CN112159375A - Green preparation method of 2, 3-dihydrofuran compound - Google Patents
Green preparation method of 2, 3-dihydrofuran compound Download PDFInfo
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- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
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Abstract
The invention relates to a green method for preparing 2, 3-dihydrofuran compounds from 1, 3-dicarbonyl compounds through halogen cyclization reaction without any additive system, wherein the reaction is carried out in aqueous solution at room temperature in the open air. The method comprises the steps of adding a 1, 3-dicarbonyl compound, a halogenating reagent and a solvent into a Schlenk reaction bottle, and stirring at room temperature for reaction to obtain a target product.
Description
Technical Field
The application belongs to the field of organic synthesis, and particularly relates to a green method for preparing 2, 3-dihydrofuran compounds from 1, 3-dicarbonyl compounds through halogen cyclization reaction without any additive system, wherein the reaction can be carried out in water solution at room temperature in the open air.
Background
Water, of low cost, safe, non-toxic and environmentally friendly nature, is certainly the most attractive chemical reaction medium in the green and sustainable chemical field. In addition, dimethyl sulfoxide (DMSO) is used as a general green solvent, and provides a wider space for the development of green organic reaction. On the other hand, the realization of organic reactions in air open at room temperature is one of the most desirable methods, since costs and energy consumption can be minimized. Therefore, organic transformations in water/DMSO mixed media open in air at room temperature are an attractive but challenging goal.
Electrophilic halocyclization of olefins has become an efficient strategy for the efficient preparation of cyclic compounds by introducing new halogen groups and generating new rings. In this context, there have been numerous investigations into the halocyclization of 1, 3-dicarbonyl compounds having allyl substitution. However, from the viewpoint of ecological friendliness and practicality, these achievements are still plagued by some disadvantages, such as the use of catalysts, the necessity of bases or oxidizing agents in the reaction, the need for higher reaction temperatures or toxic organic solvents. The present inventors have made intensive studies on the halocyclization reaction of a 1, 3-dicarbonyl compound, and in the present invention, we have proposed a halocyclization reaction method which can be carried out in an aqueous solution at room temperature in the open air. The method does not need to use any additive, and the reaction condition is mild and green.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for preparing 2, 3-dihydrofuran compounds from 1, 3-dicarbonyl compounds through halogen cyclization reaction, which is green, efficient and low in cost, does not need any additive, and can be used for preparing target products mildly with high yield.
The invention provides a halo cyclization reaction method, which takes a 1, 3-dicarbonyl compound and a halogenating reagent as raw materials and is prepared by the following steps:
adding a 1, 3-dicarbonyl compound shown in formula 1, a halogenating reagent shown in formula 2 and a solvent into a Schlenk reaction bottle, placing the reaction bottle at room temperature, stirring for reaction, monitoring the reaction progress by TLC or GC until the raw materials are completely reacted, and carrying out post-treatment to obtain a halogen cyclization product 2, 3-dihydrofuran (I).
The chemical reaction formula of the method for the halocyclization reaction of the 1, 3-dicarbonyl compound and the halogenating reagent provided by the invention can be expressed as (see formula I):
the post-processing operation is as follows: extracting the reaction solution after the reaction is finished with ethyl acetate, drying an organic phase with anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove a solvent, and separating the residue by column chromatography, wherein the elution solvent is: ethyl acetate/n-hexane to give 2, 3-dihydrofuran (I).
In the compounds represented by formula 1 and formula I, R1Is selected from C5-C14Aryl radical, C1-C10An alkyl group;
R2is selected from C5-C14Aryl radical, C1-C10An alkyl group;
R3is selected from C5-C14Aryl radical, C1-C10Alkyl radical, C1-C6An ester group;
[X]selected from N-iodosuccinimide (NIS), trimethyl iodosilane (TMSI), iodine simple substance (I)2) Iodine chloride (ICl), N-bromosuccinimide (NBS);
wherein each R is1-R3The aryl and alkyl groups having the number of carbon atoms in the substituents are optionally substituted by a substituent selected from the group consisting of halogen, C1-C6Alkyl radical, C1-C6Alkoxy radical, C5-C14Aryl, halogen substituted C1-C6Alkyl, -NO2、-CN、C1-C6alkyl-C (═ O) -, C1-C6alkyl-OC (O ═ O) -.
Preferably, R1Is selected from C1Alkyl radical, C5-C14An aryl group;
R2is selected from C1Alkyl radical, C5-C14An aryl group;
R3is selected from C1Alkyl radical, C6Aryl radical, C1-C6An ester group.
In the reaction of the present invention, the solvent is selected from any one of a mixed solvent of dimethyl sulfoxide (DMSO)/water, Tetrahydrofuran (THF)/water, ethanol (EtOH)/water, and ethyl acetate (EtOAc)/water, and is preferably dimethyl sulfoxide (DMSO)/water.
