CN115819366B - Preparation method of 2-aroyl substituted oxazole compound and compound prepared by same - Google Patents
Preparation method of 2-aroyl substituted oxazole compound and compound prepared by same Download PDFInfo
- Publication number
- CN115819366B CN115819366B CN202211452437.XA CN202211452437A CN115819366B CN 115819366 B CN115819366 B CN 115819366B CN 202211452437 A CN202211452437 A CN 202211452437A CN 115819366 B CN115819366 B CN 115819366B
- Authority
- CN
- China
- Prior art keywords
- potassium iodide
- preparation
- compound
- cdcl
- butyl hydroperoxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 oxazole compound Chemical class 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims abstract description 120
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 144
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 76
- 239000011734 sodium Substances 0.000 description 40
- 239000007787 solid Substances 0.000 description 25
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 239000007858 starting material Substances 0.000 description 16
- 150000002916 oxazoles Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 3
- GELOLSPOTXOQFL-UHFFFAOYSA-N phenyl-(5-phenyl-1,3-oxazol-2-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C(O1)=NC=C1C1=CC=CC=C1 GELOLSPOTXOQFL-UHFFFAOYSA-N 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical class N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Chemical class 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- RNJUEQIEGMCUJF-UHFFFAOYSA-N (2-oxo-2-thiophen-2-ylethyl)azanium;chloride Chemical compound Cl.NCC(=O)C1=CC=CS1 RNJUEQIEGMCUJF-UHFFFAOYSA-N 0.000 description 1
- GFHFMCRPNVXGFL-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=CC=C1F GFHFMCRPNVXGFL-UHFFFAOYSA-N 0.000 description 1
- NRLXHBFFYMPJPL-UHFFFAOYSA-N 2-amino-1-(2-methoxyphenyl)ethanone;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C(=O)CN NRLXHBFFYMPJPL-UHFFFAOYSA-N 0.000 description 1
- YAXCMTGQEHATRY-UHFFFAOYSA-N 2-amino-1-(3,4-difluorophenyl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=C(F)C(F)=C1 YAXCMTGQEHATRY-UHFFFAOYSA-N 0.000 description 1
- ZULGIQDFVVMFMI-UHFFFAOYSA-N 2-amino-1-(3,4-dimethoxyphenyl)ethanone;hydrochloride Chemical compound Cl.COC1=CC=C(C(=O)CN)C=C1OC ZULGIQDFVVMFMI-UHFFFAOYSA-N 0.000 description 1
- ORPJIXJTXWDVRY-UHFFFAOYSA-N 2-amino-1-(3-chlorophenyl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=CC(Cl)=C1 ORPJIXJTXWDVRY-UHFFFAOYSA-N 0.000 description 1
- KQFJTAPVOZRIIC-UHFFFAOYSA-N 2-amino-1-(4-ethylphenyl)ethanone;hydrochloride Chemical compound Cl.CCC1=CC=C(C(=O)CN)C=C1 KQFJTAPVOZRIIC-UHFFFAOYSA-N 0.000 description 1
- KQROOJFZQSQJMM-UHFFFAOYSA-N 2-amino-1-(4-fluorophenyl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=C(F)C=C1 KQROOJFZQSQJMM-UHFFFAOYSA-N 0.000 description 1
- FZVYWBMMOSHMRS-UHFFFAOYSA-N 2-amino-1-(4-methoxyphenyl)ethanone;hydrochloride Chemical compound Cl.COC1=CC=C(C(=O)CN)C=C1 FZVYWBMMOSHMRS-UHFFFAOYSA-N 0.000 description 1
- IHWOUORJQZGRRF-UHFFFAOYSA-N 2-amino-1-(4-methylphenyl)ethanone;hydrochloride Chemical compound Cl.CC1=CC=C(C(=O)CN)C=C1 IHWOUORJQZGRRF-UHFFFAOYSA-N 0.000 description 1
- RKEARERKYHKVQD-UHFFFAOYSA-N 2-amino-1-(furan-2-yl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=CO1 RKEARERKYHKVQD-UHFFFAOYSA-N 0.000 description 1
- APBKZMJARWKEJO-UHFFFAOYSA-N 2-amino-1-[4-(trifluoromethyl)phenyl]ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=C(C(F)(F)F)C=C1 APBKZMJARWKEJO-UHFFFAOYSA-N 0.000 description 1
- ABUOEFHIWKRZFK-UHFFFAOYSA-N 2-amino-1-naphthalen-2-ylethanone;hydrochloride Chemical compound [Cl-].C1=CC=CC2=CC(C(=O)C[NH3+])=CC=C21 ABUOEFHIWKRZFK-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- ILOIOIGZFHGSMS-UHFFFAOYSA-N 7-phenyl-1-(5-pyridin-2-yl-1,3-oxazol-2-yl)heptan-1-one Chemical compound N=1C=C(C=2N=CC=CC=2)OC=1C(=O)CCCCCCC1=CC=CC=C1 ILOIOIGZFHGSMS-UHFFFAOYSA-N 0.000 description 1
