CN1053186C - Quinolinoxazole compound - Google Patents
Quinolinoxazole compound Download PDFInfo
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- CN1053186C CN1053186C CN98110943A CN98110943A CN1053186C CN 1053186 C CN1053186 C CN 1053186C CN 98110943 A CN98110943 A CN 98110943A CN 98110943 A CN98110943 A CN 98110943A CN 1053186 C CN1053186 C CN 1053186C
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- compound
- quinoline
- oxazoline
- quinolinoxazole
- phenyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 239000000126 substance Substances 0.000 claims description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 230000006340 racemization Effects 0.000 claims 1
- -1 quinoline oxazoline compound Chemical class 0.000 abstract description 11
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001414 amino alcohols Chemical class 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 2
- 238000005888 cyclopropanation reaction Methods 0.000 abstract 2
- 230000003287 optical effect Effects 0.000 abstract 2
- BSCXJHRXVLREBO-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazole;quinoline Chemical class C1CN=CO1.N1=CC=CC2=CC=CC=C21 BSCXJHRXVLREBO-UHFFFAOYSA-N 0.000 abstract 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002918 oxazolines Chemical class 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- VERUITIRUQLVOC-UHFFFAOYSA-N 2-butyl-4,5-dihydro-1,3-oxazole Chemical group CCCCC1=NCCO1 VERUITIRUQLVOC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- WOMOPYCBDBRBQI-UHFFFAOYSA-N formyl chloride quinoline Chemical compound C(=O)Cl.N1=CC=CC2=CC=CC=C12 WOMOPYCBDBRBQI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- JBULSURVMXPBNA-YFKPBYRVSA-N (2r)-2-amino-3,3-dimethylbutan-1-ol Chemical class CC(C)(C)[C@@H](N)CO JBULSURVMXPBNA-YFKPBYRVSA-N 0.000 description 1
- JBULSURVMXPBNA-RXMQYKEDSA-N (2s)-2-amino-3,3-dimethylbutan-1-ol Chemical class CC(C)(C)[C@H](N)CO JBULSURVMXPBNA-RXMQYKEDSA-N 0.000 description 1
- FCOPZNOYFMGOEO-UHFFFAOYSA-N C(CCC)O.NC1C(C(=O)O)=CC=CC1(C(=O)O)C Chemical class C(CCC)O.NC1C(C(=O)O)=CC=CC1(C(=O)O)C FCOPZNOYFMGOEO-UHFFFAOYSA-N 0.000 description 1
- FCOPZNOYFMGOEO-NNVMMKAESA-N C(CCC)O.N[C@@H]1C(C(=O)O)=CC=CC1(C(=O)O)C Chemical class C(CCC)O.N[C@@H]1C(C(=O)O)=CC=CC1(C(=O)O)C FCOPZNOYFMGOEO-NNVMMKAESA-N 0.000 description 1
- FCOPZNOYFMGOEO-CZRNMOARSA-N C(CCC)O.N[C@H]1C(C(=O)O)=CC=CC1(C(=O)O)C Chemical class C(CCC)O.N[C@H]1C(C(=O)O)=CC=CC1(C(=O)O)C FCOPZNOYFMGOEO-CZRNMOARSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000012773 agricultural material Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
Abstract
本发明属于有机合成领域，涉及一类喹啉唑啉化合物。The invention belongs to the field of organic synthesis and relates to a class of quinoline-oxazoline compounds.
