CN103694189A - Synthesis method of 2-oxazole or 2-thiazole - Google Patents
Synthesis method of 2-oxazole or 2-thiazole Download PDFInfo
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- CN103694189A CN103694189A CN201310709370.8A CN201310709370A CN103694189A CN 103694189 A CN103694189 A CN 103694189A CN 201310709370 A CN201310709370 A CN 201310709370A CN 103694189 A CN103694189 A CN 103694189A
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- thiazole
- oxazole
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention provides a method for synthesizing 2-oxazole or 2-thiazole. The method comprises the following steps: synthesizing a 2-oxazole or 2-thiazole intermediate by taking aromaticnitrile and ethanolamine or cysteamine hydrochloride as raw materials and taking copper acetate as a catalyst; and synthesizing the 2-oxazole or 2-thiazole with a one-pot method by taking DDQ (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone ) as an oxidant. The method has the advantages of mild reaction conditions, easiness in operating, wide range of applicable substrates, high yield and wide application prospect.
Description
Technical field
The synthetic method that the present invention relates to a kind of 2-oxazole or 2-thiazole, belongs to technical field of organic chemistry.
Background technology
In recent years, 2-oxazole or 2-thiazole, because of its unique biological activity, have been subject to paying close attention to widely.Research discovery, 2-oxazole or 2-thiazole are extensively present in natural product, organic dye and medicine as important structural unit.Just because of this, aspect 2-oxazole or 2-thiazole, chemiluminescent polypeptide synthetic in the design of biomolecules, polymeric chemical, drug discovery, there is unrivaled advantage and irreplaceable status.How effectively synthetic 2-thiazole or 2-oxazole become a very important problem.
At present, the method for synthetic 2-oxazole or 2-thiazole mainly contains cyclisation method, coupled method and oxidation style.Prior art exists the 2-oxazole of following shortcoming and defect, particularly C-4, C-5 position unsubstituted and the synthetic of 2-thiazole also there is no practicable method, and this has restricted the application of the important heterogeneous ring compound of this class to a great extent.Therefore the synthetic method of, developing a kind of more effectively 2-oxazole and 2-thiazole has important theory significance and wide application prospect.
Summary of the invention
The object of this invention is to provide a kind of synthetic easy, productive rate is high, the novel method of eco-friendly synthetic 2-oxazole or 2-thiazole.
Implementation procedure of the present invention is as follows:
A synthetic method for 2-oxazole or 2-thiazole, take following synthetic route:
X is S or O, and R is aryl, substituted aryl or heterocyclic radical; Described substituted aryl is C
1～C
5alkyl, halogen radical, amino, cyano group, nitro, the aryl that thiazolyl, oxazolyl replaces; Described heterocyclic radical is pyridyl, thienyl, pyrimidyl or pyrazinyl.
Concrete synthetic method is:
(1) under condition of no solvent, R-CN to be reacted under catalyst acetic acid copper exists with thanomin or Mercaptamine, the mol ratio of R-CN and thanomin or Mercaptamine is 1:2 ~ 1:6; The consumption of catalyst acetic acid copper is 1.5 ~ 2.5 times of molar weights of R-CN;
(2) after reaction finishes, gained mixture is cooled to room temperature, adds wherein methylene dichloride, then add 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, under room temperature, continue reaction;
(3) after reaction finishes, reaction solution is poured in 5～20% aqueous sodium hydroxide solution, with dichloromethane extraction, separated.
In above-mentioned steps (1), at 80-100
oClower reaction 5 ~ 10 hours.
In above-mentioned steps (2), 1 ~ 3 times of molar weight that the consumption of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is R-CN, at room temperature reacts 10 ~ 15 hours.
The first step reaction used catalyst of the present invention is cheap and easy to get, without preparation separately, and can react under condition of no solvent, has avoided the impact of using solvent to cause environment because of a large amount of.Second step reaction conditions of the present invention is gentle, at room temperature can react, and suitable substrates scope is wide, for the 2-oxazole of C-4, C-5 position unsubstituted and 2-thiazole synthetic provides a kind of practicable method.The present invention adopts one kettle way simple to operate, has saved unnecessary aftertreatment and separating-purifying step, has obtained higher productive rate, has broad application prospects.
Embodiment
In order more clearly to understand the present invention, below by specific embodiment, the present invention is described in further detail.