- UGIOQAMIEOSRLM-UHFFFAOYSA-N C1=CC(OC)=CC=C1C(=O)C1=NC=C(C=2C=CC(OC)=CC=2)O1 Chemical compound C1=CC(OC)=CC=C1C(=O)C1=NC=C(C=2C=CC(OC)=CC=2)O1 UGIOQAMIEOSRLM-UHFFFAOYSA-N 0.000 description 1
- UADIKUTXIHDRMX-UHFFFAOYSA-N [2-(2-nitrophenyl)-2-oxoethyl]azanium;chloride Chemical compound Cl.NCC(=O)C1=CC=CC=C1[N+]([O-])=O UADIKUTXIHDRMX-UHFFFAOYSA-N 0.000 description 1
- NHGCBHQCONRQKP-UHFFFAOYSA-N [2-(3-methoxyphenyl)-2-oxoethyl]azanium;chloride Chemical compound Cl.COC1=CC=CC(C(=O)CN)=C1 NHGCBHQCONRQKP-UHFFFAOYSA-N 0.000 description 1
- BRFUJSROKAAPJT-UHFFFAOYSA-N [2-(3-nitrophenyl)-2-oxoethyl]azanium;chloride Chemical compound Cl.NCC(=O)C1=CC=CC([N+]([O-])=O)=C1 BRFUJSROKAAPJT-UHFFFAOYSA-N 0.000 description 1
- ROAVTVXTYFSQEA-UHFFFAOYSA-N [2-(4-bromophenyl)-2-oxoethyl]azanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=C(Br)C=C1 ROAVTVXTYFSQEA-UHFFFAOYSA-N 0.000 description 1
- OVKMQHKVUWBLSV-UHFFFAOYSA-N [2-(4-chlorophenyl)-2-oxoethyl]azanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=C(Cl)C=C1 OVKMQHKVUWBLSV-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VGWHLCLCKMXXIQ-UHFFFAOYSA-N methyl 5-methoxy-1,3-oxazole-2-carboxylate Chemical compound COC(=O)C1=NC=C(OC)O1 VGWHLCLCKMXXIQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention belongs to the field of pharmaceutical chemistry, and in particular relates to a preparation method of a 2-aroyl substituted oxazole compound and a compound prepared by the same, wherein the method takes a 2-amino substituted aryl ethanone compound shown in a formula (I) as a raw material, takes tert-butyl hydroperoxide and potassium iodide as catalysts, and prepares the 2-ketone-1, 3-oxazole compound shown in a formula (II) by reaction, wherein the reaction equation is as follows:
Description
Technical Field
The invention belongs to the field of pharmaceutical chemistry, and particularly relates to a preparation method of a 2-aroyl substituted oxazole compound and a compound prepared by the same.
Background
The 2-aroyl substituted oxazole compound is an important nitrogen-oxygen heterocyclic compound, widely exists in various natural products, medicines and pesticides, and has very wide application prospect. For example, analgesic compound OL-135, anticancer compound 9, etc., which all contain 2-aroyl substituted oxazole compound key structure skeleton. Therefore, developing a synthetic route with high efficiency and low toxicity has considerable research value.
The current method for synthesizing 2-aroyl substituted oxazole compounds mainly comprises the following steps: the first method is to take substituted oxazole and carboxylic aryl ketone or halogenated aryl ketone as raw materials, and heat up the raw materials under the catalysis of heavy metals such as palladium, nickel and the like, and the method not only needs to use expensive heavy metal catalysts, but also needs to heat up the raw materials, thereby being not only unfavorable for post-reaction treatment, causing environmental pollution, wasting energy and not meeting the current requirements of environmental protection, energy conservation and environmental protection; the second is to take substituted ethylene and ammonium acetate as raw materials, to prepare the product by heating under the action of iodine and IBX, or to take beta-amino substituted aryl propionic acid as raw materials, to prepare the product by heating under the action of iodine and trifluoroacetic acid, and in either method, the product needs to be heated, which does not meet the energy-saving requirement.
In conclusion, the preparation method for the 2-aroyl substituted oxazole compound has important application prospect, and is energy-saving, economical and environment-friendly.
Disclosure of Invention
The invention aims to provide an energy-saving, economical and environment-friendly preparation method of 2-aroyl substituted oxazoles, which takes 2-amino substituted aryl ethanones as raw materials, tertiary butyl hydroperoxide and potassium iodide as catalysts, and prepares the 2-aroyl substituted oxazoles by reaction at normal temperature.