本发明以8-喹啉羧酸为原料与氨基醇进行反应，生成本发明所说的喹啉唑啉化合物。该喹啉唑啉化合物在4位上有一个手性中心，因此该所说的化合物有两个旋光异构体；右旋喹啉唑啉化合物和左旋喹啉唑啉化合物，该两个旋光异构体的等量混合物则成为外消旋喹淋唑啉。本发明所说的喹啉唑啉化合物是一种用途十分广泛的化合物，如可作为手性配体用于不对称环丙烷化反应，对该环丙烷化反应具有较高的立体选择性，e.e.值可达到50%以上。The present invention uses 8-quinoline carboxylic acid as a raw material to react with amino alcohol to generate the quinoline oxazoline compound of the present invention. The quinoline-oxazoline compound has a chiral center at the 4-position, so the said compound has two optical isomers; An equal mixture of two optical isomers becomes racemic quinazoline. Said quinoline oxazoline compound of the present invention is a kind of very extensive compound of purposes, as can be used for asymmetric cyclopropanation reaction as chiral ligand, this cyclopropanation reaction has higher stereoselectivity, The e.e. value can reach more than 50%.
Description
The invention belongs to the organic synthesis field, relate to a class Quinolinoxazole compound.
Oxazoline and to have substituent compound be a kind of important organic intermediate all has in fields such as dyestuff, medicine, agricultural chemicals and materials very to use widely.In recent years, many patent disclosures have various substituting group De oxazoline compounds, for example:
(1) U.S.Patents 2,870, and 159,2,870,160,2,870,161,2,883,410 disclose 2 bit amino substituting group De oxazoline compounds respectively, and this compound has obtained important use in medicine is synthetic;
(2) U.S.Patents 2,865, and 856,2,911,419,2,964,471,2,924,571, disclose 2 heterocyclic substituent De oxazoline compounds respectively, this compound has obtained important use in the preparation of impregnating material;
(3) Henri Brunner is at " Catalyic Asymmetric Synthesis " Iwao Ojima Ed, VCH Publishers, reported the oxazoline compounds that 2-position pyridine replaces in 1993, this compounds has obtained important use in organic synthesis.
Along with industrial fast development, branch of industry needs the departments of science and technology constantly to research and develop Xin De oxazoline compounds, to satisfy the needs of organic synthesis industry.
The objective of the invention is to disclose a kind of Quinolinoxazole compounds.
Design of the present invention is such:
With the 8-Quinoline Carboxylic Acid is that raw material and amino alcohol react, and generates the said Quinolinoxazole compound of the present invention; When adopting the amino alcohol of different structure, can obtain the Quinolinoxazole compound of different structure.
The said Quinolinoxazole of the present invention is the compound with following chemical structure of general formula:
In the formula:
R
1Be H, Me, Et, i-Pr, i-Bu, t-Bu, Ph or PhCH
2In one;
R
2Be H, Me, Et, i-Pr, i-Bu, t-Bu, Ph or PhCH
2In one;
R
3Be one among H, Me, Et, i-Pr, i-Bu, the Ph;
X is among H, Me, t-Bu, Ph or the MeO;
n＝1～3；
R
1, R
2, R
3Can be identical, also can be different.
Said Quinolinoxazole compound, on 4, there is a chiral centre, so have two optically active isomers, one is the dextrorotation Quinolinoxazole compound---(4R)-Quinolinoxazoles, it two is left-handed Quinolinoxazole compound---(4S)-Quinolinoxazoles, and the equal amount of mixture of these two optically active isomers then becomes racemic modification---(±)-Quinolinoxazoles.Therefore, in fact the said Quinolinoxazole compound of the present invention comprises racemic modification, dextrorotatory form and levo form.Racemic modification, dextrorotatory form and levo form all have identical chemical structure of general formula, but have different three-dimensional arrangements and rotary light performance.
