CN112745275B - Synthetic method of 1,3, 4-oxadiazole heterocyclic compound - Google Patents
Synthetic method of 1,3, 4-oxadiazole heterocyclic compound Download PDFInfo
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
Abstract
The invention belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of a 1,3, 4-oxadiazole heterocyclic compound. The invention takes benzaldehyde derivatives and diazo trivalent iodine reagent as raw materials, under the illumination, no catalyst is needed, methylene dichloride is taken as solvent, and the reaction is carried out at room temperature, so as to obtain the 1,3, 4-oxadiazole heterocyclic compound. By using the method provided by the invention, the 1,3, 4-oxadiazole heterocyclic derivative can be obtained by a one-step method at room temperature for 10-15 hours, and the yield is 48-89%. The reaction uses simple and easily obtained raw materials, and under the illumination condition, the 1,3, 4-oxadiazole heterocyclic derivative is simply, conveniently and rapidly synthesized in one step, so that a simple, high-efficiency and mild synthesis method is provided for synthesizing the 1,3, 4-oxadiazole heterocyclic derivative.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and drug synthesis, and particularly relates to a synthesis method of a 1,3, 4-oxadiazole heterocyclic compound.
Background
1,3, 4-oxadiazole heterocycles are widely present in drug molecules due to their good biological and pharmacological activities, and also can be used as intermediates in synthetic chemistry, and are widely used in organic synthesis, and are attracted to and studied by many scientists (a) Sharma, s.; sharma, p.k.; kumar, n.; dudhee, r.pharma.chemica, 2010,2,253, (b) Khalilullah, h.; ahsan, m.j.; hedaitullah, m.; khan, s.; ahmed, b.mini-rev.med.chem.,2012,12,789. The polycyclic compound with 1,3, 4-oxadiazole as a mother nucleus has good biological activity in the aspects of pain relieving, anticonvulsant efficacy, antifungal, insecticidal and the like, and a plurality of medicaments sold in the market, including an anti-AIDS medicament, namely Latiravir, an antihypertensive medicament, namely Nexadil and docetaxel with an anti-cancer effect, all contain the 1,3, 4-oxadiazole heterocyclic mother nucleus.
The current methods for the synthesis of 1,3, 4-oxadiazole heterocycles mainly involve the cyclisation of the hydrazide [ (a) Chu, w.j.; yang, y.; chen, c.f.org.lett.2010,12,3156; (b) dolman, S.J; gosselin F, O' shear, p.d.; davies, i.e.j.org.chem.2006; 71:9548.], C-H cross-oxidation of N-phenylhydrazide [ Zhang, L.; zhao, x.; sting, X.; zhang, x.; lu, S.; luo, l.; jia, x.tetrahedron lett.2016,57,5669] and acid catalyzed tandem cyclization of hydrazides and nitroalkanes (Aksenov, a.v.; Khamraev, v.; Aksenov, n.a.; Kirilov, n.k.; Domenyuk, d.a.; Zelensky, v.a.; Rubin, m.rsc Advances 2019,9, 6636). However, these methods have disadvantages in that a metal catalyst, an external oxidizing agent, and severe reaction conditions are required. Therefore, the development of a novel simple and efficient synthesis method of the 1,3, 4-oxadiazole heterocyclic derivative is of great significance.
Disclosure of Invention
The technical problem solved by the invention is as follows: in order to expand the universality of a substrate, the substrate which is simple and easy to obtain and an environment-friendly solvent are used, the reaction steps are simplified, and the method which is simple, takes benzaldehyde derivatives and trivalent iodine reagents as raw materials, can be used for one-step reaction, does not need to add any catalyst, and can be used for simply, conveniently and efficiently synthesizing the 1,3, 4-oxadiazole derivatives under the illumination condition is provided.
The invention provides a method for synthesizing 1,3, 4-oxadiazole, which comprises the steps of taking benzaldehyde derivatives and trivalent iodine reagents as raw materials, adding an organic solvent, and reacting under the illumination condition to generate the 1,3, 4-oxadiazole heterocyclic derivatives.
The reaction conditions are as follows: reacting at room temperature under the condition of illumination, wherein the reaction time is 10-15 hours.
The organic solvent is dichloromethane, trichloromethane, acetonitrile or methanol.
The molar ratio of the raw materials is 1:1.5 of benzaldehyde derivatives and trivalent iodine reagents.