A second object of the present invention is to provide oxazoles prepared by the process of the present invention, which comprises (4- (trifluoromethyl) phenyl) (5- (4- (trifluoromethyl) phenyl) oxazol-2-yl) methanone, (3-chlorophenyl) (5- (3-chlorophenyl) oxazol-2-yl) methanone, (3-nitrophenyl) (5- (3-nitrophenyl) oxazol-2-yl) methanone, (2-methoxyphenyl) (5- (2-methoxyphenyl) oxazol-2-yl) methanone, (2-nitrophenyl) (5- (2-nitrophenyl) oxazol-2-yl) methanone, thiophen-2-yl (5- (thiophen-2-yl) oxazol-2-yl) methanone, furan-2-yl (5- (furan-2-yl) oxazol-2-yl) methanone, (3, 4-difluorophenyl) (5- (3, 4-difluorophenyl) oxazol-2-yl) methanone.
On the one hand, the invention provides a synthesis method of 2-aroyl substituted oxazoles, which takes 2-amino substituted aryl ethanone compound shown in formula (I) as raw material and tert-butyl hydroperoxide and potassium iodide as catalyst to react to prepare 2-ketone-1, 3-oxazoles shown in formula (II), wherein the reaction equation is as follows:
Wherein R is selected from aryl and substituted aryl.
In some preferred embodiments, R is selected from phenyl, p-nitrophenyl, p-trifluoromethylphenyl, p-methoxyphenyl, p-fluorophenyl, p-methylphenyl or m-chlorophenyl.
According to the synthesis method, the reaction temperature of the method is 20-40 ℃; preferably, the temperature is 25 ℃.
According to the synthesis method, the reaction time of the method is 2-8 h; preferably, the reaction time is 6h.
The inventor discovers that the existing method for synthesizing the 2-aroyl substituted oxazole compound needs to be heated, is unsafe and is unfavorable for reducing the industrial production cost, and the inventor surprisingly discovers that when the 2-amino substituted aryl ethanone compound is selected as a reaction raw material and is catalyzed by the addition of tert-butyl hydroperoxide and potassium iodide, the cyclization reaction can be carried out at the temperature of 20-40 ℃ to obtain the 2-aroyl substituted oxazole compound. In addition, the inventor discovers that the common reaction raw materials, such as substituted oxazole and carboxylic acid aryl ketone or halogenated aryl ketone, or substituted ethylene and ammonium acetate or beta-amino substituted aryl propionic acid, are selected, tertiary butyl hydroperoxide and potassium iodide are added for catalysis, various feeding molar ratios are tried, and no product is generated at normal temperature; when the 2-amino substituted aryl ethanone compound is used as a raw material, tert-butyl hydroperoxide or potassium iodide is independently added for catalysis, and no product is generated at normal temperature.
The inventors have also found that the ratio of t-butyl hydroperoxide to potassium iodide has a significant effect on the reaction yield. When the molar ratio of the tert-butyl hydroperoxide to the potassium iodide is 2:1-3:1, the byproduct is less formed, the post-treatment is easy, and the reaction yield is high. When the molar ratio of t-butyl hydroperoxide to potassium iodide is less than 2:1 or more than 3:1, the reaction product is less, the yield is low, and the byproducts are more and purification is difficult.
According to the synthesis method, the molar ratio of the tert-butyl hydroperoxide to the potassium iodide is 2:1-3:1; preferably, the molar ratio of the tert-butyl hydroperoxide to the potassium iodide is 3:1.
According to the synthesis method of the invention, the molar ratio of the compound of the formula (I) to the potassium iodide is 1:1-1:3, preferably the molar ratio of the compound of the formula (I) to the potassium iodide is 1:1.
In another aspect, the invention provides a compound prepared using the method of the invention, the compound selected from the group consisting of:
The compound provided by the invention can be used as an intermediate for synthesizing antibacterial, anticancer and anti-inflammatory drugs.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
EXAMPLE 1 preparation of phenyl (5-phenyloxazol-2-yl) methanone
To a 50mL eggplant-shaped bottle was added 2-aminoacetophenone hydrochloride (0.17 g,1.0 mmol), potassium iodide (0.16 g,1.0 mmol), tert-butyl hydroperoxide (0.38 g,3.0 mmol) and Ethyl Acetate (EA) 10mL, and the mixture was stirred at 25℃for about 6 hours. After completion of the reaction by thin layer chromatography, 10mL of a saturated sodium thiosulfate solution, 40mL of water and 50mL of ethyl acetate were added for extraction, and the organic layer was dried over anhydrous sodium sulfate and concentrated. The yellow solid is obtained by column chromatography purification after the solid is dried, and the yield is 78％.m.p.133-135℃;1HNMR(600MHz,CDCl3)δ8.48(d,J＝7.1Hz,2H),7.87-7.82(m,2H),7.65(t,J＝7.4Hz,1H),7.62(s,1H),7.54(t,J＝7.8Hz,2H),7.49(t,J＝7.5Hz,2H),7.43(t,J＝7.4Hz,1H);13C NMR(151MHz,CDCl3)δ178.66,157.09,154.21,135.41,133.73,130.77,129.97,129.12,128.46,126.77,125.43,123.91.HRMS(TOF):m/z[M+Na]+calculated for C16H11NO2Na:272.0687;found:272.0691.
