CN105924483A - Method for preparing 2-glycosyl substituted pyrazol[1,5-c]quinazoline framework compound through silver catalysis - Google Patents

Method for preparing 2-glycosyl substituted pyrazol[1,5-c]quinazoline framework compound through silver catalysis Download PDF

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CN105924483A
CN105924483A CN201610343687.8A CN201610343687A CN105924483A CN 105924483 A CN105924483 A CN 105924483A CN 201610343687 A CN201610343687 A CN 201610343687A CN 105924483 A CN105924483 A CN 105924483A
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quinazoline
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王涛
冯海燕
黄阳妃
袁淋
余维洁
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Jiangxi Normal University
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Abstract

The invention provides a method for preparing a 2-glycosyl substituted pyrazol[1,5-c]quinazoline framework compound through silver catalysis. The structure of the compound is represented through the methods of 1H NMR, 13C NMR, MS and the like and confirmed. A 1,3-dipolar quinazoline dipolar compound prepared through the reaction of a series of compounds of nitrobenzaldehyde and triethyl orthoformate and end alkyne sugar prepared from a series of compounds such as sugar and propargyl alcohol react under catalysis of Ag2O at the temperature of 70 DEG C under N2 protection with DBU as alkali and NMP as a solvent to generate a series of 2-glycosyl substituted pyrazol[1,5-c]quinazoline derivatives. The glycosyl modified pyrazol[1,5-c]quinazoline framework compound can be efficiently prepared through the reaction. The method is moderate in reaction condition, operation is simple, and purification of the product is convenient. A glycosyl modified nitrogen heterocyclic ring compound framework has broad-spectrum pharmacological activity, and has good application prospects in the field of new drug research and development.

Description

The method that 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound is prepared in silver catalysis
Technical field
The present invention relates to organic chemistry, carbohydrate chemistry field, be specifically related to glycosyl substituted pyrazolo [1,5-c] quinazoline compounds Synthetic method.
Background technology
Nitrogen-containing heterocycle compound is the compound that a class has pharmacologically active, is widely present in nature and the world of medicine, particularly contains There is the compound of quinazoline skeleton, in many alkaloidss and the medicine that listed, all there is this kind of skeleton, such as at malaria Disease, resisting hypertension, sterilization, anticancer etc. aspect all show obvious biological activity (Shen, G.；Zhou,H.；Sui,Y.；Liu, Q.；Zou,K.Tetrahedron Letters 2016,57,587；Mhaske,S.B.；Argade,N.P.Tetrahedron 2006,62, 9787.), there is important research and using value.Just because of quinazoline compounds, there is the best application prospect, Many research worker are devoted to the research to this structure.Such as 2011, the scientific research personnel such as Jan Kehler studied and has synthesized a class Novel pyrazolo [1,5-c] quinazoline compounds, has filtered out phosphoric acid in a series of quinazoline compound obtained Diesterase 10A has compound scaffold (Asproni, the B. of good inhibitory action；Murineddu,G.；Pau,A.；Pinna,G.A.； Langgard,M.；Christoffersen,C.T.；Nielsen,J.；Kehler,J.Bioorganic&medicinal chemistry 2011, 19,642.) and in recent years, also there are many documents to report and modify various heterocyclic compound with glycosyl, these glycosylated chemical combination Thing can show certain effect on physiology and pathology.Such as: the 2,2 '-F-araAs similar to adenine structure are killing Efficient activity can be shown on evil protozoon parasite；It is special that glycosylated indole ring also can show it on human cancer Different pharmacologically active, being based on glycosylated indole has a pharmacologically active being so conducive to the mankind, and Zhao Yu sweet smell academician seminar exists Within 2014, achieve synthesis glycosylated benzazolyl compounds (Zhang, F. by the method for organic synthesis；Mu,D.；Wang,L.；Du, P.；Han,F.；Zhao,Y.The Journal of organic chemistry 2014,79,9490).Explore this kind of glycosylated jeterocyclic chemistry The synthesis of compound and using value thereof, have been subjected to the concern of increasing scientific research personnel.Through consulting substantial amounts of document, I Note that synthesis report few of condensed hetero ring in quinazoline derivant quinazoline compounds, especially pyrazolo [1,5-c] Quinazoline compounds synthesis aspect, and glycosylated pyrazolo [1,5-c] quinazoline compound did not also have been reported that.Therefore, knot Close our seminar in recent years to the synthetic method of pyrazolo [1,5-c] quinazoline compounds and the research of pharmacologically active and achievement, And the application prospect of glycosylated heterocyclic compound, enter synthesizing a kind of glycosyl modified pyrazolo [1,5-c] quinazoline compound Gone the research of exploration, and achieved well progress, invented and a kind of had no what document was reported, prepared by novel method Glycosylated pyrazolo [1,5-c] quinazoline compounds.The catalyst of this reaction is the most economical, and side reaction is less, and post processing Convenient, fast.
