CN105541767B - A kind of method that different Aurone compound is prepared through Intra-molecular condensation - Google Patents
A kind of method that different Aurone compound is prepared through Intra-molecular condensation Download PDFInfo
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- -1 Aurone compound Chemical class 0.000 title claims abstract description 15
- 229930015036 aurone Natural products 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000009833 condensation Methods 0.000 title claims abstract description 7
- 230000005494 condensation Effects 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- 239000002904 solvent Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 230000035484 reaction time Effects 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 230000000694 effects Effects 0.000 claims abstract description 5
- 239000002585 base Substances 0.000 claims description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 7
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 6
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 6
- 229960004643 cupric oxide Drugs 0.000 claims description 5
- 229940112669 cuprous oxide Drugs 0.000 claims description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 4
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 229940116318 copper carbonate Drugs 0.000 claims description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical group [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 3
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000001119 stannous chloride Substances 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 3
- 235000019798 tripotassium phosphate Nutrition 0.000 claims description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229960003540 oxyquinoline Drugs 0.000 claims description 2
- 229940113115 polyethylene glycol 200 Drugs 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims 1
- 238000012805 post-processing Methods 0.000 abstract description 2
- 125000003118 aryl group Chemical group 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 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- 239000010410 layer Substances 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001530 aurones Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical class C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical class CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical group OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000003915 DNA Topoisomerases Human genes 0.000 description 1
- 108090000323 DNA Topoisomerases Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000006617 Intramolecular Heck reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical compound [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052927 chalcanthite Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229930184986 isoaurone Natural products 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses a kind of method that different Aurone compound is prepared through Intra-molecular condensation, it is using the aromatic substituted acrylic acid class compounds of E 2 (2 bromo aryl) 3 as raw material, under catalyst and part effect, under the conditions of the presence of alkali and microwave reaction, a period of time is reacted in solvent；After the completion of reaction, reaction solution is poured into water, is acidified to pH=3~4, is extracted, dries, is spin-dried for solvent, purifies, obtains different Aurone compound.This method has the advantages that raw material is simple and easy to get, the reaction time is short, post processing is simple, yield is higher.
Description
Technical field
The present invention relates to organic synthesis field, more particularly to one kind prepares different Aurone compound through Intra-molecular condensation
Method.
Background technology
Different aurones (Isoaurones), entitled (3H) -one of 3- benzene methene base benzofuran -2 of chemistry, is a kind of rare class
Flavonoids natural products, there are multiple biological activities, such as anti-tobacco virus, anticancer, anti-oxidant, topoisomerase I inhibitory activity
Deng (J.Pharmacol.Sci.2014,125,193), in the treatment of the diseases such as dysentery, toothache, fever, urinary tract and skin infection
In also there is potential application prospect (Tetrahedron Lett.2000,41,1579).Content of the different aurones in nature
Very rare (Bioorg.＆Med.Chem.Lett.2005,15,4313), limit and it is further studied and using opening
Hair.The synthetic method for the different Aurone compound reported at present mainly includes following two class：First, o-hydroxy phenylacetic acid or benzo furan
Mutter -2- ketone and substituted benzaldehyde under lewis acid or highly basic effect condensation reaction (Bioorg.Med.Chem.Lett.2005,
15,2065；Tetrahedron 2006,62,9855)；Second, esterification and intramolecular Heck of the adjacent iodo phenol under palladium chtalyst are anti-
Answer (Bioorg.Med.Chem.Lett.2005,15,4313).But both approaches are all present that the reaction time is longer, yield
The shortcomings of relatively low and use precious metal catalyst.
The content of the invention
It is an object of the invention to overcome shortcoming present in prior art, there is provided a kind of reaction time is short, yield is higher
The method that different Aurone compound is prepared through Intra-molecular condensation.
The purpose of the present invention is achieved through the following technical solutions：
A kind of method that different Aurone compound is prepared through Intra-molecular condensation, it is with E-2- (2- bromo aryls) -3-
Aromatic substituted acrylic acid class compound (structural formula 1) is raw material, under catalyst and part effect, presence and microwave reaction bar in alkali
Under part, a period of time is reacted in solvent；After the completion of reaction, reaction solution is poured into water, is acidified to pH=3~4, is extracted, is done
It is dry, solvent is spin-dried for, purifies, obtains different Aurone compound (structural formula 2).