EXAMPLE 2 preparation of (4- (trifluoromethyl) phenyl) (5- (4- (trifluoromethyl) phenyl) oxazol-2-yl) methanone Using 2-amino-1- (4- (trifluoromethyl) phenyl) ethanone hydrochloride, potassium iodide, tert-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the same procedure was followed as in example 1 to give a white solid in yield 80％.m.p.144-148℃;1H NMR(600MHz,CDCl3)δ8.62(d,J＝8.1Hz,2H),7.96(d,J＝8.1Hz,2H),7.82(d,J＝8.2Hz,2H),7.76(d,J＝8.2Hz,2H),7.74(s,1H);13C NMR(151MHz,CDCl3)δ177.38,157.11,153.06,137.81,135.20,132.04,131.14,129.73,126.28,126.26,125.68,125.47,124.57,122.76.HRMS(TOF):m/z[M+Na]+calculated for C18H9NO2F6Na:408.0435;found:408.0434.
EXAMPLE 3 preparation of thiophen-2-yl (5- (thiophen-2-yl) oxazol-2-yl) methanone
Using 2-amino-1- (thiophen-2-yl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a yellow solid .m.p.152-156℃;1HNMR(600MHz,CDCl3)δ8.59(dd,J＝3.9,1.1Hz,1H),7.79(dd,J＝4.9,1.1Hz,1H),7.55(dd,J＝3.6,0.9Hz,1H),7.46(dd,J＝5.0,1.1Hz,1H),7.45(s,1H),7.23(dd,J＝4.8,4.0Hz,1H),7.14(dd,J＝5.0,3.7Hz,1H).;13C NMR(151MHz,CDCl3)δ170.21,155.98,149.89,140.69,136.66,136.08,128.48,128.44,128.23,127.86,126.88,123.44.HRMS(TOF):m/z[M+Na]+calculated for C12H7NO2S2Na:283.9816;found:283.9821.
EXAMPLE 4 preparation of naphthalen-2-yl (5- (naphthalen-2-yl) oxazol-2-yl) methanone
Using 2-amino-1- (naphthalen-2-yl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a yellow solid .m.p.165-167℃;1HNMR(600MHz,CDCl3)δ9.27(s,1H),8.48–8.35(m,2H),8.08(d,J＝7.6Hz,1H),7.99–7.90(m,4H),7.88(d,J＝7.6Hz,2H),7.77(s,1H),7.65(s,1H),7.57(d,J＝14.1Hz,3H);13C NMR(151MHz,CDCl3)δ
178.42,157.35,154.33,135.95,133.84,133.74,133.29,132.69,132.49,130.19,129.02,128.98,128.60,128.30,127.90,127.79,127.33,127.07,126.77,125.51,125.13,124.35,124.01,122.39.HRMS(TOF):m/z[M+Na]+calculated for C24H15NO2Na:372.1000;
found:372.1004.
Example 5 preparation of (2-nitrophenyl) (5- (2-nitrophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (2-nitrophenyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a yellow solid .m.p.128-130℃;1HNMR(600MHz,CDCl3)δ8.25(d,J＝8.0Hz,1H),7.95(d,J＝7.8Hz,1H),7.88(d,J＝7.4Hz,1H),7.86–7.83(m,1H),7.75(dt,J＝14.5,7.6Hz,2H),7.70(d,J＝7.0Hz,1H),7.63(t,J＝7.4Hz,1H),7.48(s,1H);13C NMR(151MHz,CDCl3)δ178.75,157.50,149.28,147.69,147.62,134.43,133.36,133.00,132.03,130.99,130.52,129.72,128.61,124.84,124.38,120.69.HRMS(TOF):m/z[M+Na]+calculated for C16H9N3O6Na:362.0389;found:362.0394.
EXAMPLE 6 preparation of (2-methoxyphenyl) (5- (2-methoxyphenyl) oxazol-2-yl) methanone
Using 2-amino-1- (2-methoxyphenyl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as raw materials, the procedure of example 1 was followed to give a yellow solid in yield 49％.m.p.118-120℃;1H NMR(600MHz,CDCl3)δ7.95(d,J＝7.7Hz,1H),7.75(s,1H),7.67(d,J＝6.6Hz,1H),7.53(t,J＝7.9Hz,1H),7.38(t,J＝7.8Hz,1H),7.08(t,J＝7.5Hz,2H),7.02(dd,J＝13.2,8.4Hz,2H),3.99(s,3H),3.81(s,3H);13C NMR(151MHz,CDCl3)δ181.19,158.64,156.93,156.59,150.62,133.38,130.62,130.60,128.29,127.21,127.04,121.09,120.42,116.18,111.98,111.04,55.93,55.54.HRMS(TOF):m/z[M+Na]+calculated for C18H15NO4Na:332.0899;found:332.0902.