The said compound of the present invention can synthesize by following method:
With reaction raw materials 8-Quinoline Carboxylic Acid and thionyl chloride by 1: the weight ratio of (10～15) places reactor, reflux 10～20 hours, reaction solution is removed excessive thionyl chloride and is obtained quinoline formyl chlorine.The quinoline formyl chlorine of gained is dissolved in the chloroform, the amino alcohol that under-10 ℃ condition, adds 0.8～1.2 times (mol ratio), drip the trolamine of 3 times (weight ratios) again, reacted 20～30 hours down at 25 ℃, reaction solution obtains crude product through washing and drying except that after desolvating, obtain amide compound through silica gel column chromatography again, productive rate 60～85% (calculating) by 8-Quinoline Carboxylic Acid, amide compound is dissolved in the chloroform, 25 ℃ of thionyl chlorides that drip 2～3 times (weight ratios) down, refluxed 1 hour, through washing and drying remove desolvate after again through silica gel column chromatography, obtain pure chloro-product, chloro thing and sodium hydroxide refluxed in methyl alcohol 10～20 hours, the reaction solution chloroform extraction, extraction liquid is through washing, dry back is removed and is desolvated, and thick product obtains pure Quinolinoxazole compound with recrystallization or silica gel column chromatography.Reaction process is shown below:
R
1, R
2, R
3, X and n be same as above.
The said Quinolinoxazole compound of the present invention is a kind of purposes compound very widely, for example can be used as chiral ligand and is used for asymmetric cyclopropanization reaction, and its reaction formula is:
In the formula: L
*=(4S)-2-(8 '-quinoline)-4-benzyl-2-oxazoline
Because the complex compound that said Quinolinoxazole compound of the present invention and copper form has suitable configuration, therefore this cyclopropanization reaction had higher stereoselectivity, e.e. value reaches more than 50%, and corresponding Bi Ding oxazoline chiral ligand does not then have stereoselectivity to this reaction.
To be further elaborated the said compound of the present invention by embodiment below.
Embodiment 1
(±)-2-(8 '-quinoline)-4-phenyl-2-oxazoline, its chemical structural formula is as follows:
This compound process is as follows:
3.46 gram 8-Quinoline Carboxylic Acids and 29ml thionyl chlorides are placed have stirring, in the reactor of heating and reflux, reflux 8 hours, excessive thionyl chloride is removed in distillation, resulting 8-quinoline formyl chlorine dissolves with the 50ml chloroform, add 2.88 gram (±)-2-phenyl-2-monoethanolamines down at-10 ℃, drip the 14ml triethylamine again, be warming up to 25 ℃, restir 24 hours, reaction solution is water respectively, 5% sodium hydrogen carbonate solution and saturated common salt water washing, anhydrous sodium sulfate drying, rotary evaporation removes the back resistates that desolvates through silica gel column chromatography (eluent is ethyl acetate/petroleum ether 1: 1), obtains white solid amide compound 4.30 grams, and productive rate is 69%; These compound 3.83 grams are dissolved in the 100ml chloroform, drip the 4.8ml thionyl chloride down at 25 ℃, adding the back refluxed 1 hour, be cooled to 25 ℃ and add 20ml water, tell organic phase, sodium hydrogen carbonate solution with 5% and saturated common salt water washing, anhydrous sodium sulfate drying, rotary evaporation removes desolvate back resistates and 1.16 gram sodium hydroxide and 150ml methanol mixed, and reflux boiled off methyl alcohol after 15 hours, the saturated common salt water washing of resistates chloroform extraction, extraction liquid, anhydrous sodium sulfate drying, rotatory evaporator removes and desolvates after silica gel column chromatography (eluent is ethyl acetate/petroleum ether 2: 1), obtain white solid (±)-2-(8 '-quinoline)-4-phenyl-2-oxazoline 1.46 grams, productive rate is 40%, and fusing point is 133 ℃.Spectral data is as follows:
1H NMR (CDCl
3): δ (ppm) 4.45 (m, 1H), 4.98 (dd, J=8.4,1.7Hz, 1H), 5.58 (dd, J=8.1,2.1Hz, 1H), 7.38 (m, 6H), 7.60 (dd, J=7.8,0.8Hz, 1H), 7.96 (dd, J=6.9,1.3Hz, 1H), 8.22 (m, 2H), 9.11 (dd, J=2.6,1.7 Hz, 1H) IR (KBr compressing tablet): (cm
-1) 1649,1611,1592,1577,495,1472,1454,1387,1353,1320,1292,1277,1250,1191,1126,1011MS:m/e (%) 274 (M
+) (16.7), 244 (57.8), 243 (67.1), 156 (100), 155 (27.5), 128 (22.6), 118 (16.8) ultimate analysis (C
18H
14N
2O): C:78.80, H:5.22, N:10.10
Embodiment 2
(4S)-2-(8 '-quinoline)-4-phenyl-2-oxazoline:
With (±)-2-phenyl-2-monoethanolamine among (S)-2-phenyl-2-monoethanolamine replacement embodiment 1, preparation method, chemical structural formula, spectral data and ultimate analysis are identical with embodiment 1,136 ℃ of fusing points, [α]
