02,1:0.04 or 1:0.05.
In described process for catalytic synthesis of the present invention, aftertreatment after reaction terminates is as follows: after reaction terminates, naturally cool to room temperature, filter, filtrate is fully washed 2-3 time with saturated sodium bicarbonate aqueous solution, isolates organic phase, anhydrous magnesium sulfate drying, concentrating under reduced pressure, gained residue crosses the 200-300 object silica gel column chromatography petrol ether/ethyl acetate mixed solvent of 1:2 (be with volume ratio be elutriant), thus obtains described formula (IV) compound.
As mentioned above, present inventors have proposed a kind of new catalytic synthetic method of tetrazole derivatives, the method is reacted by two-part and is adopted different catalyzer, and the comprehensive synergy of combined alkali, auxiliary agent and additive, thus high yield can obtain tetrazole derivatives, synthesis for this compounds provides brand-new synthetic method, industrially has a good application prospect and potentiality.
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.
Wherein, unless otherwise defined, namely the second used in all of the embodiments illustrated catalyzer is the ruthenium compound (being collectively referred to as " above formula ruthenium compound ") of structure above.
Embodiment 1
Under room temperature, in the appropriate organic solvent Isosorbide-5-Nitrae-dioxane in reactor, add 100mmol above formula (I) compound, 150mmol above formula (II) compound, 3mmol first catalyst P dCl
2(cod), 100mmol alkali DMPA, 10mmol auxiliary agent SmI
2with 10mmol additive 1-n-hexyl-3-Methylimidazole fluoroform sulphonate, be warming up to 50 DEG C and stirring reaction 4 hours; Then, in reaction system, add 120mmol above formula (III) compound and 2mmol second catalyzer above formula ruthenium compound, continue insulated and stirred and react 4 hours;
After reaction terminates, naturally cool to room temperature, filter, filtrate is fully washed 2-3 time with saturated sodium bicarbonate aqueous solution, isolates organic phase, anhydrous magnesium sulfate drying, concentrating under reduced pressure, gained residue crosses the 200-300 object silica gel column chromatography petrol ether/ethyl acetate mixed solvent of 1:2 (be with volume ratio be elutriant), thus obtains above formula (IV) compound, and productive rate is 95.7%.
1H NMR(CDCl
3,400MHz):δ8.03-7.97(m,2H),7.36-7.25(m,2H),6.05(dd,J＝6.1,2.8Hz,1H),4.43(dd,J＝12.0,6.2Hz,1H),4.18-4.11(m,2H),3.97-3.85(m,3H),2.42(s,3H)。
HRMS(ESI)([M+Na]
+)：269.10。
Embodiment 2
Under room temperature, in the appropriate organic solvent Isosorbide-5-Nitrae-dioxane in reactor, add 100mmol above formula (I) compound, 200mmol above formula (II) compound, 5mmol first catalyst P dCl
2(cod), 150mmol alkali DMPA, 20mmol auxiliary agent SmI
2with 15mmol additive 1-n-hexyl-3-Methylimidazole fluoroform sulphonate, be warming up to 70 DEG C and stirring reaction 3 hours; Then, in reaction system, add 150mmol above formula (III) compound and 3mmol second catalyzer above formula ruthenium compound, continue insulated and stirred and react 5 hours;
After reaction terminates, naturally cool to room temperature, filter, filtrate is fully washed 2-3 time with saturated sodium bicarbonate aqueous solution, isolates organic phase, anhydrous magnesium sulfate drying, concentrating under reduced pressure, gained residue crosses the 200-300 object silica gel column chromatography petrol ether/ethyl acetate mixed solvent of 1:2 (be with volume ratio be elutriant), thus obtains above formula (IV) compound, and productive rate is 95.4%.
1H NMR(CDCl
3,400MHz):δ8.14(d,J＝8.6Hz,2H),7.44(d,J＝8.6Hz,2H),6.08(dd,J＝6.0,2.9Hz,1H),4.45(dd,J＝12.0,6.0Hz,1H),4.22-4.07(m,2H),3.99-3.85(m,3H)。
HRMS(ESI)([M+Na]
+)：289.05。
Embodiment 3
Under room temperature, in the appropriate organic solvent Isosorbide-5-Nitrae-dioxane in reactor, add 100mmol above formula (I) compound, 250mmol above formula (II) compound, 7mmol first catalyst P dCl
2(cod), 200mmol alkali DMPA, 25mmol auxiliary agent SmI
2with 20mmol additive 1-n-hexyl-3-Methylimidazole fluoroform sulphonate, be warming up to 80 DEG C and stirring reaction 2 hours; Then, in reaction system, add 200mmol above formula (III) compound and 4mmol second catalyzer above formula ruthenium compound, continue insulated and stirred and react 7 hours;
After reaction terminates, naturally cool to room temperature, filter, filtrate is fully washed 2-3 time with saturated sodium bicarbonate aqueous solution, isolates organic phase, anhydrous magnesium sulfate drying, concentrating under reduced pressure, gained residue crosses the 200-300 object silica gel column chromatography petrol ether/ethyl acetate mixed solvent of 1:2 (be with volume ratio be elutriant), thus obtains above formula (IV) compound, and productive rate is 95.1%.