EXAMPLE 7 preparation of (2-fluorophenyl) (5- (2-fluorophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (2-fluorophenyl) ethanone hydrochloride, potassium iodide, t-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid in yield 80％.m.p.142-145℃;1H NMR(600MHz,CDCl3)δ7.98(td,J＝7.6,1.7Hz,1H),7.94(td,J＝7.5,1.8Hz,1H),7.74(d,J＝4.0Hz,1H),7.63-7.58(m,1H),7.45-7.40(m,1H),7.34-7.27(m,2H),7.26-7.18(m,2H);13C NMR(151MHz,CDCl3)δ177.82,161.97,160.45,158.77,156.66,149.12,134.61,131.59,131.41,128.48,128.39,127.31,125.06,124.95,124.15,116.76,116.62,116.25,116.11,115.28,115.20.HRMS(TOF):m/z[M+Na]+calculated for C16H9NO2F2Na:308.0499;found:308.0501.
Example 8 preparation of (3-nitrophenyl) (5- (3-nitrophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (3-nitrophenyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid .m.p.176-180℃;1HNMR(600MHz,CDCl3)δ9.48(s,1H),8.87(d,J＝7.4Hz,1H),8.68(s,1H),8.53(d,J＝7.7Hz,1H),8.32(d,J＝7.8Hz,1H),8.19(d,J＝7.3Hz,1H),7.84(s,1H),7.78(t,J＝7.8Hz,1H),7.73(t,J＝7.8Hz,1H);13C NMR(151MHz,CDCl3)δ175.88,156.84,152.38,148.87,148.34,136.26,136.06,130.93,130.55,129.83,128.21,128.04,126.04,125.86,124.68,120.36.HRMS(TOF):m/z[M+Na]+calculated for C16H9N3O6Na:362.0389;found:362.0393.
EXAMPLE 9 preparation of (3-chlorophenyl) (5- (3-chlorophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (3-chlorophenyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid .m.p.157-160℃;1HNMR(600MHz,CDCl3)δ8.51(t,J＝1.8Hz,1H),8.41(d,J＝7.8Hz,1H),7.82(s,1H),7.75-7.71(m,1H),7.66-7.63(m,2H),7.49(t,J＝7.9Hz,1H),7.44-7.41(m,2H);13C NMR(151MHz,CDCl3)δ177.01,156.87,153.05,136.61,135.38,134.80,133.81,130.76,130.49,130.12,129.79,128.95,128.23,125.44,124.75,123.51.HRMS(TOF):m/z[M+Na]+calculated for C16H9NO2Cl2Na:339.9908;found:339.9911.
EXAMPLE 10 preparation of (3-methoxyphenyl) (5- (3-methoxyphenyl) oxazol-2-yl) methanone
Using 2-amino-1- (3-methoxyphenyl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid .m.p.140-142℃;1HNMR(600MHz,CDCl3)δ8.14(d,J＝7.7Hz,1H),7.97(s,1H),7.60(s,1H),7.47-7.37(m,3H),7.34(s,1H),7.22-7.19(m,1H),6.98(d,J＝7.7Hz,1H),3.90(s,3H),3.89(s,3H);13C NMR(151MHz,CDCl3)δ178.36,160.18,159.66,157.05,154.08,136.57,130.24,129.46,127.95,124.17,123.63,120.49,117.93,116.00,114.85,110.57,55.50.HRMS(TOF):m/z[M+Na]+calculated for C18H15NO4Na:332.0899;found:332.0901.
EXAMPLE 11 preparation of 5-Methoxyoxazole-2-carboxylic acid methyl ester
Using glycine methyl ester hydrochloride, potassium iodide, t-butyl hydroperoxide and Ethyl Acetate (EA) as raw materials, the procedure of example 1 was followed to give a white solid .m.p.98-102℃;1HNMR(600MHz,CDCl3)δ6.36(s,1H),4.01(s,3H),3.96(s,3H);13C NMR(151MHz,CDCl3)δ161.97,155.64,143.03,102.08,58.90,52.80.HRMS(TOF):m/z[M+Na]+calculated for C6H7NO4Na:180.0273;found:180.0277.
EXAMPLE 12 preparation of furan-2 yl (5- (furan-2 yl) oxazol-2-yl) methanone
Using 2-amino-1- (furan-2-yl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a yellow solid .m.p.162-166℃;1HNMR(600MHz,DMSO-d6)δ8.23(s,1H),8.09(d,J＝2.9Hz,1H),7.98(s,1H),7.86(s,1H),7.15(s,1H),6.86(s,1H),6.76(s,1H).;13C NMR(151MHz,DMSO-d6)δ164.99,155.69,150.48,150.06,146.01,145.93,142.15,124.50,124.43,113.69,113.01,111.37.HRMS(TOF):m/z[M+Na]+calculated for C12H7NO4Na:252.0273;found:252.0277.
