CN108530445A - A kind of synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound - Google Patents
A kind of synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound Download PDFInfo
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention belongs to organic synthesis field, a kind of synthetic method of 3 cyanoimidazoles simultaneously [1,5 a] quinoline compound is disclosed.3 cyanoimidazoles simultaneously [1,5 a] quinoline compound synthetic method be temperature be 130 DEG C under conditions of, in oxygen atmosphere, using copper sulphate as catalyst, three component cascade reactions occur in a solvent for 2 methylquinoline compounds, amine compound and organic cyano source.After reaction, by isolating and purifying, imidazo [1,5 a] quinoline compound of No. 3 position cyano substitutions is obtained.The method of the present invention has the characteristics that easy to operate, raw material is cheap and easy to get, wide application range of substrates, high income, gathers around and has wide practical use in biological medicine, pesticide and optical material field.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of R1Substituted 2- methylquinolines compound, R2Substituted fat
Fat amine compounds and R3Substituted organic cyano source, under catalysis of cupric sulphate, the three component cascade reaction of generation of regioselectivity,
It is used to prepare imidazo [1,5-a] quinoline compound of 3- cyano substitution.
Background technology
Imidazo [1,5-a] quinolines are one kind to be had extensively in biological medicine, pesticide and optical material field
The nitrogen-containing heterocycle compound of application value.Various functional groups, energy are introduced in No. 3 positions of imidazo [1,5-a] quinolines
Significant impact is generated to its physics and chemistry and biological property, so as to improve its application performance.Therefore, by imidazo [1,5-
A] No. 3 position function dough of quinoline, it is increasingly closed to synthesize imidazo [1,5-a] quinoline compound containing various functional groups
Note.Cyano can easily be converted into the functional groups such as amido, amide, carboxylic acid as a flexible precursor.Cyano functional group is also wide
General is present in the structure of various bioactive molecules, can form interaction of hydrogen bond with biological targets, promote ligand and target
The biological interaction of point.Imidazo [1,5-a] pyridine of especially cyano substitution has various bioactivity, such as patent
2014171434 A1 of US disclose imidazo [1,5-a] pyridine of cyano substitution, and to can be used as somatostatin receptor 4 (SSTR4) short of money
Anti-agent, imidazo [1,5-a] pyridine that 2008108648 A1 of patent US disclose cyano substitution can be used as fibroblast life
The long factor (FGF) inhibitor, imidazo [1,5-a] pyridine that 2017129899 A1 of patent US disclose cyano substitution can be used as
Phosphatidyl-inositol 3-kinase γ (PI3K γ) inhibitor.However the research for synthesizing cyano substituted imidazole simultaneously [1,5-a] pyridine is less,
2011149921 A1 of patent US 20110021521 A1 and WO discloses the synthesis of cyanalation imidazo [1,5-a] pyridine,
It needs first to synthesize imidazo [1,5-a] pyridine parent nucleus, cyano substituted imidazole simultaneously [1,5- then could be prepared by multistep reaction again
A] pyridine, have the characteristics that cumbersome, total recovery is low.As the π derivatives of imidazo [1,5-a] pyridine, 3- cyanoimidazoles
And [1,5-a] quinoline may have similar or other potential bioactivity.But it is there is no at present about synthesis 3- cyanoimidazoles
And the report of [1,5-a] quinoline, to limit the research of subsequent structure-activity relation.
Invention content
The present invention provides a kind of synthetic methods of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound, and this method is with 2- first
Base quinoline compound, amine compound and organic cyano source are initial feed, to synthesize the imidazo of No. 3 position cyano substitutions
[1,5-a] quinoline.This invention the first elaborates the synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound, has anti-
Answer the features such as mild condition, raw material are cheap and easy to get, substrate spectrum is wide, high income.