20 D=-50 (c0.8, EtOH).
Embodiment 3
(4R)-2-(8 '-quinoline)-4-phenyl-2-oxazoline:
With (±)-2-phenyl-2-monoethanolamine among (R)-2-phenyl-2-monoethanolamine replacement embodiment 1, preparation method, chemical structural formula, spectral data and ultimate analysis are identical with embodiment 1,132 ℃ of fusing points, [α]
20 D=+51 (c0.6, EtOH).
Embodiment 4
(4S)-and 2-(8 '-quinoline)-4-benzyl-2-oxazoline, its chemical structural formula is:
With (±)-2-phenyl-2-monoethanolamine among (S)-3-phenyl-2-amino-1-propyl alcohol replacement embodiment 1, other process is identical with embodiment 1.(4S)-and 2-(8 '-quinoline)-4-benzyl-2-oxazoline is a white solid, fusing point is 96 ℃, [α]
20 D=-8 (c0.8, EtOH); Spectral data is as follows:
1H NMR (CDCl
3): δ (ppm) 2.80 (dd, J=9.0,4.7Hz, 1H), 3.30 (dd, J=8.9,4.8Hz, 1H), 4.22 (dd, J=7.5,0.8Hz, 1H), 4.46 (dd, J=4.5,3.2Hz, 1H), 4.72 (m, 1H), 7.22 (m, 5H), 7.38 (dd, J=4.2,4.2Hz, 1H), 7.49 (dd, J=7.3,1.2Hz, 1H), 7.85 (dd, J=6.9,1.3Hz, 1H), 8.04 (dd, J=5.3,1.2Hz, 1H), 8.11 (dd, J=1.8,6.5Hz, 1H), 9.02 (dd, J=2.5,1.8 Hz, 1H) IR (KBr compressing tablet): (cm
-1) 1656,1612,1602,1592,1578,1494,1471,1451,1389,1367,1356,1303,1286,1258,1194,1138,1072,1017,1005MS:m/e (%) 289 (M
+) (37.8), 198 (88.6), 197 (89.0), 169 (62.7), 155 (70.6), 144 (27.1), 143 (100), 128 (60.8) ultimate analysis (C
19H
16N
2O): C:77.70, H:5.60, N:9.44
Embodiment 5
(4R)-2-(8 '-quinoline)-4-benzyl-2-oxazoline:
With (±)-2-phenyl-2-monoethanolamine among (R)-3-phenyl-2-amino-1-propyl alcohol replacement embodiment 1, other process is identical with embodiment 1.Chemical structural formula, spectral data and ultimate analysis are identical with embodiment 4, and white solid, fusing point are 97 ℃, [α]