The benzaldehyde as raw material may be benzaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde, 4-methylbenzaldehyde, 4-tert-butylbenzaldehyde, 4-methoxybenzaldehyde, 3-methylbenzaldehyde, 2-cyanobenzaldehyde, 2-methoxybenzaldehyde, 2, 4-dimethoxybenzaldehyde, 2, 3-dimethylbenzaldehyde, 3, 4-dimethylbenzaldehyde, 2, 4-dichlorobenzaldehyde, 2, 6-dichlorobenzaldehyde, 2,4, 6-trimethylbenzaldehyde.
The structural formula of the raw material trivalent iodine is shown as the following formula,
wherein R is 1 The radical being R 1 ＝COOEt，COOMe，COOCH 2 Ph can smoothly react to obtain the corresponding 1,3, 4-oxadiazole heterocyclic derivative.
The diazo trivalence iodine reagent is synthesized by the following steps:
1-methoxy-1, 2-benziodoyl 3(1H) one (4.0g,14.4mmol,1equiv), trimethylsilyl triflate (2.6mL,14.4mmol,1equiv) and dichloromethane (25mL) were added to a 100mL round bottom flask at room temperature. After stirring for 30 minutes at room temperature, ethyl diazoacetate (31.8mmol,2.2equiv) is slowly added, stirring is carried out for 3 hours, the filtrate is dried in a rotary manner after the reaction is finished, and the crude product is recrystallized by diethyl ether/dichloromethane (5:1) under a low-temperature pump to obtain pure diazo trivalent iodine reagent which is stored at low temperature.
Preparation of 1,3, 4-oxadiazole derivative: under the condition of illumination, adding a benzaldehyde derivative (1equiv), a diazo trivalent iodine reagent (1.5equiv) and an organic solvent into a 10mL reaction tube, stirring at room temperature for 10-15 hours, performing TLC (thin layer chromatography) plate tracking reaction, then spin-drying the filtrate, and further separating and purifying the crude product by silica gel column chromatography to obtain the 1,3, 4-oxadiazole.
The post-reaction treatment is simple and convenient, and pure substituted 1,3, 4-oxadiazole derivatives can be obtained by using a mixed solvent of petroleum ether and ethyl acetate as an eluent by a simple column chromatography separation method.
The invention has the advantages that: 1,3, 4-oxadiazole is an important biological and pharmaceutical active molecule, and has wide application in the fields of medicine and pharmacology. According to the invention, benzaldehyde and a diazo trivalent iodine reagent derivative are used as raw materials for the first time, no catalyst is required to be added under the illumination condition, different substituted 1,3, 4-oxadiazole heterocyclic parent nuclei are constructed at room temperature by a one-step method, and the yield reaches 48-89%.
Detailed Description
The synthetic method of the diazo trivalent iodine reagent comprises the following steps: 1-methoxy-1, 2-benziodoyl 3(1H) one (4.0g,14.4mmol,1equiv), trimethylsilyl triflate (2.6mL,14.4mmol,1equiv) and dichloromethane (25mL) were added to a 100mL round bottom flask at room temperature. After stirring for 30 minutes at room temperature, ethyl diazoacetate (31.8mmol,2.2equiv) is slowly added and stirred for 3 hours, after the reaction is finished, the filtrate is dried in a rotary manner, and the crude product is recrystallized by diethyl ether/dichloromethane (5:1) under a low-temperature pump to obtain a pure diazo trivalent iodine reagent which is stored at low temperature.
The invention relates to a synthesis reaction process of 1,3, 4-oxadiazole derivative and a structural formula of the obtained product
Example 1
Under the illumination condition, benzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 12 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the yield of the target compound 3a which is 85%. 1 H NMR(400MHz,CDCl 3 )δ8.10(d,J＝7.7Hz,2H),7.56-7.46(m,3H),4.48(q,J＝7.1Hz,2H),1.42(t,J＝7.1Hz,3H).
Example 2
Under the illumination condition, 4-fluorobenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 12 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound 3b with the yield of 81%. 1 H NMR(400MHz,CDCl 3 )δ8.14-8.09(m,2H),7.20-7.17(m,2H),4.50(q,J＝7.1Hz,2H),1.42(t,J＝7.1Hz,3H).