Specifically, the present invention, under condition of no solvent, mixes with thanomin or Mercaptamine aromatic nitriles, and adds wherein the neutralized verdigris of 1.5 ~ 2.5 times of amounts of aromatic nitriles, in 80-100 in the ratio of 1:2 ~ 1:6
oClower reaction 5 ~ 10 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein methylene dichloride, then add in batches wherein the DDQ(2 of 1 ~ 3 times of amount of aromatic nitriles, 3-bis-is chloro-5,6-dicyano-Isosorbide-5-Nitrae-benzoquinones), under room temperature, react 10 ~ 15 hours.After question response finishes, reaction solution is poured in 10% sodium hydroxide solution, with dichloromethane extraction, separated organic phase, with anhydrous sodium sulfate drying, steam except methylene dichloride, with column chromatography separation, obtain target product.
Synthesizing of embodiment 1:2-Ben Ji oxazole
Under condition of no solvent, 52 mg (0.5 mmol) cyanobenzene is mixed with 92 mg (1.5 mmol) thanomin, and add wherein 150 mg (0.75 mmol) neutralized verdigris, in 100
oClower reaction 10 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 15 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 64 mg, productive rate is 88%.
Data: MS (EI): m/z=145 [M]
+; IR (KBr): ν=3128,1587,1483,920,712 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 8.08 – 8.05 (m, 2H), 7.72 (s, 1H), 7.47 (dd,
j=5.1,2.0 Hz, 3H), 7.25 (s, 1H);
13c NMR (101 MHz, CDCl
3) δ 162.0,138.6,130.4,128.8,128.4,127.4,126.4.
Embodiment 2:2-(synthesizing of 4-aminomethyl phenyl) oxazole
Under condition of no solvent, 59 mg (0.5 mmol) 4-methyl benzonitrile is mixed with 92 mg (1.5 mmol) thanomin, and add wherein 150 mg (0.75 mmol) neutralized verdigris, in 100
ounder C, react 10 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 15 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 75 mg, productive rate is 94%.
Data: MS (EI): m/z=159 [M]
+; IR (KBr): ν=3126,2921,1613,1495,919,825,731 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 7.93 (d,
j=8.2 Hz, 2H), 7.66 (s, 1H), 7.25 (d,
j=8.3 Hz, 2H), 7.20 (s, 1H), 2.38 (s, 3H);
13c NMR (101 MHz, CDCl
3) δ 162.3,140.7,138.4,129.6,128.4,126.4,124.9,21.6.
Embodiment 3:2-(synthesizing of 4-chloro-phenyl-) oxazole
Under condition of no solvent, 69 mg (0.5 mmol) 4-chlorobenzonitrile is mixed with 92 mg (1.5 mmol) thanomin, and add wherein 150 mg (0.75 mmol) neutralized verdigris, in 100
oClower reaction 10 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 15 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 70 mg, productive rate is 78 %.
Data: Mp:81-83
oC; MS (EI): m/z=179[M]
+; IR (KBr): ν=3129,2924,1606,1480,1090,835,732 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 7.99 (d,
j=8.5 Hz, 2H), 7.72 (s, 1H), 7.45 (d,
j=8.5 Hz, 2H), 7.25 (s, 1H);
13c NMR (101 MHz, CDCl
3) δ 160.4,138.9,136.5,129.1,128.6,127.6,126.0.
Embodiment 4:2-(synthesizing of 4-cyano-phenyl) oxazole
Under condition of no solvent, 64 mg (0.5 mmol) para-Phthalonitrile is mixed with 92 mg (1.5 mmol) thanomin, and add wherein 150 mg (0.75 mmol) neutralized verdigris, in 100
oClower reaction 10 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 15 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 75 mg, productive rate is 88%.
Data: Mp:99-101
oc; MS (EI): m/z=170 [M]
+; IR (KBr): ν=3124,2229,1579,1489,1101,846,741 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 8.19 – 8.16 (m, 2H), 7.81 (d,
j=0.6 Hz, 1H), 7.80 – 7.77 (m, 2H), 7.34 – 7.33 (m, 1H);
13c NMR (101 MHz, CDCl
3) δ 160.1,139.8,132.7,131.2,129.2,126.8,118.4,113.7.