Chemical equation of the present invention is as follows：
In formula 1, formula 2, the substituent R of A rings1It is single or multiple H, OH, OCH that can be, but not limited to3；The substituent R of B rings2
It is single or multiple F, Cl, Br, OCH that can be, but not limited to3、OH、CF3、NO2。
Described catalyst can be, but not limited to be copper acetate (Cu (OAc)2), cupric oxide (CuO), basic copper carbonate (Cu2
(OH)2CO3), Kocide SD (Cu (OH)2), copper sulphate (CuSO4), cupric sulfate pentahydrate (CuSO4·5H2O), cuprous oxide
(Cu2O), cuprous iodide (CuI), stannous chloride (CuCl), cuprous bromide (CuBr), thiophene -2-carboxylic acid are cuprous (CuTc), preferably
Catalyst is cuprous oxide.
Described part can be, but not limited to be DMAP (DMAP), tetramethylethylenediamine (TMEDA), 8- hydroxyls
Base quinoline (Oxine), 1,10- neighbours phenanthroline (1,10-phen), glycine (Glycine), preferably part are 1,10- neighbour's coffee hello
Quinoline.
Described alkali can be, but not limited to be triethylene diamine (DABCO), tripotassium phosphate (K3PO4), sodium carbonate
(Na2CO3), sodium acid carbonate (NaHCO3), sodium acetate (NaOAc), caustic alcohol (C2H5Ona), pyridine (Pyridine), triethylamine
(Et3N) etc., preferably alkali is triethylamine.
Described solvent can be, but not limited to be dimethyl sulfoxide (DMSO) (DMSO), N,N-dimethylformamide (DMF), poly- second two
Alcohol -200 (PEG-400), PEG-4000 (PEG-400), preferred solvent is PEG-4000.
Described E-2- (2- bromo aryls) -3- aromatic substituted acrylic acid classes compound, catalyst, part, alkali material amount
The ratio between be 1:(0.05~0.3)：(0.05~0.3)：(1~3), preferably E-2- (2- bromo aryls) -3- aromatic substituted acrylic acid classes
Compound, catalyst, part, the ratio between the amount of material of alkali are 1:0.2：0.2：2.
Described reaction temperature is 130~150 DEG C, and preferable reaction temperature is 140 DEG C.
The described reaction time is 2~30 minutes, and preferred reaction time is 2~20 minutes.
The present invention has the following advantages that compared with prior art and effect：
(1) raw material of the invention is easy to get, and raw material E-2- (2- bromo aryls) -3- aromatic substituted acrylic acid class compounds can pass through 2-
The fragrant acetic acid of bromine substitution is prepared with the aromatic formaldehyde substituted through Perkin condensation reactions.
(2) quick and high efficient reaction of the invention, by the way of microwave heating, can be reacted completely within 2-30 minutes, and
And post processing is easy, reaction solution is acidified, extracts, and dries, and column chromatography can purify.
(3) yield of the invention is higher, can reach 89%.
Embodiment
Further detailed description is done to the present invention with reference to embodiment, but the implementation of the present invention is not limited to this.
Embodiment 1:The synthesis of E-3- (3,4- dimethoxy benzene methenes base) -6- hydroxyl benzofurans -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (3,4- Dimethoxyphenyl) is sequentially added
Acrylic acid (3mmol, 1.1370g), cuprous oxide (0.6mmol, 0.0859g), 1,10-phen (0.6mmol, 0.1189g),
Et3N (6mmol, 0.6072g), 20mL PEG-400, stir, under microwave condition, 140 DEG C of controlling reaction temperature, react 20 points
Clock.After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times, be associated with 30mL ethyl acetate
Machine layer, organic layer are dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Faint yellow solid 0.7965g is obtained, is E-3-
(3,4- dimethoxy benzene methene base) -6- hydroxyl benzofurans -2 (3H) -one, yield 89%.