Example 3
Under the illumination condition, 4-chlorobenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, and the mixture reacts for 12 hours at room temperature and is separated by silica gel column chromatography, so that the yield of the target compound 3c is 84%. 1 H NMR(400MHz,CDCl 3 )δ8.04(d,J＝8.3Hz,2H),7.46(d,J＝8.3Hz,2H),4.49(q,J＝7.1Hz,2H),1.42(t,J＝7.1Hz,3H).
Example 4
Under the illumination condition, 4-methylbenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, reaction is carried out for 12 hours at room temperature, and silica gel column chromatography is carried out to separate out the yield of the target compound 3d to be 87%. 1 H NMR(300MHz,CDCl 3 )δ8.02(d,J＝8.6Hz,2H),6.95(d,J＝8.6Hz,2H),4.47(q,J＝7.1Hz,2H),3.82(s,3H),1.40(t,J＝7.1Hz,3H).
Example 5
Under the illumination condition, 4-methoxybenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 12 hours at room temperature, and silica gel column chromatography is carried out to separate the target compound 3e with the yield of 85%. 1 H NMR(300MHz,CDCl 3 )δ7.97(d,J＝8.7Hz,1H),6.60(dd,J＝8.7,2.3Hz,1H),6.56(d,J＝2.3Hz,1H),4.53(q,J＝7.2Hz,2H),3.97(s,3H),3.89(s,3H),1.47(t,J＝7.1Hz,3H).
Example 6
Under the illumination condition, 4-tert-butyl benzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 12 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound 3f with the yield of 89%. 1 H NMR(400MHz,CDCl 3 )δ8.09(d,J＝8.5Hz,2H),7.55(d,J＝8.5Hz,2H),4.55(q,J＝7.1Hz,2H),1.49(t,J＝7.1Hz,3H),1.36(s,9H).
Example 7
Under the illumination condition, 3-methoxybenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 12 hours at room temperature, and silica gel column chromatography is carried out to separate out 3g of the target compound with the yield of 79%. 1 H NMR(400MHz,CDCl 3 )δ7.73(d,J＝7.8Hz,1H),7.67(s,1H),7.44(t,J＝8.0Hz,1H),7.15(dd,J＝8.3,2.5Hz,1H),4.56(q,J＝7.1Hz,2H),3.89(s,3H),1.49(t,J＝7.1Hz,3H).
Example 8
Under the illumination condition, 2-cyanobenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound with the yield of 65 h.
Example 9
Under the illumination condition, 2-methoxybenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound 3i with the yield of 70%. 1 H NMR(400MHz,CDCl 3 )δ8.05-8.03(m,1H),7.60-7.55(m,1H),7.13-7.08(m,2H),4.56(q,J＝7.1Hz,2H),4.01(s,3H),1.49(t,J＝7.1Hz,3H).
Example 10
Under the illumination condition, 2, 4-dimethoxybenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography is carried out to separate the target compound 3j with the yield of 64%. 1 H NMR(500MHz,CDCl 3 )δ7.97(d,J＝8.8Hz,1H),6.60(dd,J＝8.8,2.3Hz,1H),6.55(d,J＝2.3Hz,1H),4.54(q,J＝7.1Hz,2H),3.97(s,3H),3.89(s,3H),1.47(t,J＝7.1Hz,3H).
Example 11
Under the illumination condition, 2, 6-dichlorobenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound 3k with the yield of 65%. 1 H NMR(400MHz,CDCl 3 )δ7.49(t,J＝4.1Hz,3H),4.58(q,J＝7.1Hz,2H),1.50(t,J＝7.1Hz,2H).
Example 12
Under the illumination condition, 2, 4-dichlorobenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound 3l with the yield of 56%. 1 H NMR(400MHz,CDCl 3 )δ8.04(d,J＝8.5Hz,1H),7.61(d,J＝1.9Hz,1H),7.44(dd,J＝8.5,1.5Hz,1H),4.56(q,J＝7.1Hz,2H),1.48(t,J＝7.1Hz,3H).
Example 13
Under the illumination condition, 2, 3-dimethylbenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, and the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the target compound with the yield of 3m being 57%. 1 H NMR(400MHz,CDCl 3 )δ7.80(d,J＝7.8Hz,1H),7.36(d,J＝7.4Hz,1H),7.24(d,J＝7.8Hz,1H),4.55(q,J＝7.1Hz,2H),2.62(s,3H),2.38(s,3H),1.48(t,J＝7.1Hz,3H).
