CN117164534A - Preparation method of benzofuran derivative containing acetamide structure - Google Patents
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- CN117164534A CN117164534A CN202311004198.6A CN202311004198A CN117164534A CN 117164534 A CN117164534 A CN 117164534A CN 202311004198 A CN202311004198 A CN 202311004198A CN 117164534 A CN117164534 A CN 117164534A
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- 150000001907 coumarones Chemical class 0.000 title claims abstract description 45
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 14
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 claims abstract description 12
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims abstract description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 9
- 125000002346 iodo group Chemical group I* 0.000 claims abstract description 9
- 239000011733 molybdenum Substances 0.000 claims abstract description 9
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 7
- 229910000160 potassium phosphate Inorganic materials 0.000 claims abstract description 6
- 235000011009 potassium phosphates Nutrition 0.000 claims abstract description 6
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- -1 trifluoromethoxy, methyl Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- LKYMWFDXBHLYNJ-UHFFFAOYSA-N 3-iodo-3-(1-iodoprop-2-ynoxy)prop-1-yne Chemical compound C#CC(I)OC(I)C#C LKYMWFDXBHLYNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 6
- 125000000524 functional group Chemical group 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000003638 chemical reducing agent Substances 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- 238000001514 detection method Methods 0.000 description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
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- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of benzofuran derivatives containing an acetamide structure, which comprises the following steps: palladium acetate, tricyclohexylphosphine, molybdenum carbonyl, potassium phosphate, water, iodo arene propargyl ether and nitroarene are reacted for 24 hours at 100 ℃, and after the reaction is completed, the benzofuran derivative containing an acetamide structure is obtained through post treatment. According to the preparation method, nitroarene is used as a nitrogen source, and molybdenum carbonyl is used as a carbonyl source and a reducing agent, so that the operation is simple, the initial raw materials of the reaction are cheap and easy to obtain, the tolerance range of the substrate functional group is wide, and the reaction efficiency is high. Can synthesize various benzofuran derivatives containing acetamide structures according to actual needs, is convenient to operate and widens the practicability of the method.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of benzofuran derivatives containing an acetamide structure.
Background
The construction of heterocyclic compounds having different functional groups by one-step reactions plays an important role in the fields of biology, medicine and material science (Angew.Chem., int.Ed.,2022,61, e 202112288). Thus, the search for simple, straightforward methods for synthesizing heterocyclic products with a variety of functional groups is of great importance in organic chemistry. Among them, benzofuran derivatives are a class of structurally specific and very valuable backbone molecules, which are widely found in many natural products and exhibit a variety of biological and pharmaceutical activities. In addition, amide compounds are often found in a variety of natural products, drugs and bioactive molecules as useful components in life sciences. Because of their particular biological and synthetic advantages, the linking of benzofurans and amides in one molecule would have important applications in pharmaceutical chemistry, with the expectation that heterocyclic compounds with pharmaceutical and biological activity would be obtained.
In recent years, significant progress has been made in the synthesis of carbocyclic and heterocyclic compounds by alkyne cyclization, starting from simple and readily available substrates (chem.rev., 2014,114,1783-1826). In particular, palladium-catalyzed cyclization of aryl propargyl ethers has attracted considerable attention as a powerful and efficient synthetic method for preparing benzofuran derivatives. From the mechanism, the reaction firstly obtains an active alkenyl palladium intermediate through intramolecular palladium on carbon of alkyne, and then obtains heterocyclic compounds with various structures through subsequent various conversions. However, most of the above reactions mainly produce 2, 3-dihydrobenzofuran products, and there are very limited examples of synthesizing structurally defined benzofuran derivatives. Since palladium catalyzed carbonylation is one of the most powerful methods of constructing carbonyl-containing compounds, it has the advantages of being efficient, straightforward and atom-economical. Thus, we believe that palladium-catalyzed alkyne cyclization/carbonylation reactions would be an ideal strategy for preparing heterocyclic compounds containing carbonyl structures.