Summary of the invention
It is an object of the invention to provide a kind of acquisition convenient and swift, efficient glycosylated pyrazolo [1,5-c] quinazoline compounds Preparation method.
The present invention be various aldose 3 under the catalysis of sulfamic acid, and make solvent with acetic anhydride, obtain acetyl group at 60 DEG C complete Sugar 4 (the Zeng Hongyao of protection；Liao Liangcong；Wang Yinghong；Sun Guofeng；Recklessly educate Guangdong chemical industry 2013,1,30), subsequently dry In dry dichloromethane, add boron trifluoride ether solution and propilolic alcohol, react under room temperature and obtain the end group of full acetyl protection Alkynes sugar 1 (Yin, X.；Liu,C.；Zhuo,S.；Xu,Y.；Zhang, B.Dalton transactions 2015,44,1526.), Quan Yi End-group alkyne sugar 1 and the quinazoline N of acyl protection, N-dipolar compound, under the protection of nitrogen, uses Ag2O makees catalyst, and DBU makees Alkali, has synthesized glycosylated pyrazolo [1,5-c] quinazoline compounds 2. efficiently at 70 DEG C
1,3-dipolar compound A containing quinazoline skeleton synthesized with the inventor of this patent is sugared with the end-group alkyne of full acetyl protection (1) compound 2 is obtained by 1,3-dipole-diople interaction.
The reaction equation that 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound is prepared in described silver catalysis is:
It is quinazoline N, N-dipolar compound shown in reaction equation Chinese style A, the various end-group alkynes protected by acetyl group shown in 1 in formula Sugar compounds, is 2-glycosyl substituted pyrazolo [1,5-c] quinazoline compounds shown in 2 in formula, and Ts is to Methyl benzenesulfonyl base. Specifically comprise the following steps that
(1) end-group alkyne sugar (1) that the step synthesis in document is full acetylated is pressed；
(2) in clean reaction tube, the N, N-dipolar compound (A) (0.24mmol, 1.2equiv.) containing quinazoline skeleton is added Full acetylated end-group alkyne sugar (1) (0.2mmol, 1.0equiv.) and catalyst Ag with solid-state2O (0.016mmol), N2In the environment of add alkali DBU (0.4mmol) and solvent NMP (2mL), reaction 0.5 3h, TLC point plate of heating is supervised Survey；
(3), after reaction terminates, reactant liquor is concentrated by 3 extractions, organic layer and is obtained pure glycosylated pyrrole through column chromatography Azoles also [1,5-c] quinazoline framework compound 2.
The optimum condition of the present invention:
(1) Ag that catalyst is 8mol% used in reaction system2O；
(2) in reaction system, the consumption of alkali is 2equiv.；
(3) reaction temperature is 70 DEG C.
Beneficial effects of the present invention: the inventive method reaction condition is gentle, and cheaper starting materials is easy to get, and cost is relatively low, and side reaction is few, just In separating-purifying, simple to operate, and wide application range of substrates (R is H or-OCH3Deng electron-donating group ,-Br or Cl Deng electron withdraw group；Sugar is the various glycosyls protected by acetyl group), there is considerable application prospect.
