CN101367824B - Preparation method for compound containing 1,2,3,11b-tetrahydric-[1,2] azine-[3,2-a] isoquinoline framework - Google Patents
Preparation method for compound containing 1,2,3,11b-tetrahydric-[1,2] azine-[3,2-a] isoquinoline framework Download PDFInfo
- Publication number
- CN101367824B CN101367824B CN2008102011077A CN200810201107A CN101367824B CN 101367824 B CN101367824 B CN 101367824B CN 2008102011077 A CN2008102011077 A CN 2008102011077A CN 200810201107 A CN200810201107 A CN 200810201107A CN 101367824 B CN101367824 B CN 101367824B
- Authority
- CN
- China
- Prior art keywords
- isoquinoline
- compound
- piperazine
- preparation
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Belonging to the technical field of organic chemistry, the present invention relates to a method for preparing a compound containing a 1, 2, 3, 11b-tetrahydro-[1, 2]azino[3, 2-a]isoquinoline framework. The method has the following characteristics: in solvent, compound (I) is catalyzed by trifluoromethanesulfonic acid silver salt to have the nucleophilic addition reaction of the first step, and then is catalyzed by trifluoromethanesulfonic acid ytterbium salt to have the dipolar cycloaddition reaction of the second step with cyclopropane derivative in order to obtain the compound containing the 1, 2, 3, 11b-tetrahydro-[1, 2]azino[3, 2-a]isoquinoline framework (II); wherein, R<1> is -H, -F, -C1, 4, 5-OCH2O-, a methyl group or a methoxyl group; R<2> is a phenyl group, p-methoxyphenyl or p-fluorophenyl; and R<3> is -H, a vinyl group, a phenyl group, a styryl group, p-methylphenyl, p-nitrophenyl and p-methoxyphenyl. The method has the following advantages: the yield can reach 92 percent in the process of cascade reaction; the range of applicable materials for reaction is wide; reaction operation is simple and convenient; the yield of product is high; and the application prospect in theresearch and development of new medicines is good.
Description
Technical field
The invention belongs to technical field of organic chemistry, be specifically related to a kind ofly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also.
Background technology
Organic molecule such as some natural products, natural product homologue, the compound with natural product skeleton or some non-natural compounds have important effect to the macromole of forming organism.Form the non-Cheng Jianzuo of some reversible and be used for the activity of regulation protein as utilizing between organic molecule and the protein, thereby study function ((a) B.R.Stockwell of the gene relevant with protein, Nature, 2004,432,846. (b) D.P.Walsh, Y.-T.Chang, Chem.Rev.2006,106,2476).Synthesize at the methodology of organic synthesis that uses the diversity guiding based on these people and to do a lot of work aspect the organic micromolecule compound storehouse with a certain ad hoc structure target.Among the micromolecular strategy of employed structure, be subjected to paying close attention to widely by the method for using cascade reaction to design and synthesize the natural framework compound of class, and the development cascade reaction has become research focus ((a) S.E.Denmark in the Synthetic Organic Chemistry field, A.Thorarensen, Chem.Rev.1996,96,137. (b) J.A.Jr.Porco, S.L.Schreiber, J.Am.Chem.Soc.1990,112,7410. (c) G.A.Molander, C.R.Harris, J.Am.Chem.Soc.1996,118,4059. (d) F.Shi, X.Li, Y.Xia, L.Zhang, Z.-X.Yu, J.Am.Chem.Soc.2007,129,15503.).
1, the 2-dihydro-isoquinoline all exists in many natural products and medicine as the advantage skeleton unit, and shows tangible biological activity.Some typical examples comprise: Papaverine (papaverine) makes slowly-releasing medicine of flaccid muscles (T.Kaneda, S.Nakajyo, J.Pharmacol.Sci.2005,98,275.); Saframycin-B, a kind of anti-tumor agents (Y.Mikami, K.Nakagaki, T.Arai, J.Pharm.Dyn.1981,4,282.); Indenoisoquinoline (indenoisoquinoline), topo isomerase I inhibitor (topoisomerase I inhibitor) (C.Marchand, Y.Pommier, Mol.Cancer Ther.2006,5,287.); Narcisline (narciclasine) also is a kind of antineoplastic inhibitor (G.R.Pettit, Y.Sagawa, J.Nat.Prod.1986,49,995.).Because 1,2-dihydro-isoquinoline structural unit plays important effect in the product of a large amount of natural products or design, develop new method and make up this parent ring, cater to genomics and chemicobiological demand, become a current research tendency, group such as our group and Asao has been more work ((a) Q.Ding in this respect, J.Wu, Org.Lett.2007,9,4959. (b) K.Gao, J.Wu, J.Org.Chem.2007,72,8611. (c) Q.Ding, Y.Ye, R.Fan, J.Wu, J.Org.Chem.2007,72,5439. (d) W.Sun, Q.Ding, X.Sun, J.Wu, J.Comb.Chem.2007,9,690. (e) S.Obika, Y.Takemoto, J.Org.Chem.2007,72,4462. (f) N.Asao, Y.Yamamoto, Angew.Chem.Int.Ed.2005,44,5526. (g) R.Yanada, Y.Takemoto, Angew.Chem.Int.Ed.2006,45,3822. (h) Ding, Q.; Wu, J.Adv.Synth.Catal.2008,350,1850. (i) Huo, Z.; Tomeba, H.; Yamamoto, Y.Tetrahedron Lett.2008,49,5531. (j) Yeom, H.-S.; Kim, S.; Shin, S.Synlett2008,924.)
