CN109651271B - Synthetic method of 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound - Google Patents
Synthetic method of 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title description 2
- -1 tert-butyl hydrazino ester Chemical class 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 8
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims abstract description 8
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- 238000005580 one pot reaction Methods 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 10
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 6
- CHPVQLYVDDOWNT-UHFFFAOYSA-N 1-methylquinoxalin-2-one Chemical compound C1=CC=C2N=CC(=O)N(C)C2=C1 CHPVQLYVDDOWNT-UHFFFAOYSA-N 0.000 claims description 5
- TTWXWIIEDVZTEB-UHFFFAOYSA-N C1=CC=C2N=C(C(C)(C)C)C(=O)N(C)C2=C1 Chemical compound C1=CC=C2N=C(C(C)(C)C)C(=O)N(C)C2=C1 TTWXWIIEDVZTEB-UHFFFAOYSA-N 0.000 claims description 5
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 8
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 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
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005954 phosphonylation reaction Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000006692 trifluoromethylation reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a synthesis method of a 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound, which is characterized in that N-methylquinoxaline-2 (1H) -ketone, tert-butyl hydrazino ester and persulfate are reacted in one pot to synthesize the 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound in an air atmosphere. The method has the characteristics of easily obtained raw materials, simple and convenient operation, mild reaction conditions, high reaction regioselectivity, high yield and the like.
Description
Technical Field
The invention relates to a method for synthesizing a 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound, in particular to a method for synthesizing a 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound in a high-region selectivity by directly oxidizing, removing hydrazine, carboxyl and substituting C-3 hydrogen in an air atmosphere by taking hydrazino-tert-butyl ester as a tert-butyl source, belonging to the technical field of synthesis of organic intermediates.
Background
The quinoxaline-2 (1H) -ketone compound is a common pharmacophore in the field of pharmaceutical research, and the derivative with the parent structure has various physiological and pharmacological activities, is widely used as an anticancer drug, an antitumor drug, an antibacterial drug and the like, is a potential multipurpose lead compound, and has wide development and application prospects. Indeed, the quinoxalinone and modified functional groups on the parent quinoxalinone structure together affect the drug and biological activity of the molecule, not just the parent quinoxalinone structure itself. Therefore, modification of various substituents on the parent quinoxalinone structure and study of the structure-activity relationship are becoming hot points of study. In the past few years, considerable progress has been made in the functionalization of quinoxaline-2 (1H) -ones with C3, including C-H bond alkylation, arylation, acylation, amination, azidation, quinolination, trifluoromethylation, phosphonylation, and the like.
The current invention patents (CN1949966A, US 20050256000) only issued in 2010 about 3-tert-butyl quinoxaline-2 (1H) -ketone compounds by Bayer crop science Co., Ltd disclose quinoxaline-2-ketone derivatives, crop protection agents containing the compounds, and preparation methods and applications thereof, but the synthesis methods of 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compounds are not reported in documents.
Disclosure of Invention
Aiming at the technical blank existing in the synthesis of 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compounds in the prior art, the invention aims to provide a method for synthesizing 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compounds in high regioselectivity by reacting N-methylquinoxaline-2 (1H) -ketone, hydrazino tert-butyl ester and potassium persulfate under the air atmosphere.
In order to achieve the technical purpose, the invention provides a synthesis method of 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound, which comprises the steps of carrying out one-pot reaction on N-methylquinoxaline-2 (1H) -ketone, hydrazino tert-butyl ester and persulfate to generate the 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound in an air atmosphere;
the N-methylquinoxaline-2 (1H) -one compound has a structure shown in a formula 1;
the tert-butyl hydrazino ester has a structure of formula 2:
the 3-tert-butyl-N-methylquinoxaline-2 (1H) -one compound has the structure of formula 3:
in a preferred embodiment, the molar ratio of the N-methylquinoxaline-2 (1H) -one compound, the tert-butyl hydrazino ester and the persulfate is 1: 1-2: 2 to 4. The most preferred molar ratio is 1: 1.5: 3.
in a preferred embodiment, the persulfate is potassium persulfate. A large number of experiments show that other common persulfates such as sodium persulfate, ammonium persulfate and the like can not meet the requirements.