A kind of synthetic method of 3- cyanoimidazoles of catalysis of cupric sulphate simultaneously [1,5-a] quinoline compound, including：By 2- methyl
Quinoline compound (II), amine compound (III), cyano sources (IV), copper sulphate, 1-Methyl-2-Pyrrolidone sequentially adds
Into reaction tube, after dissolving is stirred at room temperature, 130 DEG C is heated to, 12-24h is stirred to react.After reaction, reaction solution is cooled down
To room temperature, 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound (I) is obtained by isolating and purifying, reaction equation is shown below：
In above formula：R1For hydrogen, methyl, methoxyl group, ethyoxyl, nitro, phenyl or halogen；R2For aryl, aliphatic group or
Heterocycle：Wherein aryl be phenyl, it is o-methyl-phenyl, aminomethyl phenyl, p-methylphenyl, adjacent halogenophenyl, halogenophenyl, right
Halogenophenyl, o-methoxyphenyl, m-methoxyphenyl, p-methoxyphenyl, p-trifluoromethyl phenyl, to trifluomethoxybenzene
Base, p-hydroxybenzene, to cyano-phenyl；Aliphatic group is isopentyl；Heterocycle is pyridine, furans, thiophene；R3For phenyl or front three
Base silicon substrate.
Wherein, used catalyst is copper sulphate；It is carried out in oxygen atmosphere；Reaction dissolvent is 1- methyl -2- pyrroles
Alkanone (NMP)；Reaction temperature is 130 DEG C；Reaction time is 12-24h.
In above-mentioned reaction, the molar ratio of preferred raw material is：2- methylquinolines compound (II): amine compound
(III): cyano sources (IV): catalyst=1: 2: 2: 0.5.1-Methyl-2-Pyrrolidone is solvent.After the completion of reaction, it can be selected
The process that isolates and purifies include：Extraction, drying, rotary evaporation, column chromatography chromatogram obtain corresponding 3- cyanoimidazoles simultaneously [1,5-
A] quinoline compound.
Part 2- methylquinoline compounds used in above-mentioned synthetic method are the synthesis of existing method, other 2- first
Base quinoline compound, amine compound, cyano sources, copper sulphate and 1-Methyl-2-Pyrrolidone use commercial product.
This synthetic method the first elaborates the synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound, has anti-
The features such as answering wide mild condition, substrate spectrum, high income, gathers around in pharmaceutical field and has wide practical use.
Specific implementation mode
Embodiment 1-12
According to the raw material proportioning and reaction condition of Tables 1 and 2, sulfuric acid is added in the three mouthfuls of reaction tubes first dried to 20mL
Copper sequentially adds 2- methylquinolines compound (II), amine compound (III), cyano after vacuumizing displacement oxygen three times
Source (IV) and 1-Methyl-2-Pyrrolidone, mixed at room temperature stir evenly, and under oxygen atmosphere, are reacted according to the reaction condition of table 2
After the completion, reaction solution is cooled to room temperature, reaction solution is transferred in separatory funnel, 30 milliliters of water are added into separatory funnel,
Be extracted with ethyl acetate (3 × 10mL), anhydrous sodium sulfate drying after, through silica gel column chromatography separation (eluant, eluent be ethyl acetate with
The mixed liquor of petroleum ether, the two volume ratio are 1:4~8) corresponding 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound, is obtained
(I), reactional equation is shown below：
Table 1
Table 2
In table 2, CuSO4For anhydrous cupric sulfate, NMP is 1-Methyl-2-Pyrrolidone.
Structural characterization data
The structural characterization data of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound prepared by embodiment 1~12 are as follows：