Based on this, we developed a palladium-catalyzed cyclization/carbonylation reaction to synthesize benzofuran derivatives containing acetamide structures. The method starts from simple and easily obtained iodo arene propargyl ether and nitroarene compounds, takes molybdenum carbonyl as a carbonyl source and a reducing agent, takes nitroarene as a nitrogen source, synthesizes a plurality of benzofuran derivatives containing an acetamide structure, and provides a new synthesis path for the reaction of synthesizing benzofuran derivatives containing an acetamide structure by carbonyl.
Disclosure of Invention
The invention provides a preparation method of benzofuran derivatives containing an acetamide structure, which has the advantages of simple steps, low-cost and easily-obtained reaction raw materials, compatibility with various functional groups, good reaction applicability, and provides a new direction for synthesizing benzofuran derivatives containing an acetamide structure by taking nitroarene as a nitrogen source and molybdenum carbonyl as a carbonyl source and a reducing agent.
A process for the preparation of benzofuran derivatives containing an acetamide structure comprising the steps of: reacting a palladium catalyst, tricyclohexylphosphine, molybdenum carbonyl, potassium phosphate, water, iodo arene propargyl ether and nitroarene for 20-28 hours at 90-110 ℃, and after the reaction is completed, carrying out post-treatment to obtain the benzofuran derivative containing an acetamide structure;
the structure of the iodo arene propargyl ether is shown in a formula (II):
the structure of the nitroarene is shown in a formula (III):
Ar 2 -NO 2 (III)；
the structure of the benzofuran derivative containing the acetamide structure is shown as a formula (I):
in the formulae (I) to (III), R is hydrogen or halogen, ar 1 ，Ar 2 Independently phenyl or substituted phenyl;
the substituent on the phenyl is trifluoromethoxy and C 1 ～C 4 Alkyl, phenyl, C 1 ～C 4 Alkylthio, C 1 ～C 4 Alkoxy, dimethylamino, trifluoromethyl, cyano, cl, F or bromo.
The molar ratio of the palladium catalyst to the tricyclohexylphosphine to the potassium phosphate is 0.02:0.04:2;
the substitution position of R is meta; ar (Ar) 1 Is para to the position of substitution on the phenyl group, ar 2 The substitution position on the phenyl group is para or ortho.
The reaction formula is as follows:
in the invention, the optional post-treatment process comprises: filtering, mixing with silica gel, and purifying by column chromatography to obtain benzofuran derivative containing acetamide structure.
Preferably, R is hydrogen or Cl, ar 1 Is phenyl or substituted phenyl, and the substituent on the phenyl is trifluoromethoxy, methyl, phenyl, cl or bromine. At this time, the iodo arene propargyl ether was easily obtained, and the yield of the reaction was high.
Preferably Ar 2 Is phenyl or substituted phenyl, and the substituent on the phenyl is methyl, thiomethyl, N-dimethyl, methoxy, trifluoromethyl, cyano, F or Br. At this time, the nitroaromatic hydrocarbon is easily obtained, and the yield of the reaction is high.
The iodoaromatic propargyl ether and nitroaromatic hydrocarbon used for preparing the benzofuran derivative containing the acetamide structure are low in price and widely exist in the nature, and the iodoaromatic propargyl ether is preferred in terms of molar amount: nitroaromatics: palladium catalyst=2 to 2.5:1:0.05 to 0.1; as a further preference, the iodo arene propargyl ether is calculated on a molar basis: nitroaromatics: palladium catalyst=2:1:0.1.
Preferably, the reaction time is 24 hours, and the reaction time is too long to increase the reaction cost, but on the contrary, it is difficult to ensure the completion of the reaction.
Preferably, the reaction is carried out in acetonitrile in an amount to provide good dissolution of the starting materials, with 0.4mmol of iodoaromatic propargyl ether using an amount of acetonitrile of about 1 to 2mL.
Preferably, the palladium catalyst is palladium acetate, and among a plurality of palladium catalysts, palladium acetate is relatively inexpensive, and the reaction efficiency is relatively high when palladium acetate is used as the catalyst.