1H NMR(CDCl
3,400MHz):δ8.14(d,J＝8.8Hz,2H),6.97(d,J＝8.8Hz,2H),6.08(dd,J＝6.2,2.8Hz,1H),4.42(dd,J＝12.0,6.3Hz,1H),4.19-4.05(m,2H),3.97-3.88(m,3H),3.84(s,3H)。
HRMS(ESI)([M+Na]
+)：285.09。
Embodiment 4
Under room temperature, in the appropriate organic solvent Isosorbide-5-Nitrae-dioxane in reactor, add 100mmol above formula (I) compound, 180mmol above formula (II) compound, 4mmol first catalyst P dCl
2(cod), 160mmol alkali DMPA, 15mmol auxiliary agent SmI
2with 17mmol additive 1-n-hexyl-3-Methylimidazole fluoroform sulphonate, be warming up to 60 DEG C and stirring reaction 3 hours; Then, in reaction system, add 140mmol above formula (III) compound and 3mmol second catalyzer above formula ruthenium compound, continue insulated and stirred and react 5 hours;
After reaction terminates, naturally cool to room temperature, filter, filtrate is fully washed 2-3 time with saturated sodium bicarbonate aqueous solution, isolates organic phase, anhydrous magnesium sulfate drying, concentrating under reduced pressure, gained residue crosses the 200-300 object silica gel column chromatography petrol ether/ethyl acetate mixed solvent of 1:2 (be with volume ratio be elutriant), thus obtains above formula (IV) compound, and productive rate is 95.2%.
1H NMR(CDCl
3,400MHz):δ9.03(s,1H),8.55(d,J＝7.7Hz,1H),8.32(d,J＝8.1Hz,1H),7.69(t,J＝8.0Hz,1H),6.15(dd,J＝5.3,2.7Hz,1H),4.48(dd,J＝12.1,5.6Hz,1H),4.23-4.12(m,2H),4.01-3.87(m,3H)。
HRMS(ESI)([M+Na]
+)：300.07。
The impact of the embodiment 5-12: the first catalyzer
PdCl is replaced except adopting the first different catalyzer
2(cod) outward, other operation is all constant, and implement embodiment 5-12 respectively in the mode identical with embodiment 1-4 respectively, the first catalyzer, corresponding relation and the result that use are as shown in table 1 below.
Table 1
As seen from the above table, the first catalyzer directly affects the net result of reaction in this reaction system, wherein PdCl
2(cod) there is best catalytic effect, and other palladium compound all causes final products collection efficiency to have remarkable reduction.
Embodiment 13-22: the impact of alkali
Except adopting different alkali and replacing DMPA, other operation is all constant, and implement embodiment 13-22 respectively in the mode identical with embodiment 1-4 respectively, the alkali used, corresponding relation and result are as shown in table 2 below.
Table 2
Can find out from the experimental result of table 2, the kind of alkali also remarkably influenced final result, and wherein DMPA has best effect, and other alkali all causes productive rate to have to a certain degree or even significantly reducing.
Embodiment 23-26: the impact of auxiliary agent
Respectively by the auxiliary agent SmI in embodiment 1-4
2omitted, other operation is all constant, thus implements embodiment 23-26 respectively in the mode identical with embodiment 1-4 respectively, the results are shown in following table 3:
Table 3
As can be seen here, the existence of auxiliary agent can improve productive rate significantly, and when there is not auxiliary agent, and products collection efficiency has and significantly reduces.
Embodiment 27-38: the impact of additive
Embodiment 27-30: except additive being replaced with 1-n-hexyl-3-Methylimidazole hexafluorophosphate, other operation is all constant, implements embodiment 27-30 respectively respectively in the mode identical with embodiment 1-4.
Embodiment 31-34: except additive being replaced with 1-n-hexyl-3-methyl imidazolium tetrafluoroborate, other operation is all constant, implements embodiment 31-34 respectively respectively in the mode identical with embodiment 1-4.
Embodiment 35-38: except being omitted by the additive in embodiment 1-4 respectively, other operation is all constant, thus implements embodiment 35-38 respectively in the mode identical with embodiment 1-4 respectively.