Synthesizing of embodiment 5:2-(2-pyridyl) thiazole
Under condition of no solvent, 52 mg (0.5 mmol) 2-cyanopyridine is mixed with 114 mg (1 mmol) Mercaptamine, and add wherein 250 mg (1.25 mmol) neutralized verdigris, in 80
oClower reaction 8 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 10 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 77 mg, productive rate is 95%.
Data: Mp:44-45
oC; MS (EI): m/z=162 [M]
+; IR (KBr): ν=1582,1463,1058,997,794,728,635 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 8.65 (d,
j=4.3 Hz, 1H), 8.26 (d,
j=7.9 Hz, 1H), 7.96 (d,
j=3.2 Hz, 1H), 7.85 (td,
j=7.8,1.7 Hz, 1H), 7.48 (d,
j=3.2 Hz, 1H), 7.36 (ddd,
j=7.5,4.9,1.1 Hz, 1H);
13c NMR (101 MHz, CDCl
3) δ 169.3,151.4,149.5,144.0,137.1,124.5,121.4,119.6.
Synthesizing of embodiment 6:2-(2-pyrimidyl) thiazole
Under condition of no solvent, 53 mg (0.5 mmol) 2-cyanopyrimidine is mixed with 114 mg (1 mmol) Mercaptamine, and add wherein 250 mg (1.25 mmol) neutralized verdigris, in 80
oClower reaction 8 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 10 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 57 mg, productive rate is 69%.
Data: Mp:96-98
oC; MS (EI): m/z=163 [M]
+; IR (KBr): ν=1557,1426,1024,805,627 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 8.89 (d,
j=4.9 Hz, 2H), 8.09 (d,
j=3.1 Hz, 1H), 7.59 (d,
j=3.1 Hz, 1H), 7.35 (t,
j=4.9 Hz, 1H);
13c NMR (101 MHz, CDCl
3) δ 166.7,159.6,157.8,145.2,123.1,120.8.
Synthesizing of embodiment 7:2-(2-thienyl) thiazole
Under condition of no solvent, 55 mg (0.5 mmol) 2-cyano thiophene is mixed with 114 mg (1 mmol) Mercaptamine, and add wherein 250 mg (1.25 mmol) neutralized verdigris, in 80
oClower reaction 8 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 170 mg (0.75 mmol) DDQ, under room temperature, react 10 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 77 mg, productive rate is 92%.
Data: MS (EI): m/z=167 [M]
+; IR (KBr): ν=3109,3079,1479,1142,1052,701,630 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 7.76 (d,
j=2.1 Hz, 1H), 7.52 (dd,
j=2.4,1.2 Hz, 1H), 7.39 (d,
j=5.1 Hz, 1H), 7.27-7.24 (m, 1H), 7.10-7.06 (m, 1H);
13c NMR (101 MHz, CDCl
3) δ 162.0,143.3,137.3,127.9,127.7,126.6,118.2.
Embodiment 8:1,4-bis-(2-thiazolyl) benzene synthetic
Under condition of no solvent, 64 mg (0.5 mmol) para-Phthalonitrile is mixed with 227 mg (2 mmol) Mercaptamine, and add wherein 250 mg (1.25 mmol) neutralized verdigris, in 80
oClower reaction 8 hours.After reaction finishes, gained mixture is cooled to room temperature, adds wherein 3 mL methylene dichloride, then add in batches wherein 340 mg (1.5 mmol) DDQ, under room temperature, react 10 hours.After reaction finishes, reaction solution is poured in the sodium hydroxide solution of 15 mL 10%, with 3 mL dichloromethane extraction three times, merge organic phase, with after anhydrous sodium sulfate drying, steam except methylene dichloride, by column chromatography separated (petrol ether/ethyl acetate=10:1), obtain target product output 105 mg, productive rate is 86%.
Data: Mp:153-155
oC; MS (EI): m/z=244 [M]
+; IR (KBr): ν=3109,2922,1475,1110,972,870,633 cm
-1;
1h NMR (400 MHz, CDCl
3) δ 8.07 (d,
j=0.6 Hz, 4H), 7.92 (d,
j=3.2 Hz, 2H), 7.39 (d,
j=3.2 Hz, 2H);
13c NMR (101 MHz, CDCl
3) δ 167.5,143.9,134.8,127.1,119.4.