1H NMR(400MHz,DMSO-d6) δ 10.35 (s, 1H), 7.74 (d, J=8.4Hz, 1H), 7.55 (s, 1H), 7.41
(dd, J=1.6,8.0Hz, 1H), 7.36 (d, J=1.6Hz, 1H), 7.13 (d, J=8.4Hz, 1H), 6.67 (d, J=2.0Hz,
1H), 6.60 (dd, J=2.0,8.4Hz, 1H), 3.85 (s, 3H), 3.81 (s, 3H)；13C NMR(100MHz,DMSO-d6)δ
169.0,159.9,154.9,150.5,148.4,136.6,126.3,123.4,123.3,118.7,112.7,112.6,
111.5,111.0,98.4,55.5,55.4。
Embodiment 2：The synthesis of E-3- (3,5- dimethoxy benzene methenes base) benzofuran -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (2- bromophenyls) -3- (3,5- Dimethoxyphenyl) acrylic acid is sequentially added
(3mmol, 1.0896g), cuprous oxide (0.3mmol, 0.0430g), 1,10-phen (0.3mmol, 0.0595g), Et3N
(3mmol, 0.3036g), 20mL PEG-400, stir, under microwave condition, 130 DEG C of controlling reaction temperature, react 30 minutes.Instead
After the completion of answering, pour into 200mL water, pH=4 be acidified to watery hydrochloric acid, extracted 3 times with 30mL ethyl acetate, merge organic layer,
Organic layer is dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.3811g is obtained, is E-3- (3,5- bis-
Methoxybenzene methene base) benzofuran -2 (3H) -one, yield 45%.
1H NMR(400MHz,DMSO-d6) δ 7.81 (s, 1H), 7.78 (d, J=7.6Hz, 1H), 7.45 (t, J=7.6Hz,
1H), 7.31 (d, J=8.0Hz, 1H), 7.19 (t, J=7.6Hz, 1H), 6.95 (d, J=2.0Hz, 2H), 6.68 (t, J=
2.0Hz,1H),3.80(s,6H)；13C NMR(100MHz,DMSO-d6)δ168.0,160.6,153.8,140.8,135.2,
131.3,124.0,122.8,121.7,121.2,111.2,107.2,102.8,55.4。
Embodiment 3：The synthesis of E-3- (3,5- dimethoxy benzene methenes base) -6- hydroxyl benzofurans -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (3,5- Dimethoxyphenyl) is sequentially added
Acrylic acid (3mmol, 1.1370g), copper sulphate (0.9mmol, 0.1437g), DMAP (0.9mmol, 0.1100g), DABCO
(9mmol, 1.0096g), 20mL PEG-400, stir, under microwave condition, 150 DEG C of controlling reaction temperature, react 2 minutes.Reaction
After the completion of, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times with 30mL ethyl acetate, merge organic layer, have
Machine layer is dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.5996g is obtained, is E-3- (3,5- diformazans
Epoxide benzene methene base) -6- hydroxyl benzofurans -2 (3H) -one, yield 67%.
1H NMR(400MHz,DMSO-d6) δ 10.44 (s, 1H), 7.62 (d, J=8.4Hz, 1H), 7.53 (s, 1H), 6.90
(d, J=2.0Hz, 2H), 6.67 (d, J=2.0Hz, 1H), 6.63 (t, J=2.0Hz, 1H), 6.59 (dd, J=2.0,8.4Hz,
1H),3.79(s,6H)；13C NMR(100MHz,DMSO-d6)δ168.6,160.4,160.4,155.3,135.7,135.6,
123.9,121.4,112.1,111.2,106.8,102.1,98.4,55.2。
Embodiment 4：E-6- hydroxyls -3- (4- hydroxyl -3,5- dimethoxy benzene methenes base) benzofuran -2- (3H) -one
Synthesis
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (4- hydroxyl -3,5- dimethoxies are sequentially added
Base phenyl) acrylic acid (3mmol, 1.1856g), cupric sulfate pentahydrate (0.6mmol, 0.1498g), TMEDA (0.6mmol,
0.0698g), tripotassium phosphate (6mmol, 1.2736g), 20mL PEG-400, stir, under microwave condition, controlling reaction temperature 145
DEG C, react 4 minutes.After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, 3 are extracted with 30mL ethyl acetate
It is secondary, merge organic layer, organic layer is dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Obtain faint yellow solid
0.5563g, is E-6- hydroxyls -3- (4- hydroxyl -3,5- dimethoxy benzene methenes base) benzofuran -2- (3H) -one, yield
59%.