The results are shown in following table 4:
Table 4
As can be seen here, the difference of additive can affect final products collection efficiency significantly, and wherein, 1-n-hexyl-3-Methylimidazole fluoroform sulphonate has best collaborative promoter action, and other additive productive rate has significant reduction, but still the good yield higher than 85% can be obtained.
Also can find out, when not using additive, productive rate, lower than 80%, has the significantly reduction of highly significant.This proves the existence of additive, can play excellent collaborative promoter action together with other component.
Embodiment 39-48: the impact of organic solvent
Except adopting different organic solvents and replacing Isosorbide-5-Nitrae-dioxane, other operation is all constant, and implement embodiment 39-48 respectively in the mode identical with embodiment 1-4 respectively, the organic solvent used, corresponding relation and result are as shown in table 5 below.
Table 5
As can be seen here, solvent affects to some extent on net result equally, and wherein Isosorbide-5-Nitrae-dioxane has best solvent effect, and the effect of other solvent decreases, but still can obtain quite high products collection efficiency.
Comprehensively above-mentioned, the present invention creatively proposes a kind of synthetic method of tetrazole derivatives, the method is reacted by two-part and is adopted different catalyzer, and the comprehensive synergy of combined alkali, auxiliary agent and additive, thus high yield can obtain tetrazole derivatives, synthesis for this compounds provides brand-new synthetic method, industrially has a good application prospect and potentiality.
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. a process for catalytic synthesis for tetrazole derivatives shown in following formula (IV),
Described method comprises: in organic solvent, under the first catalyzer, alkali, auxiliary agent and additive exist, following formula (I) compound and following formula (II) compound stirring reaction 2-4 hour at 50-80 DEG C, then in reaction system, following formula (III) compound and the second catalyzer is added, continue stirring reaction 4-7 hour, thus obtain described formula (IV) compound
Wherein, R is C
1-C
6alkyl, C
1-C
6alkoxyl group, halogen or nitro.
2. process for catalytic synthesis as claimed in claim 1, is characterized in that: described first catalyzer is Palladous nitrate, palladous sulfate, bipyridyl palladium (Pd (py)
2), acid chloride (Pd (OAc)
2), palladium trifluoroacetate (Pd (TFA)
2), palladium acetylacetonate (Pd (acac)
2), tetrakis triphenylphosphine palladium (Pd (PPh
3)
4), tetramino Palladous chloride (Pd (NH
3)
4cl
2), 1,5-cyclooctadiene Palladous chloride (PdCl
2(cod) any one), most preferably is PdCl
2(cod).
3. process for catalytic synthesis as claimed in claim 1 or 2, is characterized in that: described alkali is Na
2cO
3, NaOH, KOH, K
3pO
4, N, N-diisopropylethylamine (DIPEA), Dimethylamino pyridine (DMPA), 1, any one in 4-diazabicylo [2.2.2] octane (DABCO), sodium ethylate, potassium tert.-butoxide, diisopropylamine, diisopropyl ethanolamine etc., most preferably is DMPA.
4. the process for catalytic synthesis as described in any one of claim 1-3, is characterized in that: described auxiliary agent is SmI
2.
5. the process for catalytic synthesis as described in any one of claim 1-4, it is characterized in that: described additive is any one in 1-n-hexyl-3-Methylimidazole hexafluorophosphate, 1-n-hexyl-3-methyl imidazolium tetrafluoroborate, most preferably is 1-n-hexyl-3-Methylimidazole fluoroform sulphonate.
6. the process for catalytic synthesis as described in any one of claim 1-5, it is characterized in that: described organic solvent is benzene, toluene, dichlorobenzene, tetracol phenixin, acetonitrile, DMA (N, N-N,N-DIMETHYLACETAMIDE), DMF (N, dinethylformamide), DMSO (dimethyl sulfoxide (DMSO)), ethanol, NMP (N-Methyl pyrrolidone), 1, any one in 4-dioxane etc., most preferably be Isosorbide-5-Nitrae-dioxane.
7. the process for catalytic synthesis as described in any one of claim 1-6, is characterized in that: the mol ratio of described formula (I) compound and formula (II) compound is 1:1.5-2.5.
8. the process for catalytic synthesis as described in any one of claim 1-7, is characterized in that: the mol ratio of described formula (I) compound and formula (III) compound is 1:1.2-2.
9. the process for catalytic synthesis as described in any one of claim 1-8, is characterized in that: the mol ratio of described formula (I) compound and the first catalyzer is 1:0.03-0.07.
10. the process for catalytic synthesis as described in any one of claim 1-9, is characterized in that: the mol ratio of described formula (I) compound and alkali is 1:1-2.
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