Claims (8)
1. a synthetic method for 2-oxazole or 2-thiazole, is characterized in that taking following synthetic route:
X is S or O, and R is aryl, substituted aryl or heterocyclic radical;
(1), under condition of no solvent, R-CN is reacted under catalyst acetic acid copper exists with thanomin or Mercaptamine;
(2) after reaction finishes, gained mixture is cooled to room temperature, adds wherein methylene dichloride, then add 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, under room temperature, continue reaction;
(3) after reaction finishes, reaction solution is poured in 5～20% aqueous sodium hydroxide solution, with dichloromethane extraction, separation, obtained 2-oxazole or 2-thiazole.
2. the synthetic method of 2-oxazole according to claim 1 or 2-thiazole, is characterized in that: described substituted aryl is C
1～C
5alkyl, halogen radical, amino, cyano group, nitro, the aryl that thiazolyl, oxazolyl replaces.
3. the synthetic method of 2-oxazole according to claim 1 or 2-thiazole, is characterized in that: described heterocyclic radical is pyridyl, thienyl, pyrimidyl or pyrazinyl.
4. according to one of any described 2-oxazole of claims 1 to 3 or the synthetic method of 2-thiazole, it is characterized in that: the mol ratio of raw material R-CN and thanomin or Mercaptamine is 1:2 ~ 1:6.
5. the synthetic method of 2-oxazole according to claim 4 or 2-thiazole, is characterized in that: 1.5 ~ 2.5 times of molar weights that the consumption of catalyst acetic acid copper is R-CN.
6. the synthetic method of 2-oxazole according to claim 5 or 2-thiazole, is characterized in that: in step (1), at 80-100
oClower reaction 5 ~ 10 hours.
7. the synthetic method of 2-oxazole according to claim 5 or 2-thiazole, is characterized in that: in step (2), and 1 ~ 3 times of molar weight that the consumption of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is R-CN.
8. the synthetic method of 2-oxazole according to claim 7 or 2-thiazole, is characterized in that: in step (2), at room temperature react 10 ~ 15 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104693026A (en) * | 2014-09-24 | 2015-06-10 | 长沙理工大学 | Synthetic method of 1, 2-diol dicarboxylic ester |
| CN109053618A (en) * | 2018-02-22 | 2018-12-21 | 青岛科技大学 | Preparation method of oxazole derivative |
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| JPH05140129A (en) * | 1991-11-15 | 1993-06-08 | Kao Corp | Production of cyclic iminoether |
| CN1854128A (en) * | 2001-04-24 | 2006-11-01 | 麻省理工学院 | Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds |
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2013
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05140129A (en) * | 1991-11-15 | 1993-06-08 | Kao Corp | Production of cyclic iminoether |
| CN1854128A (en) * | 2001-04-24 | 2006-11-01 | 麻省理工学院 | Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds |
Non-Patent Citations (3)
| Title |
|---|
| XIANGNAN LI ET AL: "DDQ-Induced Dehydrogenation of Heterocycles for C-C Double Bond Formation: Synthesis of 2-Thiazoles and 2-Oxazoles", 《CHEM ASIAN J》, vol. 8, no. 7, 26 April 2013 (2013-04-26), pages 1409 - 1410 * |
| XIANGNAN LI ET AL: "Solvent-Free Tandem Synthesis of 2-Thiazolines and 2-Oxazolines Catalyzed by a Copper Catalyst", 《EUR J ORG CHEM》, no. 8, 3 February 2012 (2012-02-03), pages 1627 - 1629 * |
| 章小波 等: "抗抑郁药奈法唑酮中间体 2 -苯氧乙胺的合成工艺改进", 《精细化工中间体》, vol. 33, no. 5, 30 December 2003 (2003-12-30), pages 28 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104693026A (en) * | 2014-09-24 | 2015-06-10 | 长沙理工大学 | Synthetic method of 1, 2-diol dicarboxylic ester |
| CN104693026B (en) * | 2014-09-24 | 2016-08-17 | 长沙理工大学 | A kind of synthetic method of 1,2-glycol diesters |
| CN109053618A (en) * | 2018-02-22 | 2018-12-21 | 青岛科技大学 | Preparation method of oxazole derivative |
| CN109053618B (en) * | 2018-02-22 | 2022-05-13 | 青岛科技大学 | Preparation method of oxazole derivative |
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