Example 13 preparation of (4-ethylphenyl) (5- (4-ethylphenyl) oxazol-2-yl) methanone
Using 2-amino-1- (4-ethylphenyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid .m.p.115-118℃;1HNMR(600MHz,CDCl3)δ8.41(d,J＝8.2Hz,2H),7.74(d,J＝8.1Hz,2H),7.55(s,1H),7.36(d,J＝8.1Hz,2H),7.31(d,J＝8.0Hz,2H),2.75(q,J＝7.6Hz,2H),2.71(q,J＝7.6Hz,2H),1.30(d,J＝7.8Hz,3H),1.27(d,J＝7.7Hz,3H);13C NMR(151MHz,CDCl3)δ178.38,157.05,154.36,150.85,146.54,133.20,130.99,128.61,128.00,125.47,124.30,123.30,29.08,28.81,15.24,15.08.HRMS(TOF):m/z[M+Na]+calculated for C20H19NO2Na:328.1313;found:328.1315.
EXAMPLE 14 preparation of (4-bromophenyl) (5- (4-bromophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (4-bromophenyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid in yield 83％.m.p.235-238℃;1H NMR(600MHz,CDCl3)δ8.40(d,J＝8.6Hz,2H),7.75-7.65(m,4H),7.63(s,1H),7.61(d,J＝4.3Hz,2H);13C NMR(151MHz,CDCl3)δ177.40,156.86,153.45,133.88,132.48,132.31,131.89,129.53,126.85,125.49,124.46,124.30.HRMS(TOF):m/z[M+Na]+calculated for C16H9NO2Br2Na:427.8898;found:427.8895.
EXAMPLE 15 preparation of (4-chlorophenyl) (5- (4-chlorophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (4-chlorophenyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid .m.p.188-191℃;1HNMR(600MHz,CDCl3)δ8.48(d,J＝8.7Hz,2H),7.76(d,J＝8.7Hz,2H),7.60(s,1H),7.51(d,J＝8.7Hz,2H),7.46(d,J＝8.7Hz,2H);13C NMR(151MHz,CDCl3)δ177.11,156.89,153.36,140.63,136.19,133.51,132.23,129.51,128.85,126.66,125.11,124.16.HRMS(TOF):m/z[M+Na]+calculated for C16H9NO2Cl2Na:339.9908;found:339.9909.
EXAMPLE 16 preparation of (4-methoxyphenyl) (5- (4-methoxyphenyl) oxazol-2-yl) methanone
Using 2-amino-1- (4-methoxyphenyl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as raw materials, the procedure of example 1 was followed to give a yellow solid in yield 81％.m.p.150-152℃;1H NMR(600MHz,CDCl3)δ8.53(d,J＝8.9Hz,2H),7.76(d,J＝8.7Hz,2H),7.47(s,1H),7.02-6.98(m,4H),3.91(s,3H),3.87(s,3H);13C NMR(151MHz,CDCl3)δ177.02,164.19,160.96,156.91,154.06,133.24,128.44,127.00,122.35,119.61,114.60,113.78,55.52,55.41.HRMS(TOF):m/z[M+Na]+calculated for C18H15NO4Na:332.0899;found:332.0902.
EXAMPLE 17 preparation of Parafresh (5- (p-tolyl) oxazol-2-yl) methanone
Using 2-amino-1- (p-tolyl) ethanone hydrochloride, potassium iodide, t-butylhydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a yellow solid .m.p.125-127℃;1HNMR(600MHz,CDCl3)δ8.39(d,J＝8.2Hz,2H),7.71(d,J＝8.2Hz,2H),7.54(s,1H),7.33(d,J＝8.0Hz,2H),7.33(d,J＝7.9Hz,2H),2.45(s,3H),2.41(s,3H);13C NMR(151MHz,CDCl3)δ178.33,157.00,154.32,144.73,140.24,132.96,130.89,129.79,129.18,125.36,124.08,123.25,21.76,21.44.HRMS(TOF):m/z[M+Na]+calculated for C18H15NO2Na:300.1000;found:300.1004.
EXAMPLE 18 preparation of (4-fluorophenyl) (5- (4-fluorophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (4-fluorophenyl) ethanone hydrochloride, potassium iodide, t-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid in yield 85％.m.p.153-157℃;1H NMR(600MHz,CDCl3)δ8.59(d,J＝5.7Hz,2H),7.82(d,J＝5.3Hz,2H),7.55(s,1H),7.19(dt,J＝16.5,8.5Hz,4H);13C NMR(151MHz,CDCl3)δ176.81,167.20,165.50,164.52,162.85,156.85,153.45,133.68,133.61,131.60,127.53,127.47,123.50,123.03,116.50,116.36,115.76,115.62.HRMS(TOF):m/z[M+Na]+calculated for C16H9NO2F2Na:308.0499;found:308.0504.
EXAMPLE 19 preparation of (3, 4-dimethoxyphenyl) (5- (3, 4-dimethoxyphenyl) oxazol-2-yl) methanone
Using 2-amino-1- (3, 4-dimethoxyphenyl) ethanone hydrochloride, potassium iodide, tert-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a yellow solid .m.p.195-196℃;1H NMR(600MHz,CDCl3)δ8.38(dd,J＝8.5,1.9Hz,1H),8.00(d,J＝1.9Hz,1H),7.49(s,1H),7.41(dd,J＝8.3,1.9Hz,1H),7.30(d,J＝1.9Hz,1H),6.97(dd,J＝16.3,8.5Hz,2H),3.99(s,3H),3.99(s,6H),3.95(s,3H);13C NMR(151MHz,CDCl3)δ176.92,156.91,154.16,150.69,149.59,148.97,128.43,126.39,122.64,119.80,118.76,112.68,111.59,110.24,108.41,56.12,56.03.HRMS(TOF):m/z[M+Na]+calculated for C20H19NO6Na:392.1110;found:392.1110.