1H NMR(400MHz,DMSO-d6) δ 10.33 (s, 1H), 9.31 (s, 1H), 7.81 (d, J=8.8Hz, 1H), 7.53
(s, 1H), 7.11 (s, 2H), 6.67 (d, J=2.0Hz, 1H), 6.62 (dd, J=2.4,8.8Hz, 1H), 3.82 (s, 6H)；13C
NMR(100MHz,DMSO-d6)δ169.2,159.8,154.9,147.7,137.4,123.8,123.4,118.0,112.8,
111.0,110.0,107.5,98.4,55.8。
Embodiment 5：The synthesis of E-3- (4- hydroxy 3-methoxybenzene methenes base) benzofuran -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (2- bromophenyls) -3- (4- hydroxy 3-methoxybenzenes base) propylene is sequentially added
Sour (3mmol, 1.0475g), cuprous iodide (0.3mmol, 0.0571g), 8-hydroxyquinoline (0.3mmol, 0.0435g), carbonic acid
Sodium (6mmol, 0.6359g), 20mL PEG-400, stir, under microwave condition, 140 DEG C of controlling reaction temperature, the reaction time 20 divides
Clock.After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times, be associated with 30mL ethyl acetate
Machine layer, organic layer are dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.4990g is obtained, is E-3- (4-
Hydroxy 3-methoxybenzene methene base) benzofuran -2 (3H) -one, yield 62%.
1H NMR(400MHz,DMSO-d6) δ 10.10 (s, 1H), 7.95 (d, J=7.6Hz, 1H), 7.79 (s, 1H),
7.38-7.44 (m, 3H), 7.29 (d, J=8.0Hz, 1H), 7.20 (td, J=0.8,7.6Hz, 1H), 6.97 (d, J=8.0Hz,
1H),3.84(s,3H)；13C NMR(100MHz,DMSO-d6)δ168.8,153.3,150.1,147.6,142.2,130.4,
124.7,124.7,124.0,122.3,121.9,117.6,115.8,114.1,111.0,55.7。
Embodiment 6：The synthesis of E-3- (4- hydroxyl -3- ethoxybenzene methenes base) -6- hydroxyl benzofurans -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (4- hydroxyl -3- ethoxybenzenes are sequentially added
Base) acrylic acid (3mmol, 1.1376g), stannous chloride (0.6mmol, 0.0594g), glycine (0.6mmol, 0.0450g), carbon
Sour hydrogen sodium (6mmol, 0.5041g), 20mL PEG-400, stir, under microwave condition, 140 DEG C of controlling reaction temperature, react 6 points
Clock.After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times, be associated with 30mL ethyl acetate
Machine layer, organic layer are dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.6622g is obtained, is E-3- (4-
Hydroxyl -3- ethoxybenzene methenes base) -6- hydroxyl benzofurans -2 (3H) -one, yield 74%.
1H NMR(400MHz,DMSO-d6) δ 10.30 (s, 1H), 9.85 (s, 1H), 7.74 (d, J=8.4Hz, 1H), 7.51
(s, 1H), 7.29-7.32 (m, 2H), 6.95 (d, J=8.0Hz, 1H), 6.59-6.69 (m, 2H), 4.07 (q, J=8.0Hz,
2H), 1.37 (t, J=8.0Hz, 3H)；13C NMR(100MHz,DMSO-d6)δ169.4,159.9,154.9,149.5,146.8,
137.4,125.1,123.9,123.4,117.9,115.8,114.8,112.9,111.1,98.5,63.8,14.7。
Embodiment 7：The synthesis of E-6- hydroxyls -3- (4- trifluoromethylbenzene methenes base) benzofuran -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (4- trifluoromethyls) third is sequentially added
Olefin(e) acid (3mmol, 1.1615g), cuprous bromide (0.6mmol, 0.0861g), 1,10-phen (0.6mmol, 0.1189g), acetic acid
Sodium (6mmol, 0.4922g), 20mL PEG-400, stir, under microwave condition, 135 DEG C of controlling reaction temperature, the reaction time 8 divides
Clock.After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times, be associated with 30mL ethyl acetate
Machine layer, organic layer are dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.4410g is obtained, is E-6- hydroxyls
Base -3- (4- trifluoromethylbenzene methenes base) benzofuran -2 (3H) -one, yield 48%.
1H NMR(400MHz,DMSO-d6) δ 10.33 (s, 1H), 8.21 (d, J=8.4Hz, 2H), 7.88 (s, 1H), 7.82
(d, J=8.0Hz, 2H), 7.67 (d, J=8.0Hz, 1H), 6.66 (dd, J=2.0,8.4Hz, 1H), 6.61 (d, J=2.0Hz,
1H)。
Embodiment 8：The synthesis of E-3- (4- fluorobenzene methenes base) -6- hydroxyl benzofurans -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (4- fluorophenyls) acrylic acid is sequentially added
(3mmol, 1.0114g), thiophene -2-carboxylic acid cuprous (0.6mmol, 0.1144g), 1,10-phen (0.6mmol, 0.1189g),
Pyridine (8mmol, 0.6328g), 20mL PEG-400, stir, under microwave condition, 130 DEG C of controlling reaction temperature, react 6 minutes.