In the reaction of the present invention, the amount of water in the mixed solvent of dimethyl sulfoxide (DMSO)/water is 1.5mL, and the amount of DMSO is 0.2-0.6mL, preferably 0.5 mL.
In the reaction of the present invention, the halogenating agent is used in an amount of 1.2 to 2 equivalents, preferably 1.2 equivalents.
The invention has the beneficial effects that: a process for preparing 2, 3-dihydrofurans from 1, 3-dicarbonyl compound and halogenating reagent by halocyclization reaction features that the reaction can be carried out in aqueous solution at room temp in air without any additive and a series of target products can be obtained in high yield. The method has the advantages of wide reaction substrate application range, greenness and high efficiency, and is particularly suitable for industrial production.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the present invention is not limited thereto.
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and starting materials, if not otherwise specified, are commercially available and/or may be prepared according to known methods.
Examples 1-7 are experiments optimized for reaction conditions.
Example 1
A Schlenk flask was charged with a compound of formula 1a (55.6mg, 0.2mmol), a halogenating agent of formula 2a (54.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is finished, extracting the reaction liquid by using ethyl acetate, drying an organic phase by using anhydrous sodium sulfate, filtering and concentrating under reduced pressure to remove a solvent, and carrying out column chromatography separation on the residue (an elution solvent is ethyl acetate/n-hexane) to obtain a target product I-1 (95% yield);1H NMR(500MHz，CDCl3)：7.37-7.36(m，2H)，7.18-7.08(m，4H)，7.00-6.96(m，4H)，3.50-3.43(m，2H)，3.25-3.14(m，2H)，1.67(s，3H)；13C NMR(125MHz，CDCl3)：193.4，164.4，138.9，131.2，130.1，130.0，129.3，129.0，127.7，111.9，85.2，44.2，26.2，15.0。
example 2
The amount of the halogenating agent NIS used was 2.0eq (90.0mg), and the other conditions were the same as in example 1, whereby the yield of the objective product I-1 was 96%.
Example 3
The DMSO content was 0.2mL, and the yield of the target product I-1 was 20% under the same conditions as in example 1.
Example 4
The DMSO content was 0.6mL, and the yield of the target product I-1 was 95% under the same conditions as in example 1.
Example 5
The DMSO/water mixed solvent was replaced by a THF/water mixed solvent under the same conditions as in example 1 to obtain the desired product I-1 in a yield of 61%.
Example 6
The DMSO/water mixed solvent was replaced by EtOH/water mixed solvent, and the other conditions were the same as in example 1, to obtain the desired product I-1 with a yield of 88%.
Example 7
The DMSO/water mixed solvent was replaced by EtOAc/water mixed solvent under the same conditions as in example 1 to obtain the desired product I-1 in a yield of 91%.
As can be seen from the above examples 1-7, the optimum reaction conditions were those of example 1, i.e., the amount of halogenating agent NIS used was 1.2eq (54.0mg), DMSO/H2O (0.5mL/1.5mL) was used as a mixed solvent, and then the reactor was reacted at room temperature. On the basis of obtaining the optimal reaction condition, the inventor further selects 1, 3-dicarbonyl compounds with different substituents and halogenating reagents as raw materials under the optimal reaction condition to develop a method for preparing 2, 3-dihydrofuran compounds by green halocyclization reaction.
Example 8
A Schlenk flask was charged with a compound of formula 1a (55.6mg, 0.2mmol), a halogenating agent of formula 2b (48.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is finished, extracting the reaction liquid by ethyl acetate, drying the organic phase by anhydrous sodium sulfate, filtering and decompressing and concentrating to remove the solvent, and separating the residue by column chromatography (the elution solvent is ethyl acetate/n-hexane) to obtain the target product I-1 (13% yield).
Example 9
A Schlenk flask was charged with a compound of formula 1a (55.6mg, 0.2mmol), a halogenating agent of formula 2c (61.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is completed, extracting the reaction liquid with ethyl acetate, drying the organic phase with anhydrous sodium sulfate, filtering and concentrating under reduced pressure to remove the solvent, and separating the residue by column chromatography (the elution solvent is ethyl acetate/n-hexane) to obtain the target product I-1 (89% yield).
Example 10
To a Schlenk flask was added a compound of formula 1a (55.6mg, 0.2mmol), a halogenating agent of formula 2d (38.9mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), stirring the reactor at room temperature, monitoring the reaction progress by TLC until the raw material disappears (reaction time is 8 hours), extracting the reaction solution with ethyl acetate after the reaction is completed, drying the organic phase with anhydrous sodium sulfate, filtering and concentrating under reduced pressure to remove the solvent, and separating the residue by column chromatography (elution solvent: ethyl acetate/n-hexane)Alkane) to obtain the target product I-1 (32% yield).