The structure table of the 1- phenylimidazoles being prepared by embodiment 1 simultaneously [1,5-a] quinoline -3- carbonitrile compounds (I-1)
Levying data is：
1H-NMR(600MHz,DMSO-d6)δ8.01-8.00(m,1H),7.74(s,2H),7.69-7.66(m,3H),
7.64-7.62 (m, 2H), 7.53 (t, J=7.4Hz, 1H), 7.43-7.40 (m, 1H), 7.35 (d, J=8.6Hz, 1H)；13C-
NMR(150MHz,DMSO-d6)δ143.8,137.3,132.4,131.9,130.9,130.2,130.1,129.6,129.5,
128.1,126.9,125.3,117.1,115.7,114.7,104.4；HRMS(ESI)m/z[M+H]+calculated for
C18H12N3 270.1026,found 270.1028。
The knot of the fluoro- 1- phenylimidazoles of 7- being prepared by embodiment 2 simultaneously [1,5-a] quinoline -3- carbonitrile compounds (I-2)
Structure characterize data is：
1H-NMR (600MHz, DMSO-d6) δ 7.89-7.88 (m, 1H), 7.80 (d, J=9.4Hz, 1H), 7.70-7.67
(m,4H),7.65-7.62(m,2H),7.36-7.34(m,2H)；13C-NMR(150MHz,DMSO-d6)δ159.6(1JCF=
244.9Hz),143.7,136.9,132.1,131.0,130.1,129.6,128.6,127.33,127.30,127.2,119.3
(JCCCF=8.7Hz), 117.3,117.1,116.0,115.5,115.0,114.9,104.8；HRMS(ESI)m/z[M+H]+
calculated for C18H11N3F 288.0931,found 288.0933。
7- methyl-1s-phenylimidazole for being prepared by embodiment 3 simultaneously [1,5-a] quinoline -3- carbonitrile compounds (I-3)
Structural characterization data are：
1H-NMR(600MHz,DMSO)δ7.78(s,1H),7.70-7.61(m,7H),7.24-7.20(m,2H),2.38
(s,3H)；13C-NMR(150MHz,DMSO)δ143.5,137.2,136.5,132.4,130.8,130.6,130.1,129.9,
129.6,129.5,128.0,125.3,116.9,115.8,114.7,104.3,20.8；HRMS(ESI)m/z[M+H]+
calculated for C19H14N3 284.1182,found 284.1185。
By the knot for 8- chloro-1-phenyls imidazo [1,5-a] quinoline -3- carbonitrile compounds (I-4) that embodiment 4 is prepared
Structure characterize data is：
1H-NMR (600MHz, DMSO) δ 8.02 (d, J=8.4Hz, 1H), 7.77-7.70 (m, 5H), 7.67-7.65 (m,
2H), 7.60 (d, J=8.4Hz, 1H), 7.22 (s, 1H)；13C-NMR(150MHz,DMSO)δ143.9,137.2,133.5,
132.5,131.9,131.6,131.1,130.2,129.7,127.4,127.0,124.1,117.1,115.5,115.2,
104.5；HRMS(ESI)m/z[M+H]+calculated for C18H11N3Cl 304.0636,found 304.0638。
6,8- dimethyl -1- the phenylimidazoles being prepared by embodiment 5 simultaneously [1,5-a] quinoline -3- carbonitrile compounds (I-
5) structural characterization data are：
1H-NMR (600MHz, DMSO) δ 7.74 (d, J=9.6Hz, 1H), 7.70-7.66 (m, 1H), 7.64-7.60 (m,
5H),7.22(s,1H),6.94(s,1H),2.58(s,3H),2.06(s,3H)；13C-NMR(150MHz,DMSO)δ143.6,
138.8,137.2,136.9,132.6,132.1,130.7,130.1,129.4,129.3,124.4,121.5,115.8,
115.6,113.2,103.8,21.8,19.8；HRMS(ESI)m/z[M+H]+calculated for C20H16N3 298.1339,
found 298.1343。
9- methoxyl group -1- the phenylimidazoles being prepared by embodiment 6 simultaneously [1,5-a] quinoline -3- carbonitrile compounds (I-6)
Structural characterization data be：
1H-NMR(600MHz,DMSO)δ7.67-7.63(m,2H),7.54-7.53(m,2H),7.47-7.42(m,5H),
7.15(dd,J1=6.6Hz, J2=2.6Hz, 1H), 2.98 (s, 3H)；13C-NMR(150MHz,DMSO)δ149.1,147.6,
138.4,135.0,129.0,128.7,128.1,127.8,127.8,125.4,121.7,120.6,115.7,115.2,
112.6,105.1,54.3；HRMS(ESI)m/z[M+H]+calculated for C19H14ON3 300.1131,found
300.1133。
1- (4- chlorphenyls) imidazo [1,5-a] quinoline -3- carbonitrile compounds (I-7) being prepared by embodiment 7
Structural characterization data are：
1H-NMR (600MHz, DMSO) δ 8.01-8.00 (m, 1H), 7.78-7.74 (m, 4H), 7.54 (t, J=7.4Hz,
1H), 7.49-7.45 (m, 3H), 7.35 (d, J=8.5Hz, 1H)；13C-NMR(150MHz,DMSO)δ163.6(1JCF=
247.9Hz),142.8,137.3,132.7(3JCCCF=8.5Hz), 131.9,130.1,129.7,128.8 (4JCCCCF=
3.1Hz),128.1,126.9,125.3,117.1,116.7,116.6,115.7,114.7,104.3；HRMS(ESI)m/z[M+
H]+calculated for C18H11N3F 288.0932,found 288.0934。
1- (4- aminomethyl phenyls) imidazo [1,5-a] quinoline -3- carbonitrile compounds (I-8) being prepared by embodiment 8
Structural characterization data be：