Detailed description of the invention
Example 1
Unsubstituted quinazoline N, the N-dipolar compound and 0.2 of 0.24mmol is added in the Schlenk pipe of clean 25mL The full acetyl Fructus Vitis viniferae end-group alkyne sugar of the solid-state of mmol, and the catalyst Ag of 0.016mmol2O, nitrogen protection adds at room temperature Enter the solvent NMP of alkali DBU and 2mL of 0.4mmol, reaction is placed in the reactive tank of 70 DEG C reaction 2h, TLC with Completely, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate after terminating and extracts 3 times by reaction, merges in track monitoring reaction Organic facies is also dried with anhydrous sodium sulfate, and organic facies obtains pure 2-(2,3,4,6-tetra--O-through filtration, concentration column chromatography again Acetyl group-α-D-) glucosyl group pyrazolo [1,5-c] quinazoline 2a.White solid, yield is 82%, m.p.:83 84 DEG C.1H NMR(400MHz,CDCl3) δ 8.96 (s, 1H), 7.90 (dd, J=18.6,7.9Hz, 2H), 7.56 (dt, J=26.0,7.3 Hz, 2H), 6.88 (s, 1H), 5.28 4.97 (m, 4H), 4.85 (d, J=12.9Hz, 1H), 4.65 (d, J=7.8Hz, 1H), 4.24 (dd, J=12.2,4.5Hz, 1H), 4.11 (d, J=10.7Hz, 1H), 3.69 (d, J=9.4Hz, 1H), 2.05 1.86 (m, 12H).
13C NMR(100MHz,CDCl3)δ170.6,170.2,169.4,169.2,154.0,139.7,139.6,139.0,130.0,128.8, 128.3,123.2,119.9,99.8,97.5,72.8,72.0,71.3,68.3,64.8,61.9,53.4,20.7,20.7,20.6.
HRMS(ESI)[M+Na]+m/z calcd for C25H27N3NaO10 552.1594,found 552.1600.
Example 2
6,7-dimethoxy substituted quinazoline N, the N-dipole of 0.24mmol is added in the Schlenk pipe of clean 25mL The full acetyl Fructus Vitis viniferae end-group alkyne sugar of the solid-state of compound and 0.2mmol, and the catalyst Ag of 0.016mmol2O, nitrogen is protected Protect the solvent NMP of alkali DBU and 2mL adding 0.4mmol at room temperature, reaction is placed in the reactive tank of 70 DEG C anti- Answer the reaction of 0.5h, TLC tracking and monitoring completely, react and after terminating, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate Extracting 3 times, merge organic facies and be dried with anhydrous sodium sulfate, organic facies obtains pure 8,9-through filtration, concentration column chromatography again Dimethoxy-2-(2,3,4,6-tetra--O-acetyl group-α-D-) glucosyl group pyrazolo [1,5-c] quinazoline 2b.White solid, yield It is 85%, m.p.:112 113 DEG C.
1H NMR(400MHz,CDCl3)δ8.97(s,1H),7.36(s,1H),7.29(s,1H),6.82(s,1H),5.29–5.04 (m, 4H), 4.93 (d, J=12.8Hz, 1H), 4.75 (d, J=7.8Hz, 1H), 4.32 (dd, J=12.3,4.6Hz, 1H), 4.20 (d, J=10.5Hz, 1H), 4.05 (s, 3H), 4.02 (s, 3H), 3.79 (d, J=5.2Hz, 1H), 2.12 1.97 (m, 12H).13C NMR(100MHz,CDCl3)δ170.6,170.2,169.4,169.3,153.8,151.4,150.1,139.6,137.5,135.1, 113.7,109.4,102.9,99.9,95.8,72.8,71.9,71.3,68.3,65.0,61.9,56.3,56.2,20.7,20.6,20.6.
HRMS(ESI)[M+Na]+m/z calcd for C27H31N3O12 612.1805,found 612.1813.