After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times with 30mL ethyl acetate, merged organic
Layer, organic layer are dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Faint yellow solid 0.3536g is obtained, is E-3- (4-
Fluorobenzene methene base) -6- hydroxyl benzofurans -2 (3H) -one, yield 46%.
1H NMR(400MHz,DMSO-d6) δ 10.41 (s, 1H), 7.81 (dd, J=5.6,8.4Hz, 2H), 7.58 (s,
1H), 7.55 (d, J=8.4Hz, 1H), 7.37 (t, J=8.8Hz, 2H), 6.66 (d, J=2.0Hz, 1H), 6.56 (dd, J=
2.0,8.4Hz,1H)；13C NMR(100MHz,DMSO-d6)δ168.7,162.7(1JC-F=247.6Hz), 160.6,155.4,
134.9,131.9(3JC-F=8.6Hz), 130.5 (4JC-F=2.5Hz), 123.7,121.2,116.0 (2JC-F=22.0Hz),
112.2,111.3,98.6。
Embodiment 9：The synthesis of E-3- (2,4- dichloro-benzenes methene base) -6- hydroxyl benzofurans -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (3,4- dichlorophenyl) propylene is sequentially added
Sour (3mmol, 1.1641g), copper acetate (0.6mmol, 0.1198g), 1,10-phen (0.6mmol, 0.1189g), triethylamine
(6mmol, 0.6071g), 20mL PEG-400, stir, under microwave condition, 140 DEG C of controlling reaction temperature, react 6 minutes.Reaction
After the completion of, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times with 30mL ethyl acetate, merge organic layer, have
Machine layer is dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Faint yellow solid 0.5897g is obtained, is E-3- (2,4- bis-
Chlorobenzene methene base) -6- hydroxyl benzofurans -2 (3H) -one, yield 64%.
1H NMR(400MHz,DMSO-d6) δ 10.52 (s, 1H), 7.85 (d, J=2.0Hz, 1H), 7.84 (d, J=
8.4Hz, 1H), 7.60 (dd, J=2.0,8.4Hz, 1H), 7.45 (s, 1H), 7.22 (d, J=8.8Hz, 1H), 6.67 (d, J=
2.0Hz, 1H), 6.53 (dd, J=2.0,8.4Hz, 1H)；13C NMR(100MHz,DMSO-d6)δ168.1,161.2,155.7,
135.1,134.1,131.3,131.2,129.7,129.5,127.9,124.2,123.9,111.7,111.6,98.6。
Embodiment 10：The synthesis of E-3- (4- hydroxy benzenes methenes base) -5- Methoxvbenzofurans -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 5- methoxyphenyls of 2-) -3- (4- hydroxy phenyls) propylene is sequentially added
Sour (3mmol, 1.0475g), cupric oxide (0.6mmol, 0.0477g), 1,10-phen (0.6mmol, 0.1189g), triethylamine
(6mmol, 0.6071g), 20mL dimethyl sulfoxides, stir, under microwave condition, 140 DEG C of controlling reaction temperature, react 6 minutes.Reaction
After the completion of, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times with 30mL ethyl acetate, merge organic layer, have
Machine layer is dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.6616g is obtained, is E-3- (4- hydroxy benzenes
Methene base) -5- Methoxvbenzofurans -2 (3H) -one, yield 76%.
1H NMR(400MHz,DMSO-d6) δ 10.41 (s, 1H), 7.77 (s, 1H), 7.73 (d, J=8.4Hz, 2H), 7.35
(d, J=2.4Hz, 1H), 7.21 (d, J=8.8Hz, 1H), 6.96-7.00 (m, 3H), 3.73 (s, 3H)；13C NMR(100MHz,
DMSO-d6)δ169.0,160.5,155.4,147.4,142.0,135.1,132.5,124.2,115.8,115.6,111.4,
107.4,104.6,55.5。
Embodiment 11：The synthesis of E-6- hydroxyls -3- (4- bromobenzene methenes base) benzofuran -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (4- bromophenyls) acrylic acid is sequentially added
(3mmol, 1.1942g), basic copper carbonate (0.6mmol, 0.1327g), 1,10-phen (0.6mmol, 0.1189g), triethylamine
(6mmol, 0.6071g), 20mL PEG-400, stir, under microwave condition, 150 DEG C of controlling reaction temperature, react 6 minutes.Reaction
After the completion of, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times with 30mL ethyl acetate, merge organic layer, have
Machine layer is dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.6565g is obtained, is E-6- hydroxyl -3- (4-
Bromobenzene methene base) benzofuran -2 (3H) -one, yield 69%.