EXAMPLE 20 preparation of (3, 4-difluorophenyl) (5- (3, 4-difluorophenyl) oxazol-2-yl) methanone
Using 2-amino-1- (3, 4-difluorophenyl) ethanone hydrochloride, potassium iodide, t-butyl hydroperoxide and Ethyl Acetate (EA) as starting materials, the procedure of example 1 was followed to give a white solid .m.p.150-152℃;1HNMR(600MHz,CDCl3)δ8.50-8.45(m,1H),8.41(dt,J＝4.2,2.1Hz,1H),7.67-7.62(m,1H),7.58(d,J＝5.6Hz,2H),7.31(td,J＝17.7,8.6Hz,2H);13C NMR(151MHz,CDCl3)δ175.46,156.67,155.25,153.53,152.49,152.33,151.73,151.06,150.64,150.07,149.40,131.85,128.22,128.20,124.29,122.01,121.98,120.39,120.28,118.53,118.41,117.57,117.45,114.83,114.70.HRMS(TOF):m/z[M+Na]+calculated for C16H7NO2F4Na:344.0311;found:344.0315.
EXAMPLE 21 preparation of phenyl (5-phenyloxazol-2-yl) methanone
To a 50mL eggplant-shaped bottle were added 2-aminoacetophenone hydrochloride (0.17 g,1.0 mmol), potassium iodide (0.32 g,2.0 mmol), tert-butyl hydroperoxide (0.76 g,6.0 mmol) and Ethyl Acetate (EA) 10mL, and the reaction was stirred at room temperature for about 6 hours. After completion of the reaction by thin layer chromatography, 10mL of a saturated sodium thiosulfate solution, 40mL of water and 50mL of ethyl acetate were added for extraction, and the organic layer was dried over anhydrous sodium sulfate and concentrated. And (3) drying the solid, and purifying by column chromatography to obtain a yellow solid.
EXAMPLE 22 preparation of phenyl (5-phenyloxazol-2-yl) methanone
To a 50mL eggplant-shaped bottle were added 2-aminoacetophenone hydrochloride (0.17 g,1.0 mmol), potassium iodide (0.48 g,3.0 mmol), tert-butyl hydroperoxide (0.76 g,6.0 mmol) and Ethyl Acetate (EA) 10mL, and the reaction was stirred at room temperature for about 8 hours. After completion of the reaction by thin layer chromatography, 10mL of a saturated sodium thiosulfate solution, 40mL of water and 50mL of ethyl acetate were added for extraction, and the organic layer was dried over anhydrous sodium sulfate and concentrated. And (3) drying the solid, and purifying by column chromatography to obtain a yellow solid.
Claims (5)
1. The preparation method of the 2-aroyl substituted oxazole compound comprises the steps of taking hydrochloride of a 2-amino substituted aryl ethanone compound shown in a formula (I) as a raw material, taking tert-butyl hydroperoxide and potassium iodide as catalysts, taking ethyl acetate as a solvent, reacting for 6 hours at room temperature, and obtaining the 2-ketone-1, 3-oxazole compound shown in a formula (II), wherein the reaction equation is as follows:
wherein R is selected from phenyl, p-nitrophenyl, p-methoxyphenyl, p-fluorophenyl and p-methylphenyl.
2. The preparation method according to claim 1, wherein the molar ratio of the tert-butyl hydroperoxide to the potassium iodide is 2:1-3:1.
3. The process according to claim 1, wherein the molar ratio of t-butyl hydroperoxide to potassium iodide is 3:1.
4. The process according to claim 1, wherein the molar ratio of the compound of formula (I) to potassium iodide is from 1:1 to 1:3.