Example 3
Add in the Schlenk pipe of clean 25mL 0.24mmol 6-chlorine substituted quinazoline N, N-dipolar compound and The full acetyl Fructus Vitis viniferae end-group alkyne sugar of the solid-state of 0.2mmol, and the catalyst Ag of 0.016mmol2O, nitrogen is protected in room temperature The solvent NMP of alkali DBU and 2mL of lower addition 0.4mmol, is placed in the reactive tank of 70 DEG C reaction 2.5h by reaction, Completely, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate after terminating and extracts 3 times the reaction of TLC tracking and monitoring by reaction, Merging organic facies and be dried with anhydrous sodium sulfate, organic facies obtains the chloro-2-of pure 9-(2,3,4,6-through filtration, concentration column chromatography again Four-O-acetyl group-α-D-) glucosyl group pyrazolo [1,5-c] quinazoline 2c.Faint yellow solid, yield is 47%, m.p.:91 92℃。
1H NMR(400MHz,CDCl3) δ 9.01 (s, 1H), 7.97 (s, 1H), 7.88 (d, J=8.6Hz, 1H), 7.60 (d, J=7.0 Hz, 1H), 6.97 (s, 1H), 5.25-5.07 (m, 4H), 4.93 (d, J=12.9Hz, 1H), 4.72 (d, J=7.8Hz, 1H), 4.31 (dd, J=12.2,4.6Hz, 1H), 4.20 (d, J=12.4Hz, 1H), 3.77 (d, J=11.4Hz, 1H), 2.10 2.01 (m,12H).
13C NMR(100MHz,CDCl3)δ170.7,170.2,169.4,169.3,154.3,139.1,138.6,138.1,134.1,130.4, 130.3,122.7,121.0,99.9,98.1,72.8,72.0,71.2,68.3,64.7,61.9,20.7,20.6.
HRMS(ESI)[M+Na]+m/z calcd for C25H26ClN3O10 586.1204,found 586.1206.
Example 4
Unsubstituted quinazoline N, the N-dipolar compound and 0.2 of 0.24mmol is added in the Schlenk pipe of clean 25mL The full acetylated mannan end-group alkyne sugar of the solid-state of mmol, and the catalyst Ag of 0.016mmol2O, nitrogen protection adds at room temperature Enter the solvent NMP of alkali DBU and 2mL of 0.4mmol, reaction is placed in the reactive tank of 70 DEG C reaction 1.5h, TLC Completely, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate after terminating and extracts 3 times by reaction, closes in tracking and monitoring reaction And organic facies being dried with anhydrous sodium sulfate, organic facies is again through filtering, concentrate and column chromatography obtaining pure 2-(2,3,4,6-tetra--O- Acetyl group-α-D-) mannose group pyrazolo [1,5-c] quinazoline 2d.Colourless oil liquid, yield is 92%.
1H NMR(400MHz,CDCl3) δ 9.05 (s, 1H), 8.05 (d, J=7.7Hz, 1H), 7.96 (d, J=8.0Hz, 1H), 7.68 (t, J=7.5Hz, 1H), 7.62 (t, J=7.4Hz, 1H), 7.03 (s, 1H), 5.43 (d, J=10.2Hz, 1H), 5.36 5.31 (m, 2H), 5.03 (s, 1H), 4.98 (d, J=12.6Hz, 1H), 4.85 (d, J=12.6Hz, 1H), 4.33 (dd, J=12.4,5.0Hz, 1H), 4.14 (t, J=11.0Hz, 2H), 2.16 (s, 3H), 2.13 (s, 3H), 2.05 (s, 3H), 2.01 (s, 3H).
13C NMR(100MHz,CDCl3)δ170.7,170.0,169.9,169.7,153.3,139.8,139.6,139.0,130.0,128.7, 128.3,123.4,119.9,97.7,97.0,69.5,69.0,68.9,66.1,63.2,62.4,20.9,20.8,20.7,20.7.
HRMS(ESI)[M+Na]+m/z calcd for C25H27N3O10 552.1594,found 552.1590.
