CN108947995B - Preparation method of polysubstituted oxadiazine derivative - Google Patents
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- 150000005063 oxadiazines Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- VOHWEKIUKSUIDT-UHFFFAOYSA-N 2-iodoethynylbenzene Chemical class IC#CC1=CC=CC=C1 VOHWEKIUKSUIDT-UHFFFAOYSA-N 0.000 claims abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims description 6
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical class ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 238000001311 chemical methods and process Methods 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
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 4
- 238000001308 synthesis method Methods 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000741 silica gel Substances 0.000 abstract description 2
- 229910002027 silica gel Inorganic materials 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 40
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- -1 1,2, 4-oxadiazine compound Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 238000003541 multi-stage reaction Methods 0.000 description 2
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 1
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 1
- 239000003513 alkali Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000144 sodium(I) superoxide Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a preparation method of a polysubstituted oxadiazine derivative, belonging to the technical field of organic synthesis. The method comprises the following steps: and (2) adding substituted benzylaminoxime, substituted phenylethynyl iodonium salt and potassium hydroxide into a reaction container in sequence, adding a solvent tetrahydrofuran, stirring at room temperature until the reaction is finished for 4 hours, concentrating the filtrate by using a rotary evaporator to obtain a crude product, and performing chromatographic separation on the crude product by using a silica gel column to obtain the target compound. The synthesis method of the oxadiazine derivative provided by the invention has the characteristics of being scientific and reasonable, simple, mild in reaction condition, easy to purify the product and the like. The reaction equation is as follows:
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a polysubstituted oxadiazine derivative.
Background
Oxadiazines are one of the less sought after heterocyclic compounds containing N, O and are present in natural products as well as in biologically active molecules. It is used as gamma-secretase regulator and can be used for treating Alzheimer disease. ((a) J.org.chem.2017,82,2957-2964.(b) J.Med.chem.2001,44,619.)
Meanwhile, the document reports that the oxadiazine derivative has important functions in the aspects of pesticides and plant growth regulation. (Chemistry Of Heterocyclic Compounds.2017,53(5), 495-
In view of the wide biological activity and application value of the oxadiazine derivative, the development of a novel method for practically and effectively synthesizing the polysubstituted oxadiazine derivative is of great significance.
In recent years, the preparation of polysubstituted oxadiazine derivatives has been carried out by:
1) in 2006, the Cho subject group developed a 1,2, 4-oxadiazine compound which is synthesized by two steps starting from oxime and taking scandium trifluoromethanesulfonate as a catalyst. (Tetrahedron letters.2006,47, 9029-
2) In 2017, an oxadiazine derivative is developed by a Matthew G.Burscavich subject group through multi-step reaction starting from amide. (J.Med.chem.2017,60,2383-
The above-mentioned process for the preparation of polysubstituted oxadiazine derivatives has certain drawbacks: 1) a multi-step reaction is required, and the final yield is low; 2) some metal catalysts are used; 3) the reaction time is long.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of a polysubstituted oxadiazine derivative as a supplement to a synthesis method of a conventional oxadiazine derivative.
A process for the preparation of a polysubstituted oxadiazine derivative having the structure shown in formula i:
R1the substituent group is selected from fluorine, chlorine, bromine, iodine, ester group and phenyl; r2The substituent group is selected from fluorine, chlorine and bromine; the method is characterized in that substituted benzamidoxime, substituted phenylethynyl iodonium salt and alkali are added into a reactor, after the reaction in a solvent is completed by stirring, a rotary evaporator is used for concentrating to obtain a crude product, the crude product is separated by silica gel column chromatography to obtain a target product, and the chemical process is shown in a reaction formula II:
the molar ratio of the substituted benzamidoxime to the substituted phenylethynyl periodate to the potassium hydroxide is 1:1.2: 1.5. The solvent is tetrahydrofuran, the reaction temperature is room temperature, and the reaction time is 4 h.
The invention has the beneficial effects that: the synthesis method of the polysubstituted oxadiazine derivative provided by the invention is scientific and reasonable, provides a new way, and obtains products with various substituent groups through the method, and is characterized in that: easy obtaining of raw materials, simple operation, mild reaction conditions, short reaction time and the like.
Drawings
FIG. 1 is an NMR spectrum of compound 3aa prepared in example 1;
FIG. 2 is an NMR spectrum of compound 3da prepared in example 4;
FIG. 3 is an NMR spectrum of Compound 3ac prepared in example 7.