In a preferred embodiment, the reaction conditions are: reacting for 3-12 hours at 80-100 ℃. Most preferably at 85-95 ℃ for 3-5 hours.
In a preferred embodiment, the reaction employs acetonitrile as a reaction medium, the acetonitrile is a benign solvent in the technical scheme of the invention, and other common solvents such as methanol, Dichloroethane (DCE) and N, N-Dimethylformamide (DMF) are non-benign solvents.
In a preferred scheme, the molar concentration of the N-methylquinoxaline-2 (1H) -ketone compound in the acetonitrile reaction medium is 0.1 to 0.3 mmol/mL. The most preferred molar concentration is 0.2 mmol/mL.
The route of the addition reaction of N-methylquinoxaline-2 (1H) -ketone compound, tert-butyl hydrazino ester and potassium persulfate is as follows:
the invention also provides a reasonable reaction mechanism. The reaction of tert-butyl hydrazino with N-methylquinoxalin-2 (1H) -one is illustrated by way of example. Hydrazino tert-butyl ester (2) with sulfate anion radical (generated in situ from persulfate anion cleavage) to form tert-butyl radical and release HSO4 -Anions, molecular nitrogen and carbon dioxide. Tert-butyl radical attack of C3 into N-methylquinoxaline-2 (1H) -one (1) forms a radical intermediate (A) which is subsequently hydrogen-abstracted/oxidized by sulfate anions to give the desired product (3).
Compared with the prior art, the technical scheme of the invention has the beneficial technical effects that:
1) the invention synthesizes the 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound by one step through addition reaction of N-methylquinoxaline-2 (1H) -ketone, hydrazino-tert-butyl ester and potassium persulfate for the first time.
2) The invention adopts tert-butyl carbazyl ester as a tert-butyl source and potassium persulfate as an oxidant, and has the advantages of easily obtained sources and low cost;
3) the invention does not use transition metal and various acid-base additives, has high reaction region selectivity, and is easy to separate and purify the product.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of 3-tert-butyl-N-methylquinoxalin-2 (1H) -one;
FIG. 2 is a nuclear magnetic carbon spectrum of 3-tert-butyl-N-methylquinoxalin-2 (1H) -one.
Detailed Description
The following specific examples are intended to further illustrate the present disclosure, but not to limit the scope of the claims.
Comparative example:
the following control experiment groups 1 to 16 all react according to the following reaction equation:
the specific operation steps are as follows: in a 5mL round-bottom flask, N-methylquinoxaline-2 (1H) -ketone (1 equivalent, 0.1mmol), tert-butyl hydrazino ester, an oxidant and a solvent are sequentially added, and the obtained mixed solution reacts in a heating and stirring reaction device. The reaction progress is followed by a thin layer chromatography plate, after the reaction is finished, the reaction is cooled to room temperature, 3ml of water is added for dilution, the reactant is extracted by ethyl acetate, and the yield is analyzed by nuclear magnetic crude spectrum.
In the table, experimental groups 1-6 investigate the influence of various oxidants on the addition reaction of N-methylquinoxaline-2 (1H) -ketone and tert-butyl hydrazino, and experimental data show that the reaction is very sensitive to the types of oxidants, and the ideal product yield can be obtained only by using potassium persulfate.
In the table, experimental groups 1 and 7-12 investigate the influence of the reaction medium on the addition reaction of the N-methylquinoxaline-2 (1H) -ketone and the tert-butyl hydrazino, and experiments show that acetonitrile is the optimal reaction medium for the reaction.
In the table, experimental groups 1 and 13-14 investigate the influence of the use amount of tert-butyl hydrazino ester on the addition reaction of N-methylquinoxaline-2 (1H) -ketone and tert-butyl hydrazino ester, and experiments show that the optimum molar use amount of tert-butyl hydrazino ester is 1.5 equivalent, the yield of the target product is not obviously increased when the molar use amount is too high, and the yield of the target product is obviously reduced when the molar use amount is too low.