Example 5
6,7-dimethoxy substituted quinazoline N, the N-dipole of 0.24mmol is added in the Schlenk pipe of clean 25mL The full acetylated mannan end-group alkyne sugar of the solid-state of compound and 0.2mmol, and the catalyst Ag of 0.016mmol2O, nitrogen is protected Protect the solvent NMP of alkali DBU and 2mL adding 0.4mmol at room temperature, reaction is placed in the reactive tank of 70 DEG C anti- Answer the reaction of 1.5h, TLC tracking and monitoring completely, react and after terminating, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate Extracting 3 times, merge organic facies and be dried with anhydrous sodium sulfate, organic facies obtains pure 8,9-through filtration, concentration column chromatography again Dimethoxy-2-(2,3,4,6-tetra--O-acetyl group-α-D-) mannose group pyrazolo [1,5-c] quinazoline 2e.White solid, yield It is 71%, m.p.:83 84 DEG C.
1H NMR(400MHz,CDCl3) δ 8.99 (s, 1H), 7.38 (s, 1H), 7.35 (s, 1H), 6.90 (s, 1H), 5.42 (d, J=9.9 Hz, 1H), 5.36 5.31 (m, 2H), 5.01 4.96 (m, 2H), 4.83 (d, J=12.6Hz, 1H), 4.33 (d, J=11.8Hz, 1H), 4.15 (d, J=13.0Hz, 2H), 4.09 (s, 3H), 4.03 (s, 3H), 2.16 (s, 3H), 2.13 (s, 3H), 2.05 (s, 3H), 2.01(s,3H).
13C NMR(100MHz,CDCl3)δ170.7,170.0,170.0,169.7,153.2,151.5,150.2,139.8,137.6, 135.1,113.7,109.4,103.2,97.0,96.0,69.5,69.1,68.9,66.1,63.4,62.4,56.4,56.2,20.8,20.7,20.7. HRMS(ESI)[M+Na]+m/z calcd for C27H31N3NaO12 612.1805,found 612.1807.
Example 6
Add in the Schlenk pipe of clean 25mL 0.24mmol 6-bromine substituted quinazoline N, N-dipolar compound and The full acetylated mannan end-group alkyne sugar of the solid-state of 0.2mmol, and the catalyst Ag of 0.016mmol2O, nitrogen is protected in room temperature The solvent NMP of alkali DBU and 2mL of lower addition 0.4mmol, is placed in the reactive tank of 70 DEG C reaction 3h, TLC by reaction Completely, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate after terminating and extracts 3 times by reaction, closes in tracking and monitoring reaction And organic facies being dried with anhydrous sodium sulfate, organic facies is again through filtering, concentrate and column chromatography obtaining the bromo-2-of pure 9-(2,3,4,6- Four-O-acetyl group-α-D-) mannose group pyrazolo [1,5-c] quinazoline 2f.Yellow solid, yield is 51%, m.p.:73 75 DEG C.1H NMR(400MHz,CDCl3) δ 9.04 (s, 1H), 8.20 (d, J=1.7Hz, 1H), 7.83 (d, J=8.7Hz, 1H), 7.76 (dd, J=8.7,1.7Hz, 1H), 7.04 (s, 1H), 5.42 (dd, J=10.3,3.1Hz, 1H), 5.36 5.31 (m, 2H), 5.03 4.94 (m, 2H), 4.84 (d, J=12.6Hz, 1H), 4.33 (dd, J=12.6,5.1Hz, 1H), 4.16 4.09 (m, 2H), 2.16 (s,3H),2.13(s,3H),2.05(s,3H),2.01(s,3H).13C NMR(101MHz,CDCl3)δ170.7,170.1,170.0, 169.7,153.6,139.3,138.6,138.4,133.2,130.4,126.0 122.1,121.4,98.3,97.0,77.2,69.4,69.0, 68.9,66.1,63.2,62.4,20.9,20.8,20.7,20.71.
HRMS(ESI)[M+Na]+m/z calcd for C25H26BrN3NaO10 630.0699,found 630.0698.