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
the test methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
1) Preparation of oxadiazine derivative 3aa
A10 mL round-bottom flask was charged with benzamidoxime 1a (0.3mmol,40.8mg), 2a (0.36mmol,125.3mg) and KOH (0.45mmol,25.2 mg). Tetrahydrofuran (3mL) was added, and the mixture was stirred at room temperature to react for 4 hours. After the reaction was completed, the solvent was removed by using a rotary evaporator to obtain a crude product, which was separated by column chromatography (200-mesh 300-mesh silica gel) (petroleum ether/ethyl acetate: 3/1), and the solvent was removed by using a rotary evaporator to obtain the target product 3aa with a yield of 77%.
Spectrum analysis data 3aa:
1H NMR(500MHz,DMSO-d6)δ8.00(s,1H),7.86(d,1H),7.81(d,J＝6.4Hz,2H),7.75(d,J＝6.9Hz,2H),7.56–7.43(m,5H),7.39(d,J＝7.2Hz,2H),7.30–7.20(m,4H),7.18–7.09(m,3H),6.97(d,J＝7.2Hz,2H),4.42–4.32(m,1H),3.58(d,J＝12.9Hz,1H).13C NMR(125MHz,DMSO-d6)δ152.97,142.25,135.11,134.18,133.34,132.02,130.95,130.15,129.00,128.57,128.24,128.01,127.48,127.09,126.84,125.83,124.57,116.24,101.13,44.41.HRMS(ESI)m/z calcd for C30H25N4O2 +(M+H)+473.1978,found 473.1974.
example 2
1a in example 1 is replaced by 1b, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3ba:
1H NMR(500MHz,DMSO-d6)δ8.03(d,J＝5.1Hz,1H),7.84(dd,J＝8.5,5.5Hz,2H),7.76–7.71(m,3H),7.50(dd,J＝8.5,5.7Hz,2H),7.36(dt,J＝19.5,8.2Hz,4H),7.25–7.15(m,4H),7.05(dt,J＝12.6,8.3Hz,4H),4.40(dd,J＝13.1,5.8Hz,1H),3.58(d,J＝13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ152.07,135.10,134.10,130.32,129.66,129.17,129.12,129.02,128.38,128.12,125.88,125.59,124.59,116.03(d,J＝15.5Hz),115.80,115.23(d,J＝21.0Hz),44.16.HRMS(ESI)m/z calcd for C30H23F2N4O2 +(M+H)+509.1789,found 509.1789.
example 3
1a in example 1 is replaced by 1c, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3ca:
1H NMR(500MHz,DMSO-d6)δ8.05(d,J＝4.9Hz,1H),7.77(d,J＝8.4Hz,2H),7.71(d,J＝7.7Hz,2H),7.67(s,1H),7.58–7.49(m,4H),7.37(t,J＝7.6Hz,2H),7.28(d,J＝8.4Hz,2H),7.23(t,J＝7.3Hz,4H),7.07(t,J＝7.7Hz,2H),4.41(dd,1H),3.57(d,J＝13.1Hz,1H).13C NMR(125MHz,DMSO-d6)δ151.86,141.34,135.64,135.32,133.98,133.65,133.16,130.66,130.41,129.01,128.45,128.37,128.20,127.79,127.22,125.94,124.60,116.24,101.51,44.08.HRMS(ESI)m/z calcd for C30H23Cl2N4O2 +(M+H)+541.1198,found 541.1196.
example 4
1a in example 1 is replaced by 1d, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3da:
1H NMR(500MHz,DMSO-d6)δ8.09(d,J＝5.3Hz,1H),7.74–7.68(m,6H),7.66(s,1H),7.47(d,J＝8.6Hz,2H),7.43(d,J＝8.6Hz,2H),7.38(t,J＝7.7Hz,2H),7.27–7.22(m,4H),7.09(t,J＝7.8Hz,2H),4.43(dd,J＝13.2,5.9Hz,1H),3.58(d,J＝13.1Hz,1H).13C NMR(125MHz,DMSO-d6)δ151.92,141.42,135.38,133.87(d,J＝27.6Hz),131.86,131.15(d,J＝32.3Hz),130.42,129.13(d,J＝29.9Hz),128.42(d,J＝52.4Hz),127.22,125.96,124.51(d,J＝23.2Hz),121.87,116.22,101.58,44.11.HRMS(ESI)m/z calcd for C30H23Br2N4O2 +(M+H)+629.0188,found 629.0182.