1H-NMR (600MHz, DMSO) δ 7.98 (d, J=7.8Hz, 1H), 7.73-7.70 (m, 2H), 7.56 (d, J=
7.9Hz,2H),7.54-7.51(m,1H),7.44-7.41(m,4H),2.47(s,3H)；13C-NMR(150MHz,DMSO)δ
143.9,140.5,137.2,132.0,130.1,130.0,129.58,129.55,128.0,126.9,125.3,117.1,
115.7,114.7,104.3,21.5；HRMS(ESI)m/z[M+H]+calculated for C19H14N3 284.1182,found
284.1185。
1- (4- methoxyphenyls) imidazo [1,5-a] quinoline -3- carbonitrile compounds (I- being prepared by embodiment 9
9) structural characterization data are：
1H-NMR (600MHz, DMSO) δ 7.98 (d, J=7.7Hz, 1H), 7.70 (s, 2H), 7.60 (d, J=8.4Hz,
2H), 7.54-7.51 (m, 1H), 7.44 (d, J=3.4Hz, 2H), 7.17 (d, J=8.4Hz, 2H), 3.89 (s, 3H)；13C-NMR
(150MHz,DMSO)δ161.0,143.9,137.2,132.1,131.6,130.0,129.5,128.0,126.9,125.3,
124.4,117.0,115.8,114.9,114.7,104.2,55.8；HRMS(ESI)m/z[M+H]+calculated for
C19H14ON3 300.1131,found 300.1135。
1- (4- hydroxy phenyls) imidazo [1,5-a] quinoline -3- carbonitrile compounds (I- being prepared by embodiment 10
10) structural characterization data are：
1H-NMR(600MHz,DMSO)δ10.10(s,1H),7.98-7.96(m,1H),7.69(s,2H),7.53-7.51
(m,1H),7.48-7.44(m,4H),6.99-6.97(m,2H)；13C-NMR(150MHz,DMSO)δ159.5,144.3,137.1,
132.1,131.6,130.0,129.5,127.9,126.8,125.3,122.7,117.1,116.3,115.8,114.7,
104.1；HRMS(ESI)m/z[M+H]+calculated for C18H12N3O 286.0975,found 286.0977。
1- (2- furyls) imidazo [1,5-a] quinoline -3- carbonitrile compounds (I-11) being prepared by embodiment 11
Structural characterization data be：
1H-NMR (600MHz, DMSO) δ 8.08-8.04 (m, 2H), 7.79 (q, J=11.7Hz, 2H), 7.61-7.60 (m,
2H), 7.12 (d, J=2.9Hz, 1H), 7.02 (d, J=7.2Hz, 1H), 6.88 (s, 1H)；13C-NMR(150MHz,DMSO)δ
145.6,142.7,137.5,133.7,131.4,130.4,130.2,128.9,127.4,125.2,116.4,115.2,
115.1,114.6,112.8,105.0；HRMS(ESI)m/z[M+H]+calculated for C16H10ON3 260.0818,
found 260.0820。
1- (isobutyl group) imidazo [1,5-a] quinoline -3- carbonitrile compounds (I-12) being prepared by embodiment 12
Structural characterization data are：
1H-NMR (600MHz, DMSO) δ 8.32 (d, J=8.5Hz, 1H), 7.97 (dd, J1=8.0Hz, J2=1.3Hz,
1H), 7.79-7.77 (m, 1H), 7.62-7.58 (m, 3H), 3.27 (d, J=6.8Hz, 2H), 2.36-2.32 (m, 1H), 1.05
(d, J=6.6Hz, 6H)；13C-NMR(150MHz,DMSO)δ145.7,137.4,132.4,130.3,129.9,127.4,
126.7,125.3,117.7,116.0,114.7,102.9,40.4,26.2,22.8；HRMS(ESI)m/z[M+H]+
calculated for C16H16N3250.1339,found 250.1341。
Claims (6)
1. a kind of synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound, it is characterised in that：By catalyst, 2- methyl
Quinoline compound (II), amine compound (III), cyano sources (IV) and solvent are added sequentially in reaction tube, in oxygen atmosphere
Under enclosing, 130 DEG C are heated to, 12-24h is stirred to react, through isolating and purifying, obtains 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound
(I)；
The 3- cyanoimidazoles are simultaneously shown in [1,5-a] quinoline compound structure such as formula (I)：
Shown in the 2- methylquinolines compound structure such as formula (II)：
In formula (II)：R1For hydrogen, methyl, methoxyl group, ethyoxyl, nitro, phenyl or halogen；
Shown in the amine compound structure such as formula (III)：
In formula (III)：R2For aryl, aliphatic group or heterocycle：Wherein aryl be phenyl, it is o-methyl-phenyl, aminomethyl phenyl, right
Aminomethyl phenyl, adjacent halogenophenyl, halogenophenyl, to halogenophenyl, o-methoxyphenyl, m-methoxyphenyl, to methoxyl group
Phenyl, p-trifluoromethyl phenyl, to Trifluoromethoxyphen-l, p-hydroxybenzene, to cyano-phenyl；Aliphatic group is isopentyl；
Heterocycle is pyridine, furans, thiophene；
Shown in the cyano source structure such as formula (IV)：
R3-CN (IV)
In formula (IV)：R3For phenyl or trimethyl silicon substrate.