Example 11
To a Schlenk flask was added a compound of formula 1a (55.6mg, 0.2mmol), a halogenating agent of formula 2e (42.7mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is finished, extracting the reaction liquid by ethyl acetate, drying an organic phase by anhydrous sodium sulfate, filtering and decompressing and concentrating to remove a solvent, and separating the residue by column chromatography (an elution solvent is ethyl acetate/n-hexane) to obtain a target product I-2 (72% yield);1H NMR(500MHz，CDCl3)：7.44-7.42(m，2H)，7.21-7.16(m，4H)，7.09-7.04(m，4H)，3.70-3.61(m，2H)，3.38(d，J＝19.5Hz，1H)，3.20(d，J＝19.0Hz，1H)，1.71(s，3H)；13C NMR(125MHz，CDCl3)：193.5，164.5，138.9，131.2，130.2，130.1，129.9，129.3，128.9，127.7，111.8，85.6，43.1，39.7，25.4。
example 12
A Schlenk flask was charged with a compound of formula 1b (76.4mg, 0.2mmol), a halogenating agent of formula 2a (54.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is finished, extracting the reaction liquid by ethyl acetate, drying an organic phase by anhydrous sodium sulfate, filtering and decompressing and concentrating to remove a solvent, and separating the residue by column chromatography (an elution solvent is ethyl acetate/n-hexane) to obtain a target product I-3 (96% yield); yellow oil (0.0975g, 96% yield);1H NMR(500MHz，CDCl3)：8.02-8.01(m，4H)，6.94-6.89(m，4H)，3.86(d，J＝6.0Hz，2H)，3.84(s，6H)，3.77(s，3H)，3.74(d，J＝7.0Hz，1H)，3.08(d，J＝6.5Hz，1H)；13C NMR(125MHz，CDCl3)：194.1，173.8，167.5，163.9，163.8，136.5，131.4，131.2，130.0，129.7，129.1，114.0，85.7，55.5，54.7，51.9，32.6，14.1。
example 13
A Schlenk flask was charged with a compound of formula 1c (43.2mg, 0.2mmol), a halogenating agent of formula 2a (54.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is completed, extracting the reaction solution with ethyl acetate, drying the organic phase with anhydrous sodium sulfate, filtering and concentrating under reduced pressure to remove the solvent, and separating the residue by column chromatography (the elution solvent is ethyl acetate/n-hexane) to obtain the target products I-4 and I-4' (I-4: I-4 ═ 2: 1, 78% yield);1H NMR(500MHz，CDCl3)：7.60-7.57(m，2H)，7.50-7.44(m，3H)，3.49-3.41(m，2H)，3.21-3.13(m，1H)，3.04-2.95(m，1H)，1.98(s，1H)，1.85(s，2H)，1.70(s，1H)，1.64(s，2H)；13C NMR(125MHz，CDCl3)：194.8，193.2，167.8，165.5，140.6，131.2，130.8，130.7，129.2，128.4，128.3，127.8，114.6，112.3，85.8，85.7，42.8，42.6，28.8，26.2，26.1，15.7，15.0。
example 14
To a Schlenk flask was added a compound of formula 1d (58.6mg, 0.2mmol), a halogenating agent of formula 2a (54.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then the reactor was stirred at room temperature and the progress of the reaction was monitored by TLCWhen the raw materials disappear (the reaction time is 8 hours), after the reaction is finished, extracting the reaction liquid by ethyl acetate, drying an organic phase by anhydrous sodium sulfate, filtering and concentrating under reduced pressure to remove a solvent, and separating the residue by column chromatography (the elution solvent is ethyl acetate/n-hexane) to obtain target products I-5 and I-5 '(I-5: I-5' ═ 4: 1, 73% yield);1H NMR(500MHz，CDCl3)：8.08(t，J＝7.5Hz，0.8H)，7.67-7.66(m，2H)，7.52-7.47(m，3H)，7.23(d，J＝4.0Hz，3H)，7.04-7.01(m，1.2H)，3.53-3.47(m，2H)，3.25(d，J＝15.5Hz，1H)，3.11(d，J＝15.5Hz，1H)，1.76(s，0.6H)，1.70(s，2.4H)；13C NMR(125MHz，CDCl3)：192.4，162.8，158.5，138.0，135.3，134.2(2)，131.1，130.9，129.9，129.7(2)，129.1，128.9，128.8(2)，128.6，127.6，123.8，119.2，106.8，84.7，43.3，26.1，15.1。
example 15
A Sehlenk flask was charged with a compound of formula 1e (68.0mg, 0.2mmol), a halogenating agent of formula 2a (54.0mg, 0.24mmol), DMSO/H2O (0.5mL/1.5mL), then stirring the reactor at room temperature for reaction, monitoring the reaction progress by TLC until the raw material disappears (the reaction time is 8 hours), after the reaction is finished, extracting the reaction liquid by ethyl acetate, drying an organic phase by anhydrous sodium sulfate, filtering and decompressing and concentrating to remove a solvent, and separating the residue by column chromatography (an elution solvent is ethyl acetate/n-hexane) to obtain a target product I-6 (85% yield);1H NMR(500MHz，CDCl3)：7.51(d，J＝7.5Hz，2H)，7.46(d，J＝7.0Hz，2H)，7.42(t，J＝8.0Hz，2H)，7.35(t，J＝8.0Hz，3H)，7.22(t，J＝7.5Hz，2H)，7.13-7.07(m，4H)，3.80-3.77(m，2H)，3.75(d，J＝3.0Hz，1H)，3.71(d，J＝15.5Hz，1H)；13C NMR(125MHz，CDCl3)：193.0，164.1，142.5，138.8，131.3，130.2，129.8，129.4，129.0，128.8，128.2，127.7(2)，125.0，112.2，87.5，45.4，16.9。
example 16 reaction mechanism control experiment
To further verify the reaction mechanism of this reaction, the following two sets of control experiments were performed. By adding 2.0 equivalents of tetramethylpiperidine nitroxide (TEMPO) or 2, 6-di-tert-butyl-4-methylphenol (BHT) as a radical scavenger to the reaction of example 1, the desired product was still obtained in 77% and 88% yields, respectively, eliminating the possibility of the reaction going through a radical reaction process.
It follows that the possible reaction mechanism of the present invention can be deduced as shown in the following formula:
the embodiments described above are only preferred embodiments of the invention and are not exhaustive of the possible implementations of the invention. Any obvious modifications to the above would be obvious to those of ordinary skill in the art, but would not bring the invention so modified beyond the spirit and scope of the present invention.
Claims (6)
1. A method for preparing 2, 3-dihydrofuran compounds from 1, 3-dicarbonyl compounds through halogen cyclization reaction is characterized by comprising the following steps:
adding a 1, 3-dicarbonyl compound shown in a formula 1, a halogenating reagent shown in a formula 2 and a solvent into a Schlenk reaction bottle, placing the reaction bottle at room temperature, stirring for reaction, monitoring the reaction process by TLC or GC until the raw materials are completely reacted, and carrying out post-treatment to obtain a halogen cyclization product 2, 3-dihydrofuran (I);
in the compounds represented by formula 1 and formula I, R1Is selected from C5-C14Aryl radical, C1-C10An alkyl group;
R2is selected from C5-C14Aryl radical, C1-C10An alkyl group;
R3is selected from C5-C14Aryl radical, C1-C10Alkyl radical, C1-C6An ester group;
[X]selected from N-iodosuccinimide (NIS), trimethyl iodosilane (TMSI), iodine simple substance (I)2) Iodine chloride (ICl), N-bromosuccinimide (NBS);
wherein each R is1-R3The aryl and alkyl groups having the number of carbon atoms in the substituents are optionally substituted by a substituent selected from the group consisting of halogen, C1-C6Alkyl radical, C1-C6Alkoxy radical, C5-C14Aryl, halogen substituted C1-C6Alkyl, -NO2、-CN、C1-C6alkyl-C (═ O) -, C1-C6alkyl-OC (O ═ O) -.
2. The method of claim 1, wherein R is1Is selected from C1Alkyl radical, C5-C14An aryl group;
R2is selected from C1Alkyl radical, C5-C14An aryl group;
R3is selected from C1Alkyl radical, C6Aryl radical, C1-C6An ester group.
3. The method according to any one of claims 1 to 2, wherein the solvent is selected from any one of a mixed solvent of Dimethylsulfoxide (DMSO)/water, Tetrahydrofuran (THF)/water, ethanol (EtOH)/water, and ethyl acetate (EtOAc)/water, preferably Dimethylsulfoxide (DMSO)/water.
4. The method according to claim 3, wherein the amount of water in the mixed solvent of dimethyl sulfoxide (DMSO)/water is 1.5mL, and the amount of DMSO is 0.2-0.6mL, preferably 0.5 mL.
5. The process according to any one of claims 1 to 4, characterized in that the halogenating agent is used in an amount of 1.2 to 2 equivalents, preferably 1.2 equivalents.
6. The method according to any of claims 1-5, characterized in that the post-processing operation is as follows: extracting the reaction solution after the reaction is finished with ethyl acetate, drying an organic phase with anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove a solvent, and separating the residue by column chromatography, wherein the elution solvent is: ethyl acetate/n-hexane to give 2, 3-dihydrofuran (I).
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