example 5
1a in example 1 is replaced by 1e, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3ea:
1H NMR(500MHz,DMSO-d6)δ8.04(d,J＝5.1Hz,1H),7.86(d,J＝8.5Hz,2H),7.73–7.68(m,2H),7.64–7.58(m,3H),7.52(d,J＝8.5Hz,2H),7.40–7.32(m,4H),7.29–7.22(m,4H),7.13–7.07(m,2H),4.41(dd,J＝13.3,5.9Hz,1H),3.56(d,J＝12.7Hz,1H).13C NMR(125MHz,DMSO-d6)δ152.14,141.66,137.76,137.19,135.41,134.03,133.90,131.39,130.47,129.27,129.07,128.57,128.52,128.29,127.28,126.03,124.65,116.26,101.65,98.12,95.09,44.17.HRMS(ESI)m/z calcd for C30H23F2N4O2 +(M+H)+724.9910,found 724.9909.
example 6
2a in example 1 is replaced by 2b, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrum analysis data 3ab:
1H NMR(500MHz,DMSO-d6)δ8.03(d,J＝5.3Hz,1H),7.87(s,1H),7.86–7.79(m,4H),7.56–7.49(m,3H),7.44(dd,J＝6.5,2.9Hz,2H),7.31–7.27(m,3H),7.21(t,J＝8.8Hz,2H),7.12(dd,J＝8.7,5.4Hz,2H),6.75(t,J＝8.8Hz,2H),4.42(dd,J＝13.1,5.9Hz,1H),3.60(d,J＝13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ163.10(d,J＝246.5Hz),161.59(d,J＝242.4Hz),153.03,142.30,134.36,131.98,130.99,130.72,129.50,128.97,128.84,128.69,128.22,127.43,126.91,126.56,116.25,115.82(d,J＝21.3Hz),114.81(d,J＝21.5Hz),100.75,44.05.HRMS(ESI)m/z calcd for C30H23F2N4O2 +(M+H)+509.1789,found 509.1784.
example 7
2a in example 1 was replaced by 2c, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Spectrogram analysis data 3ac:
1H NMR(500MHz,DMSO-d6)δ8.04(d,J＝5.3Hz,1H),7.92(s,1H),7.85–7.78(m,4H),7.56–7.49(m,3H),7.45–7.37(m,4H),7.29(t,J＝6.2Hz,3H),7.05(d,J＝8.6Hz,2H),6.95(d,J＝8.5Hz,2H),4.40(dd,J＝13.1,5.8Hz,1H),3.58(d,J＝13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ153.13,142.52,135.17,134.08,133.05,131.98,131.41,131.02,128.98,128.80,128.73,128.18,127.94,127.69,127.51,126.94,126.36,116.88,100.83,43.87.HRMS(ESI)m/z calcd for C30H23Cl2N4O2 +(M+H)+541.1198,found 541.1196.
example 8
2a in example 1 is replaced by 2d, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3ad:
1H NMR(500MHz,DMSO-d6)δ8.05(d,J＝5.3Hz,1H),7.93(s,1H),7.85–7.81(m,2H),7.74(d,J＝8.4Hz,2H),7.53(ddd,J＝19.6,10.5,5.2Hz,5H),7.41–7.37(m,2H),7.30(q,J＝6.8,6.1Hz,3H),4.39(dd,J＝13.1,5.8Hz,1H),3.59(d,J＝13.1Hz,1H).13C NMR(125MHz,DMSO-d6)δ153.15,142.58,134.13,133.44,132.44,131.95,131.88,131.00,130.88,128.96,128.80,128.76,128.17,127.90,127.54,126.92,126.70,124.03,119.88,116.89,100.96,43.87.HRMS(ESI)m/z calcd for C30H23Br2N4O2 +(M+H)+629.0188,found 629.0181.