2. a kind of synthetic method of 3- cyanoimidazoles according to claim 1 simultaneously [1,5-a] quinoline compound, feature exist
In the material molar ratio is：2- methylquinolines compound (II): amine compound (III): cyano sources (IV): catalysis
Agent=1: 2: 2: 0.5.
3. a kind of synthetic method of 3- cyanoimidazoles according to claim 1 simultaneously [1,5-a] quinoline compound, feature exist
In the reaction temperature is preferably 130 DEG C, and the reaction time is preferably 12-24h.
4. a kind of synthetic method of 3- cyanoimidazoles according to claim 1 simultaneously [1,5-a] quinoline compound, feature exist
In the catalyst is copper sulphate.
5. a kind of synthetic method of 3- cyanoimidazoles according to claim 1 simultaneously [1,5-a] quinoline compound, feature exist
In the reaction environment atmosphere is oxygen.
6. a kind of synthetic method of 3- cyanoimidazoles according to claim 1 simultaneously [1,5-a] quinoline compound, feature exist
In the solvent is preferably 1-Methyl-2-Pyrrolidone (NMP).
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Cited By (1)
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|---|---|---|---|---|
| CN113735849A (en) * | 2021-07-22 | 2021-12-03 | 安徽中医药大学 | 1-cyano imidazo [1,5-a ] pyridine compound and synthetic method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106117203A (en) * | 2016-07-12 | 2016-11-16 | 安徽理工大学 | A kind of synthetic method of 3 arylthio Imidazoheterocyclic compounds |
| CN106188044A (en) * | 2016-07-05 | 2016-12-07 | 安徽理工大学 | A kind of synthetic method of 3 arylthio imidazos [1,5 a] the N heterocyclic compound of catalysis of iodine |
-
2018
- 2018-06-22 CN CN201810647183.4A patent/CN108530445A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106188044A (en) * | 2016-07-05 | 2016-12-07 | 安徽理工大学 | A kind of synthetic method of 3 arylthio imidazos [1,5 a] the N heterocyclic compound of catalysis of iodine |
| CN106117203A (en) * | 2016-07-12 | 2016-11-16 | 安徽理工大学 | A kind of synthetic method of 3 arylthio Imidazoheterocyclic compounds |
Non-Patent Citations (3)
| Title |
|---|
| XIAO CHEN ET AL.: ""Cu(II)-Catalyzed Functionalizations of Aryl C-H Bonds Using O2 as an Oxidant"", 《J. AM. CHEM. SOC.》 * |
| ZHENDA TAN ET AL.: ""Aerobic Copper-Catalyzed Halocyclization of Methyl N-Heteroaromatics with Aliphatic Amines: Access to Functionalized Imidazo-Fused N-Heterocycles"", 《J. ORG. CHEM.》 * |
| 魏红娟: ""铜催化咪唑并[1,5-a]N杂环类氰基衍生物的合成工艺"", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113735849A (en) * | 2021-07-22 | 2021-12-03 | 安徽中医药大学 | 1-cyano imidazo [1,5-a ] pyridine compound and synthetic method thereof |
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