20 D=+8.4 (c0.8, EtOH).
Embodiment 6
(±)-2-(8 '-quinoline)-4-methyl-2-oxazoline, its chemical structural formula is:
With (±)-2-phenyl-2-monoethanolamine among (±)-2-amino-1-propyl alcohol replacement embodiment 1, other process is identical with embodiment 1.(±)-2-(8 '-quinoline)-4-methyl-2-oxazoline is a white solid, and fusing point is 114 ℃;
1H NMR (CDCl
3): δ (ppm) 1.46 (dd, J=5.3Hz, 3H), 4.08 (t, J=7.6Hz, 1H), 4.61 (m, 2H), 7.43 (dd, J=4.2,4.1Hz, 1H), 7.56 (m, 1H), 7.91 (dd, J=6.8,1.4Hz, 1H), 8.16 (m, 2H), 9.077 (dd, J=1.8,1.2Hz, 1H), 7.85 (dd, J=6.9,1.3Hz, 1H), 8.04 (dd, J=5.3,1.2Hz, 1H), 8.11 (dd, J=1.8,1.4Hz, 1H) IR (coating): (cm
-1) 1650,1594,1574,1546,1499,1473,1451,1388,1374,1355,1342,1296,1262,1258,1192,1142,1131,1061,1009MS:m/e (%) 212 (M
+) (61.9), 197 (63.8), 181 (24.8), 171 (20.8), 156 (100), 155 (58.7), 154 (27.3), 142 (54.0), 129 (78.5), 128 (45.4) ultimate analysis (C
13H
12N
2O): C:71.77, H:5.96, N:13.24
Embodiment 7
(4S)-2-(8 '-quinoline)-4-methyl-2-oxazoline:
With (±)-2-phenyl-2-monoethanolamine among (S)-2-amino-1-propyl alcohol replacement embodiment 1, other process is identical with embodiment 1.Chemical structural formula, spectral data and ultimate analysis are identical with embodiment 6, and fusing point is 121 ℃, [α]
20 D=-42 (c0.6, EtOH).
Embodiment 8 (±)-2-(8 '-quinoline)-4-sec.-propyl-2-oxazoline, its chemical structural formula is:
With (±)-2-phenyl-2-monoethanolamine among (±)-2-amino-3-methyl isophthalic acid-butanols replacement embodiment 1, other process is identical with embodiment 1.(±)-2-(8 '-quinoline)-4-sec.-propyl-2-oxazoline is an oily matter;
1H NMR (CDCl
3): δ (ppm) 0.97 (dd, J=8.7Hz, 6H), 1.92 (m, 1H), 3.24 (m, 2H), 4.51 (m, 1H), 7.33 (dd, J=4.2,3.5Hz, 1H), 7.46 (m, 1H), 7.80 (dd, J=6.8,1.4Hz, 1H), 8.05 (m, 2H), 8.96 (dd, J=2.4,1.7Hz, 1H) IR (coating): (cm
-1) 1657,1610,1594,1575,1498,1468,1387,13512,1298,1284,1256,1192,1140,1128,1066,1004MS:m/e (%) 197 (82.0), 198 (49.5), 168 (23.80,156 (63.6), 155 (42.1), 144 (15.1), 143 (100), 128 (48.8) ultimate analysis (C
15H
16N
2O): C:73.19, H:6.74, N:11.73
Embodiment 9
(4S)-2-(8 '-quinoline)-4-sec.-propyl-2-oxazoline:
With (±)-2-phenyl-2-monoethanolamine among (S)-2-amino-3-methyl isophthalic acid-butanols replacement embodiment 1, other process is identical with embodiment 1.Chemical structural formula, spectral data and ultimate analysis are identical with embodiment 8, oily matter, [α]
20 D=-59 (c0.9, EtOH).
Embodiment 10
(4R)-2-(8 '-quinoline)-4-sec.-propyl-2-oxazoline:
With (±)-2-phenyl-2-monoethanolamine among (R)-2-amino-3-methyl isophthalic acid-butanols replacement embodiment 1, other process is identical with embodiment 1.Chemical structural formula, spectral data and ultimate analysis are identical with embodiment 8, oily matter, [α]
20 D=+57.5 (c0.9, EtOH).
Embodiment 11 (4S)-2-(8 '-quinoline)-4-tertiary butyl-oxazolines, its chemical structural formula is:
With (S)-2-amino-3,3-dimethyl-1-butanols replaces (±)-2-phenyl-2-monoethanolamine among the embodiment 1, and other process is identical with embodiment 1.Oily matter, [α]