example 9
1f is used instead of 1a in example 6, the conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3fb:
1H NMR(500MHz,DMSO-d6)δ8.21(d,J＝5.3Hz,1H),8.01(d,J＝8.3Hz,2H),7.87(d,J＝8.3Hz,2H),7.84–7.75(m,4H),7.70–7.64(m,3H),7.29(dd,J＝8.5,5.5Hz,2H),7.20(t,J＝8.8Hz,2H),6.87(t,J＝8.7Hz,2H),4.49(dd,J＝13.2,5.8Hz,1H),3.88(s,3H),3.83(s,3H),3.57(d,J＝13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ166.14,163.27(d,J＝247.9Hz),161.74(d,J＝243.5Hz),151.83,141.42,135.97,135.04,132.97,131.54,130.39,129.99,129.52,129.17(d,J＝21.0Hz),128.55,128.48,127.29,126.94,126.72,126.65,116.55,115.84(d,J＝21.4Hz),115.18(d,J＝21.8Hz),101.45,52.73,52.47,43.86.HRMS(ESI)m/z calcd for C34H26F2N4NaO2 +(M+Na)+647.1718,found 647.1716.
example 10
1a in example 6 was replaced with 1g, and the experimental results were shown in Table 1, under the same conditions as in example 1.
Spectrogram analysis data 3gb:
1H NMR(500MHz,DMSO-d6)δ8.12(d,J＝5.8Hz,1H),7.91(d,J＝8.0Hz,2H),7.85–7.77(m,5H),7.69(dd,J＝21.6,7.6Hz,4H),7.60(t,J＝6.0Hz,4H),7.49(q,J＝8.1Hz,4H),7.40(dt,J＝14.1,7.3Hz,2H),7.29–7.21(m,4H),6.81(t,J＝8.6Hz,2H),4.48(dd,J＝13.2,5.8Hz,1H),3.64(d,J＝12.9Hz,1H).13C NMR(125MHz,DMSO-d6)δ163.17(d,J＝247.2Hz),161.63(d,J＝243.3Hz),152.57,142.52,142.15,140.28,140.02,139.65,134.51,130.86,130.72,129.91,129.41,128.45,128.35,128.04,127.95,127.35,127.18,127.09,127.00,126.60,126.51,116.23,115.84(d,J＝21.4Hz),114.94(d,J＝21.5Hz),101.09,44.08.HRMS(ESI)m/z calcd for C42H31F2N4O2 +(M+H)+661.2415,found 661.2425.
TABLE 1
Claims (2)
1. A process for the preparation of a polysubstituted oxadiazine derivative having the structure shown in formula i:
R1the substituent group is selected from fluorine, chlorine, bromine, iodine, carbomethoxy and phenyl; r2The substituent group is selected from fluorine, chlorine and bromine; it is characterized in that substituted benzamidoxime, substituted phenylethynyl iodonium salt and KOH are added into a reactor and stirred in tetrahydrofuran at room temperatureStirring for 4 hours, after the reaction is finished, concentrating by using a rotary evaporator to obtain a crude product, and separating the crude product by using silica gel column chromatography to obtain a compound shown as a formula I, wherein the chemical process is shown as a reaction formula II:
2. the method of claim 1, wherein: the molar ratio of the substituted benzamidoxime to the substituted phenylethynyl iodonium salt to the potassium hydroxide is 1:1.2: 1.5.
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|---|---|---|---|---|
| CN104327008A (en) * | 2014-10-30 | 2015-02-04 | 湖南大学 | Synthesis method of benzoxazole compound |
| CN107629020A (en) * | 2017-09-28 | 2018-01-26 | 湖北科技学院 | A kind of (6H) ketone compounds of 1,2,4 oxadiazines of 4H 5 and its synthetic method |
| CN108314658A (en) * | 2018-04-12 | 2018-07-24 | 青岛科技大学 | A kind of preparation method of Duo substituted oxazoles derivative |
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2018
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104327008A (en) * | 2014-10-30 | 2015-02-04 | 湖南大学 | Synthesis method of benzoxazole compound |
| CN107629020A (en) * | 2017-09-28 | 2018-01-26 | 湖北科技学院 | A kind of (6H) ketone compounds of 1,2,4 oxadiazines of 4H 5 and its synthetic method |
| CN108314658A (en) * | 2018-04-12 | 2018-07-24 | 青岛科技大学 | A kind of preparation method of Duo substituted oxazoles derivative |
Non-Patent Citations (1)
| Title |
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| One Base for Two Shots: Metal-Free Substituent-Controlled Synthesis of Two Kinds of Oxadiazine Derivatives from Alkynylbenziodoxolones and Amidoximes;Ming Li，等;《The Journal of Organic Chemistry》;20190514;第84卷;第6904-6915页 * |
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