1H NMR(400MHz,DMSO-d6) δ 10.46 (s, 1H), 7.75 (d, J=8.4Hz, 2H), 7.71 (d, J=
8.4Hz, 2H), 7.56 (d, J=8.0Hz, 1H), 7.55 (s, 1H), 6.67 (d, J=2.4Hz, 1H), 6.56 (dd, J=8.4,
2.4Hz,1H)；13C NMR(100MHz,DMSO-d6)δ168.7,160.8,155.5,134.5,133.2,131.9,131.3,
123.9,123.3,121.8,112.2,111.4,98.6。
Embodiment 12：The synthesis of E-6- hydroxyls -3- (4- nitrobenzene methenes base) benzofuran -2 (3H) -one
In 50mL microwave reaction bottles, E-2- (the bromo- 4- hydroxy phenyls of 2-) -3- (4- nitrobenzophenones) acrylic acid is sequentially added
(3mmol, 1.0925g), Kocide SD (0.6mmol, 0.0585g), 1,10-phen (0.6mmol, 0.1189g), triethylamine
(6mmol, 0.6071g), 20mL polyethylene glycol -200, stir, under microwave condition, 150 DEG C of controlling reaction temperature, react 20 points
Clock.After the completion of reaction, pour into 200mL water, pH=4 is acidified to watery hydrochloric acid, extracted 3 times, be associated with 30mL ethyl acetate
Machine layer, organic layer are dried with anhydrous magnesium sulfate.It is spin-dried for solvent, column chromatography purifying.Yellow solid 0.3909g is obtained, is E-6- hydroxyls
Base -3- (4- nitrobenzene methenes base) benzofuran -2 (3H) -one, yield 46%.
1H NMR(400MHz,DMSO-d6) δ 10.58 (s, 1H), 8.37 (d, J=8.4Hz, 2H), 7.99 (d, J=
8.4Hz, 2H), 7.65 (s, 1H), 7.52 (d.J=8.4Hz, 1H), 6.68 (d, J=2.0Hz, 1H), 6.57 (dd, J=8.4,
2.0Hz,1H)；13C NMR(100MHz,DMSO-d6)δ168.3,161.4,156.0,147.5,140.8,132.7,130.5,
124.4,124.0,124.0,111.9,111.6,98.7。
Claims (1)
- A kind of 1. method that different Aurone compound is prepared through Intra-molecular condensation, it is characterised in that：It is with E-2- (2- bromos Aryl) -3- aromatic substituted acrylic acid classes compound is raw material, under catalyst and part effect, presence and microwave reaction bar in alkali Under part, a period of time is reacted in solvent；After the completion of reaction, reaction solution is poured into water, is acidified to pH=3~4, is extracted, is done It is dry, solvent is spin-dried for, purifies, obtains different Aurone compound；Described catalyst is copper acetate, cupric oxide, basic copper carbonate, hydrogen Cupric oxide, copper sulphate, cupric sulfate pentahydrate, cuprous oxide, cuprous iodide, stannous chloride, cuprous bromide or thiophene -2-carboxylic acid are sub- Copper；Described part is DMAP, tetramethylethylenediamine, 8-hydroxyquinoline, 1,10- neighbour's phenanthroline or glycine； Described alkali is triethylene diamine, tripotassium phosphate, sodium carbonate, sodium acid carbonate, sodium acetate, caustic alcohol, pyridine or triethylamine；It is described Solvent be dimethyl sulfoxide (DMSO), N,N-dimethylformamide, polyethylene glycol -200 or PEG-4000；E-2- (2- bromos virtues Base) -3- aromatic substituted acrylic acid classes compound, catalyst, part, the ratio between the amount of material of alkali be 1：(0.05~0.3)：(0.05~ 0.3)：(1~3)；Reaction temperature is 130~150 DEG C, and the reaction time is 2~30 minutes.
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| CN102887879A (en) * | 2012-10-17 | 2013-01-23 | 江苏剑牌农化股份有限公司 | Method for synthesizing 2(3H)-benzofuranone by utilizing microwave |
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| CN102887879A (en) * | 2012-10-17 | 2013-01-23 | 江苏剑牌农化股份有限公司 | Method for synthesizing 2(3H)-benzofuranone by utilizing microwave |
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