Example 14
Under the illumination condition, 3, 4-dimethylbenzaldehyde (1mmol), diazo trivalence iodine reagent 1(1.5mmol) and dichloromethylThe alkane (2mL) was added to a 15mL test tube, reacted at room temperature for 15 hours, and separated by silica gel column chromatography to give the desired compound 3n in 65% yield. 1 H NMR(400MHz,CDCl 3 )δ7.95(s,1H),7.89-7.87(m,1H),7.24(d,J＝7.8Hz,1H),4.55(q,J＝7.1Hz,2H),2.62(s,3H),2.38(s,3H),1.48(t,J＝7.1Hz,3H).
Example 15
Under the illumination condition, 2,4, 6-trimethylbenzaldehyde (1mmol), diazo trivalent iodine reagent 1(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography is carried out to separate, so that the yield of the target compound 3o is 48%. 1 H NMR(400MHz,CDCl 3 )δ6.97(s,2H),4.54(q,J＝7.1Hz,2H),2.34(s,3H),2.27(s,6H),1.48(t,J＝7.1Hz,3H).
Example 16
Under the illumination condition, 3-methoxybenzaldehyde (1mmol), diazo trivalent iodine reagent 2(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the yield of the target compound 3p, wherein the yield is 87%. 1 H NMR(400MHz,CDCl 3 )δ8.05(d,J＝8.8Hz,2H),6.99(d,J＝8.8Hz,2H),4.06(s,3H),3.86(s,3H).
Example 17
Under the illumination condition, 3-methoxybenzaldehyde (1mmol), diazo trivalent iodine reagent 3(1.5mmol) and dichloromethane (2mL) are added into a 15mL test tube, the reaction is carried out for 15 hours at room temperature, and silica gel column chromatography separation is carried out to obtain the yield of the target compound 3q, wherein the yield is 78%. 1 H NMR(400MHz,CDCl 3 )δ 1 H NMR(500MHz,CDCl 3 )δ8.01(d,J＝6.9Hz,2H),7.43-7.41(m,2H),7.33-7.31(m,3H),6.93(d,J＝6.9Hz,2H),5.42(s,2H),3.81(s,3H).
Comparative example 1
Benzaldehyde (1mmol), a diazo trivalent iodine reagent (1.2mmol) and dichloromethane (2mL) are added into a 15mL test tube under the condition of keeping out of the light, and the reaction is carried out for 12 hours at room temperature, so that the target compound cannot be obtained.
Comparative example 2
Under the illumination condition, benzaldehyde (1mmol), a photocatalyst rhodamine B (10% mmol), a diazo trivalent iodine reagent 1(1.2mmol) and dichloromethane (2mL) are added into a 15mL test tube and react for 12 hours at room temperature to obtain the target compound 3a with the yield of 72%.
Claims (3)
1. A synthetic method of a 1,3, 4-oxadiazole heterocyclic compound is characterized in that benzaldehyde derivatives and trivalent iodine reagents are used as raw materials, and the raw materials are added into a solvent to be stirred and react to generate the 1,3, 4-oxadiazole heterocyclic derivatives; the stirring reaction conditions are as follows: reacting at room temperature under the condition of illumination, wherein the reaction time is 10-15 hours;
the structure of the trivalent iodine is shown as the following formula,
wherein R is 1 ＝COOEt，COOMe，COOCH 2 Ph；
The benzaldehyde derivative is as follows: benzaldehyde, 4-fluorobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehyde, 4-methylbenzaldehyde, 4-methoxybenzaldehyde, 4-t-butylbenzaldehyde, 3-methoxybenzaldehyde, 2-cyanobenzaldehyde, 2, 4-dimethoxybenzaldehyde, 2, 6-dichlorobenzaldehyde, 2, 4-dichlorobenzaldehyde, 2, 3-dimethylbenzaldehyde, 3, 4-dimethylbenzaldehyde, 2,4, 6-trimethylbenzaldehyde.
2. The method for synthesizing a 1,3, 4-oxadiazole heterocyclic compound according to claim 1, wherein the solvent is dichloromethane, chloroform, acetonitrile, or methanol.
3. The method for synthesizing a 1,3, 4-oxadiazole heterocyclic compound of claim 1, wherein the molar ratio of the benzaldehyde derivative to the trivalent iodine reagent is 1: 1.5.
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