In the table, experiment groups 1 and 15-16 investigate the influence of the dosage of potassium persulfate serving as an oxidant on the addition reaction of N-methylquinoxaline-2 (1H) -ketone and tert-butyl hydrazino, and experiments show that the optimal dosage of potassium persulfate is 3 equivalents, the yield of a target product is not obviously increased when the dosage is too high, and the yield of the target product is obviously reduced when the dosage is too low.
In the above table, experimental groups 1 and 17-18 investigate the influence of the molar concentration of N-methylquinoxaline-2 (1H) -ketone on the addition reaction of N-methylquinoxaline-2 (1H) -ketone and tert-butyl hydrazino ester, and experiments show that the molar concentration of the quinoxaline-2 (1H) -ketone derivative is 0.2mmol/mL, which is the optimum substrate molar concentration for the reaction, when the molar concentration is too high, the yield of the target product is not obviously increased, and when the molar concentration is too low, the yield of the target product is obviously reduced.
In the table, experiment groups 1 and 19-20 investigate the influence of the reaction temperature on the addition reaction of the N-methylquinoxaline-2 (1H) -ketone and the tert-butyl hydrazino, and experiments show that the reaction temperature is the optimum reaction temperature at 90 ℃, the yield of the target product is not obviously increased when the reaction temperature is too high, and the yield of the target product is obviously reduced when the reaction temperature is too low.
Example 1
The specific operation steps are as follows: in a 10mL round-bottom flask, quinoxaline-2 (1H) -one derivative (1 equivalent, 0.5mmol), hydrazino-tert-butyl ester (1.5 equivalent, 7.5mmol), potassium persulfate (3 equivalent, 1.5mmol) and acetonitrile (2.5mL) were added in this order, and the resulting mixture was heated and stirred under air at 90 ℃ for 4 hours. After the reaction is finished, cooling to room temperature, adding 3ml of water for dilution, extracting a reactant by ethyl acetate, performing nuclear magnetic crude spectrum analysis on the yield, concentrating the filtrate by using a rotary evaporator, and performing column chromatography purification by using Petroleum Ether (PE)/Ethyl Acetate (EA) as an eluent and silica gel (200-mesh and 300-mesh sieve).
The obtained product is: 3-tert-butyl-N-methylquinoxalin-2 (1H) -one; the yield was 85%.
1H NMR(400MHz,CDCl3):δ＝7.83(dd,J1＝8.4Hz,J2＝1.2Hz,1H),7.52–7.48(m,1H),7.33–7.25(m,2H),3.67(s,3H),1.49(s,9H)；
13C NMR(100MHz,CDCl3):δ＝165.3,153.7,133.3,132.2,130.1,129.5,123.1,113.2,39.4,28.7,27.9；
HRMS(ESI)m/z calcd.for C13H17N2O[M+H]+:217.1335,found 217.1332.
Claims (4)
1. A method for synthesizing 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound is characterized in that: in the air atmosphere, N-methylquinoxaline-2 (1H) -ketone, hydrazino tert-butyl ester and persulfate react in one pot to generate a 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound;
the tert-butyl hydrazino ester has a structure of formula 2:
the persulfate is potassium persulfate;
the reaction employs acetonitrile as a reaction medium.
2. The process according to claim 1 for synthesizing 3-tert-butyl-N-methylquinoxalin-2 (1H) -one, wherein: the molar ratio of the N-methylquinoxaline-2 (1H) -one to the hydrazino tert-butyl ester to the persulfate is 1: 1-2: 2 to 4.
3. The method for synthesizing 3-tert-butyl-N-methylquinoxalin-2 (1H) -one compound according to any one of claims 1 to 2, characterized in that: the reaction conditions are as follows: reacting for 3-12 hours at 80-100 ℃.
4. The process according to claim 1 for synthesizing 3-tert-butyl-N-methylquinoxalin-2 (1H) -one, wherein: the molar concentration of the N-methylquinoxaline-2 (1H) -ketone in the acetonitrile reaction medium is 0.1-0.3 mmol/mL.
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| CN110642798B (en) * | 2019-11-10 | 2020-07-24 | 湖南科技学院 | Green synthesis method of N-substituted-1, 4-dihydro-2, 3-quinoxalinedione compound |
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