Example 7
Unsubstituted quinazoline N, the N-dipolar compound and 0.2 of 0.24mmol is added in the Schlenk pipe of clean 25mL The thick full acetyl gala end-group alkyne sugar of mmol, and the catalyst Ag of 0.016mmol2O, nitrogen is protected at room temperature Add the solvent NMP of alkali DBU and 2mL of 0.4mmol, reaction is placed in the reactive tank of 70 DEG C reaction 2h, TLC Completely, reactant liquor is cooled to room temperature, reactant liquor water and ethyl acetate after terminating and extracts 3 times by reaction, closes in tracking and monitoring reaction And organic facies being dried with anhydrous sodium sulfate, organic facies is again through filtering, concentrate and column chromatography obtaining pure 2-(2,3,4,6-tetra--O- Acetyl group-α-D-) galactosyl pyrazolo [1,5-c] quinazoline 2g.White solid, yield is 89%, m.p.:79 80 DEG C.1H NMR(400MHz,CDCl3) δ 9.06 (s, 1H), 8.04 (dd, J=7.8,1.2Hz, 1H), 7.98 7.93 (m, 1H), (7.69 td, J=7.3,1.4Hz, 1H), 7.65 7.59 (m, 1H), 7.04 (s, 1H), 5.43 5.38 (m, 1H), 5.23 (s, 1H), 5.18 (d, J=1.8Hz, 1H), 5.06 (dd, J=6.0,1.7Hz, 1H), 4.98 (d, J=12.8Hz, 1H), 4.85 (d, J=12.8 Hz,1H),4.39–4.35(m,2H),4.27–4.22(m,1H),2.15(s,3H),2.11(s,3H),2.10(s,3H),2.07(s, 3H).
13C NMR(100 MHz,CDCl3)δ170.6,170.1,170.0,169.7,154.1,139.8,139.6,139.1,130.0,128.8, 128.3,123.4,119.9,105.1,97.7,81.5,80.3,69.3,63.0,62.6,20.9,20.8,20.7,20.7.
HRMS(ESI)[M+Na]+m/z calcd for C25H27N3NaO10 552.1594,found 552.1597.

Claims (4)

1. silver is catalyzed the method preparing 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound, it is characterised in that:
(1) reaction equation that 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound is prepared in described silver catalysis is:
Formula is quinazoline N shown in A, N-dipolar compound, the various end-group alkyne sugar compounds protected by acetyl group shown in 1 in formula, 2 institute in formula Showing it is 2-glycosyl substituted pyrazolo [1,5-c] quinazoline compounds, Ts is to Methyl benzenesulfonyl base:
(2) described silver is catalyzed and prepares concretely comprising the following steps of 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound:
A () presses end-group alkyne sugar (1) that the step synthesis in document is full acetylated；
(b) add in clean reaction tube 24mmol, 1.2equiv. containing quinazoline skeleton N, N-dipolar compound (A), solid-state Full acetylated end-group alkyne sugar (1) and the catalyst Ag of 0.016mmol of 0.2mmol, 1.0equiv.2O, at N2Environment The solvent NMP of alkali DBU and 2mL of lower addition 0.4mmol, reaction 0.5 3h, TLC point plate monitoring of heating；
C () reaction terminates after, reactant liquor is concentrated by 3 extractions, organic layer and is obtained pure glycosylated pyrrole through column chromatography Azoles also [1,5-c] quinazoline framework compound 2.
The method that 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound is prepared in silver catalysis the most according to claim 1, its feature exists In: the Ag that catalyst is 8mol% used in described reaction system2O。
The method that 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound is prepared in silver catalysis the most according to claim 1, its feature exists In: in described reaction system, the consumption of alkali is 2equiv..
The method that 2-glycosyl substituted pyrazolo [1,5-c] quinazoline framework compound is prepared in silver catalysis the most according to claim 1, It is characterized in that: described reaction temperature is 70 DEG C.
CN201610343687.8A 2016-05-22 2016-05-22 Method for preparing 2-glycosyl substituted pyrazol[1,5-c]quinazoline framework compound through silver catalysis Pending CN105924483A (en)

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CN104610267A (en) * 2015-02-09 2015-05-13 江西师范大学 Method for efficiently synthetizing 6-alkylpyrazol-[1,5-c]-quinazoline skeleton compounds under no catalytic condition

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