As a further preferred aspect, the benzofuran derivative having an acetamide structure is one of the compounds of formula (I-1) -formula (I-5):
in the preparation method, the nitroarene, the molybdenum carbonyl, the palladium acetate, the tricyclohexylphosphine and the potassium phosphate are generally commercially available products and can be conveniently obtained from the market.
Compared with the prior art, the invention has the beneficial effects that: the nitroarene is used as a nitrogen source, the preparation method is simple, the operation is easy, the post-treatment is simple and convenient, the reaction starting materials are cheap and easy to obtain, the tolerance range of the substrate functional group is wide, and the reaction efficiency is high. Can synthesize various benzofuran derivatives containing acetamide structures according to actual needs, and has strong practicability.
Detailed Description
The invention is further described below in connection with specific embodiments.
Examples 1 to 15
Palladium acetate, tricyclohexylphosphine, molybdenum carbonyl, potassium phosphate, water, iodo arene propargyl ether (II) and nitroarene (III) are added into a 15mL sealed tube according to the raw material ratio of the table 1, acetonitrile (1 mL) is then added, the mixture is uniformly mixed and stirred, the mixture reacts according to the reaction conditions of the table 2, after the reaction is completed, the mixture is filtered, silica gel is stirred, and the corresponding benzofuran derivative (I) containing an acetamide structure is obtained through column chromatography purification, wherein the reaction process is shown as the following formula:
TABLE 1 amounts of raw materials to be added in examples 1 to 15
TABLE 2
In tables 1 and 2, T is the reaction temperature, T is the reaction time, ph is phenyl, OCF 3 Is trifluoromethoxy, me is methyl, SMe is methylthio, NMe 2 Is N, N-dimethyl, OMe is methoxy, CF 3 Is trifluoromethyl and CN is cyano.
Structure confirmation data for the compounds prepared in examples 1 to 5:
nuclear magnetic resonance of benzofuran derivative (I-1) having an acetamide structure prepared in example 1 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,CDCl 3 )δ7.59(s,1H),7.51–7.49(m,2H),7.43(d,J＝7.5Hz,2H),7.39–7.33(m,5H),7.31–7.28(m,2H),7.17(t,J＝7.5Hz,1H),7.08(d,J＝8.0Hz,2H),5.11(s,1H),2.29(s,3H).
13 C NMR(101MHz,CDCl 3 )δ169.0,155.6,143.8,137.7,135.0,134.5,129.6,129.2,128.6,128.1,127.1,124.9,123.0,120.2,120.1,119.0,111.8,50.9,21.0.
nuclear magnetic resonance of benzofuran derivative (I-2) having acetamide Structure prepared in example 2 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,CDCl 3 )δ7.58(s,1H),7.51–7.49(m,2H),7.43–7.41(m,2H),7.39–7.36(m,5H),7.33–7.28(m,2H),7.19(d,J＝8.6Hz,3H),5.11(s,1H),2.44(s,3H).
13 C NMR(101MHz,CDCl 3 )δ169.1,155.7,143.9,137.6,135.2,134.4,129.3,128.6,128.2,128.0,127.0,124.9,123.1,120.8,120.0,118.9,111.9,50.9,16.8.
nuclear magnetic resonance of benzofuran derivative (I-3) having an acetamide structure prepared in example 3 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,CDCl 3 )δ7.58(s,1H),7.51–7.47(m,2H),7.44–7.42(m,2H),7.41–7.36(m,5H),7.34–7.33(m,1H),7.32–7.29(m,1H),7.18(t,J＝7.5Hz,1H),6.97(t,J＝8.6Hz,2H),5.12(s,1H).
13 C NMR(101MHz,CDCl 3 )δ169.2,159.8(C-F,d, 1 J C-F ＝244.3Hz),155.7,143.9,137.5,133.5(C-F,d, 4 J C-F ＝2.4Hz),129.3,128.6,128.2,127.0,125.0,123.1,122.1(C-F,d, 3 J C-F ＝7.9Hz),120.0,118.8,115.8(C-F,d, 2 J C-F ＝22.5Hz),111.9,50.8.
nuclear magnetic resonance of benzofuran derivative (I-4) having an acetamide structure prepared in example 4 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,CDCl 3 )δ7.59(s,1H),7.54–7.42(m,4H),7.39–7.36(m,1H),7.35–7.29(m,3H),7.23–7.17(m,3H),7.09(d,J＝8.1Hz,2H),5.10(s,1H),2.30(s,3H).
13 C NMR(101MHz,CDCl 3 )δ168.6,155.7,148.9,143.8,136.3,134.8,130.1,129.7,126.7,125.1,123.2,121.5,120.6(C-F,q, 1 J C-F ＝257.5Hz),120.3,119.9,118.6,112.0,50.0,21.0.
nuclear magnetic resonance of benzofuran derivative (I-5) having an acetamide structure prepared in example 5 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,CDCl 3 )δ7.62(s,1H),7.54(d,J＝8.3Hz,1H),7.42–7.37(m,5H),7.37–7.33(m,4H),7.22(t,J＝7.5Hz,1H),7.13(d,J＝8.1Hz,2H),5.10(s,1H),2.33(s,3H).
13 C NMR(101MHz,CDCl 3 )δ168.5,155.7,143.8,136.2,134.9,134.8,134.0,130.0,129.7,129.4,126.8,125.1,123.2,120.3,120.0,118.7,112.0,50.2,21.0。
Claims (9)
1. a process for the preparation of benzofuran derivatives having an acetamide structure comprising the steps of: reacting palladium catalyst, ligand, molybdenum carbonyl, alkali, water, iodo arene propargyl ether and nitroarene at 90-110 ℃ for 20-28 hours, and after the reaction is completed, carrying out post-treatment to obtain the benzofuran derivative containing the acetamide structure;
the structure of the iodo arene propargyl ether is shown in a formula (II):
the structure of the nitroarene is shown in a formula (III):
Ar 2 -NO 2 (III)；
the structure of the benzofuran derivative containing the acetamide structure is shown as a formula (I):
in the formulae (I) to (III), R is hydrogen or halogen, ar 1 ，Ar 2 Independently phenyl or substituted phenyl;
the substituent on the phenyl is trifluoromethoxy and C 1 ～C 4 Alkyl, phenyl, C 1 ～C 4 Alkylthio, C 1 ～C 4 Alkoxy, dimethylamino, trifluoromethyl, cyano, cl, F or bromo.
2. The process for preparing benzofuran derivatives having an acetamide structure according to claim 1, wherein R is hydrogen or Cl, ar 1 Is phenyl or substituted phenyl, and the substituent on the phenyl is trifluoromethoxy, methyl, phenyl, cl or bromine.
3. The process for producing benzofuran derivatives having an acetamide structure according to claim 1, wherein Ar is 2 Is phenyl or substituted phenyl, and the substituent on the phenyl is methyl, methylthio, dimethylamino, methoxy, trifluoromethyl, cyano, F or Br.
4. The process for the preparation of benzofuran derivatives containing an acetamide structure according to claim 1, wherein the aromatic iodo propargyl ether is present in molar amounts: nitroaromatics: molybdenum carbonyl: palladium catalyst: ligand: alkali: water=2 to 2.5:1:1.5 to 2:0.1 to 0.2:0.2 to 0.4:1.5 to 2:1 to 1.5.
5. The process for producing a benzofuran derivative having an acetamide structure according to claim 1, wherein acetonitrile is used as a solvent.
6. The process for producing benzofuran derivatives having an acetamide structure according to claim 1, wherein the palladium catalyst is palladium acetate.
7. The process for the preparation of benzofuran derivatives having an acetamide structure according to claim 1 wherein the ligand is tricyclohexylphosphine.
8. The process for producing benzofuran derivatives having an acetamide structure according to claim 1, wherein the base is potassium phosphate.
9. The process for the preparation of benzofuran derivatives having an acetamide structure according to claim 1, wherein the benzofuran derivative having an acetamide structure is one of the compounds of formula (I-1) -formula (I-5):
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