5. The process according to claim 1, wherein the molar ratio of the compound of formula (I) to potassium iodide is 1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211452437.XA CN115819366B (en) | 2022-11-21 | 2022-11-21 | Preparation method of 2-aroyl substituted oxazole compound and compound prepared by same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211452437.XA CN115819366B (en) | 2022-11-21 | 2022-11-21 | Preparation method of 2-aroyl substituted oxazole compound and compound prepared by same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115819366A CN115819366A (en) | 2023-03-21 |
| CN115819366B true CN115819366B (en) | 2024-05-24 |
Family
ID=85529475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211452437.XA Active CN115819366B (en) | 2022-11-21 | 2022-11-21 | Preparation method of 2-aroyl substituted oxazole compound and compound prepared by same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115819366B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004065374A1 (en) * | 2003-01-17 | 2004-08-05 | Astellas Pharma Inc. | Oxazole derivatives as inhibitors of cyclooxygenase |
| CN111995620A (en) * | 2020-07-02 | 2020-11-27 | 重庆医科大学 | Preparation method of 1,3, 4-thiadiazole compound and compound prepared by same |
| CN113717121A (en) * | 2021-09-30 | 2021-11-30 | 南开大学 | Preparation method of 5-fluoroalkyl substituted oxazole compound |
-
2022
- 2022-11-21 CN CN202211452437.XA patent/CN115819366B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004065374A1 (en) * | 2003-01-17 | 2004-08-05 | Astellas Pharma Inc. | Oxazole derivatives as inhibitors of cyclooxygenase |
| CN111995620A (en) * | 2020-07-02 | 2020-11-27 | 重庆医科大学 | Preparation method of 1,3, 4-thiadiazole compound and compound prepared by same |
| CN113717121A (en) * | 2021-09-30 | 2021-11-30 | 南开大学 | Preparation method of 5-fluoroalkyl substituted oxazole compound |
Non-Patent Citations (3)
| Title |
|---|
| Formation of 2-Acyloxazoles by a Multipathway Coupled Domino Strategy: One-Pot Metal-Free Oxidative Cyclization Applicable to Various Substrates;Xue, Wei-Jian, et al;《Asian Journal of Organic Chemistry》;第2卷(第8期);第638-641页 * |
| Wang, Can,et al.Employing Thiocyanate Salts as Nitrogen Source via C=N Bond Cleavage: Divergent Synthesis of α-Ketoamides and 2-Acyloxazoles.《Organic Chemistry Frontiers》.2019,第6卷第2534-2538页. * |
| Zhang, Ruiqiang,et al.Synthesis and structure-activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization.《Bioorganic & Medicinal Chemistry Letters》.2021,第40卷第1-5页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115819366A (en) | 2023-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101429165A (en) | Synthesis of quinazoline ketone compounds | |
| CN105198888A (en) | 2,3a-disubstituted-3H-pyrazole[1,5-a]indole-4(3aH)-ketone, derivative and synthetic method of 2,3a-disubstituted-3H-pyrazole[1,5-a]indole-4(3aH)-ketone and derivative | |
| CN115819366B (en) | Preparation method of 2-aroyl substituted oxazole compound and compound prepared by same | |
| CN111362895A (en) | Synthesis method of naphthofuran derivative, naphthofuran derivative and application | |
| CN105061348B (en) | A kind of preparation method of 2 substituted benzene Bing oxazole compounds | |
| CN104447604A (en) | Synthetic method for chiral quaternary carbon oxazolidinone compound | |
| CN107082771A (en) | Double α cyano group imines substituted isochroman class compounds and its synthetic method | |
| CN104592104B (en) | Method for preparing 2-chloronicotinic acid | |
| CN111777564B (en) | Method for synthesizing quinazolinone compound by photocatalytic alcohol oxidation in aqueous phase | |
| CN107501204B (en) | Method for synthesizing 1, 3-substituted thiazole ring compound from styrene compound | |
| Zhang et al. | Cu (i)-Catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1, 3-O-transposition reaction | |
| CN109705050B (en) | Method for synthesizing 4-sulfenyl isoxazole | |
| Grigg et al. | Dihydrofurocoumarin and dihydrofurodihydropyrid-2-one derivatives via palladium catalysed cascades involving aryl/heteroaryl/vinyl iodides and allene followed by acid catalysed cyclisation | |
| Li et al. | Highly Enantioselective Synthesis of α‐Trifluoromethyldihydropyrans Using a Chiral Trifluoroethyl‐substituted Thiourea Catalyst Derived from Amino Acid | |
| Shaabani et al. | Guanidinium-based sulfonic acid: an efficient Brønsted acid organocatalyst for the synthesis of fused polycyclic dihydropyridines in water | |
| CN109456243A (en) | One kind (Z)-β-selenium cyanic acid ester group acrylate compounds and preparation method thereof | |
| CN105061257A (en) | Method for selectively reducing 4-nitrophenylacetonitrile/aldehyde condensation reaction product | |
| CN112645896B (en) | Method for synthesizing 4-aryl isoxazole derivative | |
| CN112939883B (en) | Preparation method of polysubstituted 1, 3-oxazolidine compound | |
| CN105237466B (en) | A kind of method for synthesizing three substituted pyridine derivatives | |
| Ren et al. | One-pot method for stereoselective cyclopropanation of electron-deficient olefins with methyl bromoacetate and phenacyl bromide in the presence of triphenylarsine | |
| CN104327025B (en) | A kind of preparation method of 4-arylnaphthalene lactone derivative | |
| CN112939903A (en) | Method for preparing furan compound from aryl ketone bromide | |
| CN100339360C (en) | Process for producing aromatic nitrile compound | |
| CN110256451A (en) | A kind of synthetic method of benzofuran simultaneously [2,3-b] quinoline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |