CN112441987A - Synthesis method of halogen oxazoline compound - Google Patents
Synthesis method of halogen oxazoline compound Download PDFInfo
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- CN112441987A CN112441987A CN201910821829.0A CN201910821829A CN112441987A CN 112441987 A CN112441987 A CN 112441987A CN 201910821829 A CN201910821829 A CN 201910821829A CN 112441987 A CN112441987 A CN 112441987A
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings 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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Abstract
The invention discloses a synthesis method of a halogen oxazoline compound, which comprises the following steps: adding N-allyl benzamide, potassium halide, potassium hydrogen persulfate composite salt and a solvent into a reaction bottle, stirring and mixing uniformly at room temperature, placing the mixture into an ice water bath for reaction, and after the raw materials react completely, washing, extracting, separating, rotary steaming and purifying to obtain a halogen oxazoline compound; the solvent is acetonitrile and water. Compared with the prior art, the preparation method has the advantages that the N-allyl benzamide is used as the raw material, the halogenated oxazoline is constructed in a one-pot method under the action of the potassium hydrogen persulfate composite salt and the potassium halide, the preparation method is simple and convenient to operate, environment-friendly, mild in condition, high in yield, relatively easy in aftertreatment, and suitable for large-scale preparation; the halogen atom of the prepared halogen oxazoline compound is an active derivative site, and a plurality of oxazoline derivatives can be prepared through nucleophilic substitution reaction.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of a halogen oxazoline compound.
Background
Oxazoline is an important five-membered heterocyclic structure, the skeleton of the oxazoline is widely present in a plurality of compound molecules with broad-spectrum pharmacological activity and biological activity, and the oxazoline compound is widely applied to the research and development of medicaments such as antimalarial, anticancer, antidepressant, antibacterial organisms and the like. In addition, in the field of organic synthesis, an oxazoline framework is also an important structural unit and is widely applied to the aspects of group protection, chiral ligands, chiral auxiliaries and the like.
Therefore, an efficient synthesis method of oxazoline is one of research hotspots of people, the reported methods mainly use a copper halide system, an iodobenzene acetate/trimethyl silicon iodide system, electrocatalysis, photocatalysis and other modes to construct a final oxazoline ring, the methods have certain significance and good substrate universality, but the methods may generate heavy metal residues and generate more organic three wastes, or special devices are needed, so that the wide application of the methods is limited.
Disclosure of Invention
At present, a one-pot method is not reported in the methods for synthesizing oxazoline compounds at home and abroad, and in order to solve the problems, the invention provides a method for synthesizing halogen oxazoline compounds, which adopts the one-pot method to provide a new method for constructing an oxazoline ring which is environment-friendly and simple and convenient to operate, the method is carried out in an air atmosphere, the used solvent is water and acetonitrile which has small influence on the environment, the used oxidant and halogenating agent are inorganic salts which are cheap and easy to obtain, the generated by-product is only inorganic salt potassium sulfate, and the method provides a good reference for drug synthesis of oxazoline, so that the method has very wide research and development prospects.
The object of the invention is achieved in the following way:
a synthetic method of a halogen oxazoline compound comprises the following steps: adding N-allyl benzamide, potassium halide, potassium hydrogen persulfate composite salt and a solvent into a reaction bottle, stirring and mixing uniformly at room temperature, placing the mixture into an ice water bath for reaction, and after the raw materials react completely, washing, extracting, separating, rotary steaming and purifying to obtain a halogen oxazoline compound; the solvent is acetonitrile and water; the reaction formula is as follows:
the feeding molar ratio of the N-allyl benzamide to the potassium halide to the potassium hydrogen persulfate composite salt is 1 (4-6) to 2-3.
The dosage of the solvent is 10 times of the mass of the N-allyl benzamide, wherein the volume ratio of the acetonitrile to the water is 1: 1.
And R is any one of 2-methyl, 3-methyl, 4-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 2-fluoro, 4-fluoro, 2-nitro, 3-nitro, 4-phenyl, 4-ethyl, 4-tert-butyl, 3-bromo, 4-bromo or 4-chloro.
The reaction time in the ice-water bath is 4-6 h.
The extraction was performed by ethyl acetate.
Compared with the prior art, the preparation method has the advantages that the N-allyl benzamide is used as the raw material, the halogenated oxazoline is constructed in a one-pot method under the action of the potassium hydrogen persulfate composite salt and the potassium halide, the preparation method is simple and convenient to operate, environment-friendly, mild in condition, high in yield, relatively easy in aftertreatment, and suitable for large-scale preparation; the halogen atom of the prepared halogen oxazoline compound is a derivative site with chemical activity, and a plurality of oxazoline derivatives can be prepared through nucleophilic substitution reaction; the yield of the invention can reach 98.8%.
Drawings
FIG. 1 is a NMR spectrum of product 2c of example 3.
FIG. 2 is a NMR carbon spectrum of product 2c of example 3.
FIG. 3 is a high resolution mass spectrum of product 2c from example 3.
FIG. 4 is a NMR spectrum of product 2f of example 6.
FIG. 5 is a NMR carbon spectrum of product 2f of example 6.
FIG. 6 is a high resolution mass spectrum of product 2f of example 6.
FIG. 7 is a NMR spectrum of 2g of the product of example 7.
FIG. 8 is a NMR carbon spectrum of 2g of the product of example 7.
FIG. 9 is a high resolution mass spectrum of 2g of the product of example 7.
Detailed Description
A synthetic method of a halogen oxazoline compound comprises the following steps: adding N-allyl benzamide, potassium halide, potassium hydrogen persulfate composite salt and a solvent into a reaction bottle, stirring and mixing uniformly at room temperature, placing the mixture into an ice water bath for reaction, and after the raw materials react completely, washing, extracting, separating, rotary steaming and purifying to obtain a halogen oxazoline compound; the solvent is acetonitrile and water; the reaction formula is as follows:
furthermore, the feeding molar ratio of the N-allyl benzamide to the potassium halide to the oxone composite salt is 1 (4-6) to (2-3). The potassium hydrogen persulfate composite salt is KHSO5-KHSO4-K2SO 4.
Further, the amount of the solvent is 10 times of the mass of the N-allyl benzamide, wherein the volume ratio of the acetonitrile to the water is 1: 1.
Further, R is any one of 2-methyl, 3-methyl, 4-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 2-fluoro, 4-fluoro, 2-nitro, 3-nitro, 4-phenyl, 4-ethyl, 4-tert-butyl, 3-bromo, 4-bromo or 4-chloro.
Further, the reaction time in the ice-water bath is 4-6 h.
Further, the extraction is performed by ethyl acetate. The washing, extracting, separating, rotary steaming and purifying processes are as follows: after the raw materials are completely reacted through TLC detection, 50mL of water and 30mL of ethyl acetate are added into the system, liquid separation is carried out, the water phase is extracted twice by ethyl acetate, the organic phase is combined, anhydrous MgSO4 is dried, rotary evaporation and concentration are carried out, column chromatography is carried out on the residue, eluent in the column chromatography process is a petroleum ether/ethyl acetate mixture, and the volume ratio of the petroleum ether to the ethyl acetate is 4: 1.
The invention will be further illustrated with reference to specific examples:
example 1
The synthesis equation in this embodiment is:
1.75g (10mmol) of N-allyl-2-methylbenzamide 1a, 8.3g (50mmol) of potassium iodide, 12.3g (20mmol) of potassium hydrogen persulfate complex salt, 10mL of acetonitrile and 10mL of water are added into a 100mL reaction bottle, wherein the total mass of the solvent is 17.9 g, the mixture is stirred and mixed uniformly at room temperature and then placed into an ice water bath for reaction for 5 hours, after the TLC detection of the complete reaction of raw materials, 50mL of water and 30mL of ethyl acetate are added into the system, liquid separation is carried out, an aqueous phase is extracted twice by ethyl acetate, organic phases are combined, anhydrous MgSO4 is dried and rotary evaporation and concentration are carried out, the residue is subjected to column chromatography, and eluent in the column chromatography is a mixture of petroleum ether and ethyl acetate, the ratio of the mixture is 4:1, so that 2.81g of the corresponding target product 2a is obtained, and the yield is 93.3%.
The detection spectrum data of the product are as follows: 1H NMR (400MHz, CDCl3) δ 7.81(d, J8.0 Hz,1H),7.36-7.31(m,1H),7.24-7.20(m,2H),4.73-4.70(m,1H),4.22-4.14(m,1H),3.85-3.80(m,1H),3.35-3.32(m,2H),2.60(s,3H), 13CNMR (100MHz, CDCl3) δ 13C NMR (100MHz, CDCl3) δ 163.8,138.8,131.2,130.7,129.8,126.7,125.5,77.3,61.0,21.9,8.1. this is consistent with standard spectral data.
Example 2
The synthesis equation in this embodiment is:
the same synthesis as in example 1, except that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1b to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 5: 2, 2.70g of the target product 2b was obtained as a white solid with a yield of 88.6%.
The detection spectrum data of the product are as follows: 1H NMR (400MHz, CDCl3) δ 7.94-7.90(m,2H),7.08(t, J ═ 8.8Hz,2H),4.81-4.77(m,1H),4.15(dd, J ═ 9.6,15.2Hz,1H),3.78(dd, J ═ 6.8,15.2Hz,1H),3.38-3.29(m,2H), 13C NMR (100MHz, CDCl3) δ 166.0,163.5,162.5,130.4,130.4,123.6,123.6,115.6,115.4,78.4,60.7,7.6.19F 376 (MHz, CDCl3) δ ═ -107.8.
Example 3
The synthesis equation in this embodiment is:
the same synthesis as in example 1, except that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1c to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 5: 2, the objective product 2c 2.70g was obtained as an oily liquid with a yield of 81.3%.
The detection spectrum data of the product 2c are as follows: 1H NMR (400MHz, CDCl3) δ 7.86(dd, J ═ 8.0,8.0Hz,2H),7.67-7.62(M,2H),4.88-4.84(M,1H),4.20(dd, J ═ 12.0,9.0Hz,1H),3.86(dd, J ═ 8.0,4.0Hz,1H),3.40-3.31(M,2H), 13C NMR (100MHz, CDCl3) δ 160.7,148.8,132.5,131.5,131.0,123.8,122.7,79.2,60.8,6.9 HRMS-ESI (M/z) [ M + H ] + calcd for C11H12INO2,332.9736, found 332.9729. The spectral data for product 2c are shown in FIGS. 1-3, which are consistent with the structure of product 2 c.
Example 4
The synthesis equation in this embodiment is:
the same synthesis as in example 1, except that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1d to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 5: 2, the desired product 2d was obtained in 3.32g, white solid, yield 90.9%.
The detection spectrum data of the product are as follows: 1H NMR (400MHz, CDCl3) δ 7.78(d, J ═ 8.0Hz,2H),7.54(d, J ═ 8.0Hz,2H),4.82-4.75(m,1H),4.15(q, J ═ 8.0Hz,1H),3.75(q, J ═ 8.0Hz,1H),3.38-3.29(m,2H), 13C NMR (100MHz, CDCl3) δ 162.6,131.6,129.6,126.3,126.2,78.4,60.8,7.6.
Example 5
The synthesis equation in this embodiment is:
the same synthesis as in example 1, except that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1e to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 5: 2, the desired product 2e was obtained in 3.25g, white solid, yield 94.8%. The melting point of the product is as follows: 104-106 ℃.
The detection spectrum data of the product are as follows: 1H NMR (400MHz, CDCl3) δ 7.86(d, J ═ 8.5Hz,2H),7.44(d, J ═ 8.6Hz,2H), 4.88-4.74 (m,1H),4.17(dd, J ═ 15.1,9.5Hz,1H),3.80(dd, J ═ 15.1,6.5Hz,1H),3.40-3.29(m,2H),1.33(s,9H), 13C NMR (100MHz, CDCl3) δ 163.3,154.8,127.9,125.2,124.5,78.0,60.6,34.8,31.0,7.8.
Example 6
The synthesis equation in this embodiment is:
the same synthesis as in example 1, except that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1f to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 5: 2, the target product 2f 3.59g is obtained as a white solid in 98.8% yield melting point: 107-109 ℃.
The detection spectrum data of the product 2f are as follows: 1H NMR (400MHz, CDCl3) δ 8.01(d, J ═ 2.0Hz,2H),7.67-7.62(M,4H),7.47(q, J ═ 7.6Hz,2H),7.39(q, J ═ 5.12Hz,1H),4.88-4.81(M,1H),4.21(q, J ═ 9.6Hz,1H),3.84(q, J ═ 8.4Hz,1H),3.43-3.33(M,2H), 13C NMR (100MHz, CDCl3) δ 163.4,144.2,140.1,128.9,128.6,127.9,127.2,127.0,126.2,60.8,7.7.HRMS-ESI (M/z) [ M + H ] + calcd for C16H14INO,364.0198, found 364.0197. its product 2f has the spectral data shown in fig. 4-6, which is consistent with the structure of product 2 f.
Example 7
The synthesis equation in this embodiment is:
the same synthesis as in example 1, except that: the feeding molar ratio of the N, N' -diallyl terephthalamide to the potassium iodide-potassium hydrogen persulfate composite salt is 1: 10: 4, this example corresponds to a bifunctional reaction, giving 2g 2.87g of the expected product, as a white solid, in 58.1% yield, melting point: 189 and 191 ℃.
The detection spectrum data of the product 2g are as follows: 1H NMR (400MHz in CDCl3) delta 7.98(s,4H),4.86-4.81(M,2H),4.24-4.17(M,2H),3.86-3.8(M,2H),3.41-3.32(M,4H).13C NMR (100MHz in CDCl3) delta 162.8,130.1,128.2,60.8,7.5 HRMS-ESI (M/z) [ M + H ] + calcd for C14H14I2N2O2,496.9223, found496.9197. the spectral data for 2g of product are shown in FIGS. 7-9, which is consistent with the structure of 2g of product.
Example 8
The synthesis equation in this embodiment is:
the difference from example 1 is that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1e to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 4: 3, the mass of the solvent is as follows: 17.8 g, the volume ratio of acetonitrile to water is 1:1, the reaction time is 4h, and the target product 2e 3.10g is obtained, white solid is obtained, and the yield is 90.5%.
Example 9
The synthesis equation in this embodiment is:
the difference from example 1 is that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1e to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 6: 3, the mass of the solvent is as follows: 17.8 g, the volume ratio of acetonitrile to water is 1:1, the reaction time is 4h, and the target product 2e 3.19g is obtained, white solid is obtained, and the yield is 93.2%.
Example 10
The synthesis equation in this embodiment is:
the difference from example 1 is that: the feeding molar ratio of the N-allyl-2-methylbenzamide 1e to the potassium iodide to the potassium hydrogen persulfate composite salt is 1: 6: 2, the mass of the solvent is as follows: 17.8 g, the volume ratio of acetonitrile to water is 1:1, the reaction time is 6h, and the target product 2e 2.94g is obtained, white solid is obtained, and the yield is 85.8%.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various changes and modifications can be made without departing from the overall concept of the invention, and these should be considered as the protection scope of the present invention, which will not affect the effect of the implementation of the present invention and the practicability of the patent.
Claims (6)
1. A synthetic method of a halogen oxazoline compound is characterized in that: the method comprises the following steps: adding N-allyl benzamide, potassium halide, potassium hydrogen persulfate composite salt and a solvent into a reaction bottle, stirring and mixing uniformly at room temperature, placing the mixture into an ice water bath for reaction, and after the raw materials react completely, washing, extracting, separating, rotary steaming and purifying to obtain a halogen oxazoline compound; the solvent is acetonitrile and water; the reaction formula is as follows:
2. the method for synthesizing a halogen oxazoline compound according to claim 1, comprising: the feeding molar ratio of the N-allyl benzamide to the potassium halide to the potassium hydrogen persulfate composite salt is 1 (4-6) to 2-3.
3. The method for synthesizing a halogen oxazoline compound according to claim 1, comprising: the dosage of the solvent is 10 times of the mass of the N-allyl benzamide, wherein the volume ratio of the acetonitrile to the water is 1: 1.
4. The method for synthesizing a halogen oxazoline compound according to claim 1, comprising: and R is any one of 2-methyl, 3-methyl, 4-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 2-fluoro, 4-fluoro, 2-nitro, 3-nitro, 4-phenyl, 4-ethyl, 4-tert-butyl, 3-bromo, 4-bromo or 4-chloro.
5. The method for synthesizing a halogen oxazoline compound according to claim 1, comprising: the reaction time in the ice-water bath is 4-6 h.
6. The method for synthesizing a halogen oxazoline compound according to claim 1, comprising: the extraction was performed by ethyl acetate.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005213168A (en) * | 2004-01-28 | 2005-08-11 | Kumiai Chem Ind Co Ltd | Isoxazolin-3-yl derivative and herbicide containing the same as active ingredient |
CN108586372A (en) * | 2018-05-03 | 2018-09-28 | 商丘师范学院 | A kind of synthetic method of 2- Fang oxazolin amide compounds |
CN110078723A (en) * | 2019-04-12 | 2019-08-02 | 上海师范大学 | Monosubstituted oxazolyl quinoline ring NNN class chirality pincer ligand and its metal complex and preparation method |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005213168A (en) * | 2004-01-28 | 2005-08-11 | Kumiai Chem Ind Co Ltd | Isoxazolin-3-yl derivative and herbicide containing the same as active ingredient |
CN108586372A (en) * | 2018-05-03 | 2018-09-28 | 商丘师范学院 | A kind of synthetic method of 2- Fang oxazolin amide compounds |
CN110078723A (en) * | 2019-04-12 | 2019-08-02 | 上海师范大学 | Monosubstituted oxazolyl quinoline ring NNN class chirality pincer ligand and its metal complex and preparation method |
Non-Patent Citations (4)
Title |
---|
CHUN-HUA YANG等: "CuBr2-promoted intramolecular bromocyclization of N-allylamides and aryl allyl ketone oximes", 《TETRAHEDRON》 * |
KATSUHIKO MORIYAMA等: "Oxidative oxygen-nucleophilic bromo-cyclization of alkenyl carbonyl compounds without organic wastes using alkali metal reagents in green solvent", 《RSC ADV.》 * |
WEI YI等: "Environmentally Friendly Protocol for the Oxidative Iodofunctionalization of Olefins in a Green Solvent", 《ACS SUSTAINABLE CHEM. ENG.》 * |
刘新明等: "KX/Oxone体系实现的N-烯丙基芳酰胺的氧化卤环化反应:5-卤甲基-2-噁唑啉的绿色合成", 《CHIN. J. ORG. CHEM.》 * |
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