20 D=-72 (c1.0, EtOH).
1H NMR (CDCl
3): δ (ppm) 1.05 (s, 9H), 4.20 (m, 1H), 4.39 (t, J=8.3Hz, 1H), 4.61 (m, 1H), 7.42 (dd, J=4.2,4.1Hz, 1H), 7.66 (dd, J=7.2,1.0Hz, 1H), 7.90 (dd, J=6.7,1.5Hz, 1H), 8.08 (dd, J=5.6,1.5Hz, 1H), 8.16 (dd, J=6.5,1.8Hz, 1H), 9.03 (dd, J=2.4,1.8Hz, 1H) IR (coating): (cm
-1) 1656,1610,1594,1574,1550,1499,1478,1393,1354,1399,1297,1260,1208,1192,1139,1129,1066,1046,1012MS:m/e (%) 256 (M
+ 2) (37.7), 254 (M
+) (100), 197 (84.8), 196 (11.8), 169 (31.5), 156 (29.9), 14 (35.9) ultimate analysis (C
16H
18N
2O): C:78.33, H:7.83, N:12.01
Embodiment 12
(4R)-2-(8 '-quinoline)-4-tertiary butyl-2-oxazoline:
With (R)-2-amino-3,3-dimethyl-1-butanols replaces (±)-2-phenyl-2-monoethanolamine among the embodiment 1, and other process is identical with embodiment 1.Chemical structural formula, spectral data and ultimate analysis are identical with embodiment 11, oily matter, [α]
20 D=+73.8 (c1.0, EtOH).
Claims (4)
1. Quinolinoxazole compound is characterized in that having following chemical structure of general formula:
In the formula:
R
1Be H, Me, Et, i-Pr, i-Bu, t-Bu, Ph or PhCH
2In one;
R
2Be H, Me, Et, i-Pr, i-Bu, t-Bu, Ph or PhCH
2In one;
R
3Be one among H, Me, Et, i-Pr, i-Bu, the Ph;
X is among H, Me, t-Bu, Ph or the MeO;
n＝1～3；
R
1, R
2, R
3Can be identical, also can be different.
2. compound as claimed in claim 1 is characterized in that-Quinolinoxazoles for a kind of racemization Quinolinoxazole compound-(±).
3. compound as claimed in claim 1 is characterized in that being-Quinolinoxazoles of a kind of dextrorotation Quinolinoxazole compound-(4R).
4. compound as claimed in claim 1 is characterized in that being-Quinolinoxazoles of a kind of left-handed Quinolinoxazole compound-(4S).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98110943A CN1053186C (en) | 1998-07-09 | 1998-07-09 | Quinolinoxazole compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98110943A CN1053186C (en) | 1998-07-09 | 1998-07-09 | Quinolinoxazole compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1201793A CN1201793A (en) | 1998-12-16 |
| CN1053186C true CN1053186C (en) | 2000-06-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98110943A Expired - Fee Related CN1053186C (en) | 1998-07-09 | 1998-07-09 | Quinolinoxazole compound |
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| Country | Link |
|---|---|
| CN (1) | CN1053186C (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108774216A (en) * | 2018-02-11 | 2018-11-09 | 尚谷科技（天津）有限公司 | A kind of list tooth Pei Wei oxazoline ligands and its preparation method and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6145169A (en) * | 1984-08-06 | 1986-03-05 | Aisin Warner Ltd | Automatic speed change gear case for car |
| EP0612743A1 (en) * | 1993-02-26 | 1994-08-31 | Takeda Chemical Industries, Ltd. | Oxazolidinedione derivatives, their production and use in lowering blood sugar and lipid levels |
-
1998
- 1998-07-09 CN CN98110943A patent/CN1053186C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6145169A (en) * | 1984-08-06 | 1986-03-05 | Aisin Warner Ltd | Automatic speed change gear case for car |
| EP0612743A1 (en) * | 1993-02-26 | 1994-08-31 | Takeda Chemical Industries, Ltd. | Oxazolidinedione derivatives, their production and use in lowering blood sugar and lipid levels |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1201793A (en) | 1998-12-16 |
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