People such as Kerr find in nearest research, at Yb (OTf)
3As 1,3 dipole (nitrone) under the katalysis of Lewis acid and dipolarophile body (active cyclopropane) [3+3] cycloaddition reaction can take place, generate the compound ((a) Young, the I.S. that contain 1,2 piperazine structural unit; Kerr, M.A.Angew.Chem.Int.Ed.2003,42,3023. (b) Young, I.S.; Kerr, M.A.Org.Lett.2004,6,139. (c) Young, I.S.; Williams, J.L.; Kerr, M.A.Org.Lett.2005,7,953. (d) Sibi, M.P.; Ma, Z.; Jasperse, C.P.J.Am.Chem.Soc.2005,127,5764. (e) Kang, Y.-B.; Sun, X.-L.; Tang, Y.Angew.Chem.Int.Ed.2007,46,3918).Studies show that in addition 1,2 piperazine structural unit exists in a lot of natural products and medicine, and show tangible biological activity, in some medicines synthetic also usually as useful as intermediates ((a) Pulz, R.; Al-Harrasi, A.; Rei β g, H.-U.Org.Lett.2002,4,2353. (b) Tishkov, A.A.; Rei β g, H.-U.; Ioffe, S.L.Synlett2002,863. (c) Buchholz, M.; Rei β g, H.-U.Eur.J.Org.Chem.2003,3524. (d) Al-Harrasi, A.; Rei β g, H.-U.Angew.Chem.Int.Ed.2005,44,6227. (e) Carson, C.A.; Kerr, M.A.Angew.Chem.Int.Ed.2006,45,6560).
Summary of the invention
Technical problem to be solved by this invention is to provide the preparation of a kind of high-efficient simple ground to contain 1,2,3, and 11b-tetrahydrochysene-[1,2] piperazine is the method for [3,2-a] isoquinoline 99.9 framework compound also.
The present invention solves the problems of the technologies described above the technical scheme of being taked, a kind ofly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, in solvent, compound (I) carries out the first step nucleophilic addition under the catalysis of Lewis acid catalyst silver trifluoromethanesulfonate (AgOTf); Again at Ytterbiumtriflate (Yb (OTf)
3) catalysis under, in reaction system, add cyclopropane derivative (dipolarophile body) and carry out the second step Dipolar Cycloaddition, make and contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is [3,2-a] isoquinoline 99.9 framework compounds (II) also, reaction formula is:
Wherein, R
1Be various electron-donating groups, as :-H, 4,5-OCH
2O-(condensed ring group), methyl or methoxy etc., or various electron-withdrawing group-F ,-Cl etc.;
R
2For containing the aryl of various confession/electron-withdrawing groups, as: phenyl (Ph), p-methoxyphenyl (p-MeO-C
6H
4), to fluorophenyl (p-F-C
6H
4) etc.;
R
3Be-H, vinyl, phenyl, styryl, p-methylphenyl, p-nitrophenyl, p-methoxyphenyl etc.
After the reaction, adopt conventional steps to extract, be specially: the reaction solution decompression is spin-dried for, with washing reaction liquid such as the saturated common salt aqueous solution, with the DCM extraction, drying concentrates and column chromatography for separation is contained 1,2 accordingly, 3,11b-tetrahydrochysene-[1,2] piperazine is [3,2-a] iloquinoline derivative framework compound also.
The present invention uses AgOTf as the Lewis acid catalyst from oxime, and the various benzaldoximes of catalysis ortho position alkynyl substituted in solvent generate 1,3 dipole (nitrone) at intramolecularly nucleophilic addition(Adn) cyclization; On this basis, at Yb (OTf)
3Catalysis under nitrone and dipolarophile body (cyclopropane derivative) [3+3] dipole cycloaddition reaction takes place again, make up two rings by two step of " one kettle way " series connection cyclizations are efficient, make simple and effective and contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine [3,2-a] iloquinoline derivative framework compound storehouse also.
On the basis of such scheme, described solvent is a toluene, tetrahydrofuran (THF), acetonitrile (CN
3CN), dimethyl formamide (DMF), methylene dichloride (CH
2Cl
2) or ethylene dichloride ((CH
2Cl)
2).
On the basis of such scheme, in compound (I) preparation isoquinoline 99.9 framework compound (II) reaction, compound (I) is 2～1:1 with the mol ratio of cyclopropane derivative.
On the basis of such scheme, in the first step nucleophilic addition, compound (I) is 1:0.01～0.05 with the mol ratio of silver trifluoromethanesulfonate.
Concrete compound (I) can be 1:0.01,0.015,0.02,0.025,0.03,0.035,0.04,0.045 or 0.05 with the mol ratio of silver trifluoromethanesulfonate.
On the basis of such scheme, the condition of nucleophilic addition is 70～90 ℃, and 1～10 minute reaction times is to TLC detection complete reaction.
Concrete, temperature of reaction can be 70,75,80,85 or 90 ℃;
Reaction times can be 1,2,3,5,6,8 or 10 minutes.
On the basis of such scheme, in the second step Dipolar Cycloaddition, the mol ratio of compound (I) and cyclopropane derivative can be 2,1.9,1.8,1.7,1.6,1.5,1.4,1.3,1.2,1.1 or 1:1.
The mol ratio of cyclopropane derivative and Ytterbiumtriflate is 1:0.05～0.15.
Concrete, the mol ratio of cyclopropane derivative and Ytterbiumtriflate can be 1:0.05,0.06,0.08,0.10,0.12,0.13 or 0.15.
The condition of Dipolar Cycloaddition is 100～120 ℃, continues reaction, 6～12 hours reaction times down in reflux state.
Concrete, temperature of reaction can be 100,105,110,115 or 120 ℃;
Reaction times can be 6,7,8,9,10,11 or 12 hours.
The invention has the beneficial effects as follows:
Yield in the tandem reactor process of the present invention reaches 92%, and reaction raw materials is applied widely, and operation of the present invention is easy, and the product yield height has extraordinary application prospect in new drug development.
Embodiment
Embodiment 1
1,1 (11bH)-dioctyl phthalate methoxycarbonyl-6-phenyl-2,3-dihydro-[1,2] piperazine is the preparation of [3,2, a] isoquinoline 99.9 also:
With 2-(2-phenylacetylene base) benzaldoxime (0.6mmol), 5mol%AgOTf (being 2-(2-phenylacetylene base) benzaldoxime and AgOTf mol ratio 1:0.05) is dissolved in the 6ml organic solvent toluene, stirs 5 minutes down in 80 ℃, and TLC follows the tracks of and detects complete reaction; In reaction system, add dipolarophile body 1 then, and 1-dioctyl phthalate methoxycarbonyl cyclopropane (0.4mmol) and 10mol% (promptly 1,1-dioctyl phthalate methoxycarbonyl cyclopropane and Yb (OTf)
3Mol ratio 1:0.1), continue under the reflux state and reacted 12 hours, TLC follows the tracks of and detects complete reaction.Decompression is spin-dried for solvent down, and DCM extracts (10mL * 2), anhydrous Na
2SO
4Drying, concentrating also, column chromatography for separation gets light yellow thick liquid: 1,1 (11bH)-dioctyl phthalate methoxycarbonyl-6-phenyl-2,3-dihydro-[1,2] piperazine is [3,2, a] isoquinoline 99.9 also, and it is 77% that yield reaches;
1H NMR (400MHz, CDCl
3) δ 1.87 (dd, J=8.3,8.3Hz, 1H), 2.15 (dd, J=7.8,7.8Hz, 1H), 3.65-3.75 (m, 4H), 3.78-3.86 (m, 4H), 5.69 (s, 1H), 6.40 (s, 1H), 7.31-7.48 (m, 6H), 7.54 (d, J=6.8Hz, 1H), 7.98 (d, J=7.8Hz, 2H);
13C NMR (100MHz, CDCl
3) δ 32.2,52.8,53.1,62.5,64.7,67.5,127.0,127.5,128.2,128.4,128.5,129.3,130.6,133.9,137.5,137.8,169.4,169.5,169.9.
Embodiment 2
1,1 (11bH)-dioctyl phthalate methoxycarbonyl-6-(4-p-methoxy-phenyl)-2,3-dihydro-[1,2] piperazine is the preparation of [3,2, a] isoquinoline 99.9 also:
With 2-(2-(4-p-methoxy-phenyl) ethynyl) benzaldoxime (0.6mmol), 5mol%AgOTf is dissolved in the 6ml organic solvent toluene, stirred 5 minutes down in 80 ℃, TLC follows the tracks of and detects complete reaction, in reaction system, add dipolarophile body 1,1-dioctyl phthalate methoxycarbonyl cyclopropane (0.4mmol) and 10mol%Yb (OTf) then
3, continuing under the reflux state and reacted 12 hours, TLC follows the tracks of and detects complete reaction.
Decompression is spin-dried for solvent down, and DCM extracts (10mL * 2), anhydrous Na
2SO
4Drying, concentrating also, column chromatography for separation gets light yellow thick liquid: 1,1 (11bH)-dioctyl phthalate methoxycarbonyl-6-(4-p-methoxy-phenyl)-2,3-dihydro-[1,2] piperazine is [3,2, a] isoquinoline 99.9 also, and yield is 74%;
1H NMR (400MHz, CDCl
3) δ 1.84 (dd, J=8.3,8.3Hz, 1H), 2.15 (dd, J=7.8,7.8Hz, 1H), 3.65-3.80 (m, 4H), 3.82-3.95 (m, 7H), 5.69 (s, 1H), 6.36 (s, 1H), 6.94 (d, J=8.8Hz, 2H), 7.34-7.43 (m, 3H), 7.54 (d, J=6.8Hz, 1H), 7.95 (d, J=8.8Hz, 2H);
13C NMR (100MHz, CDCl
3) δ 32.2,52.7,53.0,62.5,64.5,64.7,67.3,113.8,127.5,128.2,128.3,128.7,129.3,130.1,134.1,137.8,161.7,168.8,169.5,169.6.
Embodiment 3
1,1 (11bH)-dioctyl phthalate methoxycarbonyl-10-fluoro-6-phenyl-2,3-dihydro-[1,2] piperazine is the preparation of [3,2, a] isoquinoline 99.9 also:
With 5-fluoro-2-(2-phenylacetylene base) benzaldoxime (0.6mmol), 5mol%AgOTf is dissolved in the 6ml toluene, stirred 5 minutes down in 80 ℃, TLC follows the tracks of and detects complete reaction, in reaction system, add dipolarophile body 1,1-dioctyl phthalate methoxycarbonyl cyclopropane (0.4mmol) and 10mol%Yb (OTf) then
3, continuing under the reflux state and reacted 12 hours, TLC follows the tracks of and detects complete reaction.
Decompression is spin-dried for solvent down, and DCM extracts (10mL * 2), anhydrous Na
2SO
4Drying, concentrating also, column chromatography for separation gets light yellow thick liquid: 1,1 (11bH)-dioctyl phthalate methoxycarbonyl-10-fluoro-6-phenyl-2,3-dihydro-[1,2] piperazine is [3,2, a] isoquinoline 99.9 also, and yield is 92%;
1HNMR (400MHz, CDCl
3) δ 1.81 (dd, J=8.3,8.3Hz, 1H), 2.21 (dd, J=7.8,7.8Hz, 1H), 3.65-3.78 (m, 4H), 3.81-3.90 (m, 4H), 5.69 (s, 1H), 6.37 (s, 1H), 7.08 (dt, J=2.4,8.0Hz, 1H), 7.32 (dd, J=2.4,9.2Hz, 1H), 7.37-7.46 (m, 4H), 7.97 (dd, J=1.5,7.8Hz, 2H);
13C NMR (100MHz, CDCl
3) δ 32.1,52.9,53.1,62.5,64.5,64.6,66.8,114.7 (
2J
CF=22.0Hz), 115.5 (
2J
CF=21.0Hz), 127.0,128.5,130.1,130.7,131.0 (
3J
CF=7.6Hz), 137.2,140.0 (
3J
CF=7.6Hz), 162.2 (
1J
CF=246.7Hz), 169.2,169.3,169.6.
Embodiment 4
1,1 (11bH)-dioctyl phthalate methoxycarbonyl-10-fluoro-6-(4-p-methoxy-phenyl)-2,3-dihydro-[1,2] piperazine is the preparation of [3,2, a] isoquinoline 99.9 also:
With 5-fluoro-2-(2-(4-p-methoxy-phenyl) ethynyl) benzaldoxime (0.6mmol), 5mol%AgOTf is dissolved in the 6ml organic solvent toluene, stirred 5 minutes down in 80 ℃, TLC follows the tracks of and detects complete reaction, in reaction system, add dipolarophile body 1,1-dioctyl phthalate methoxycarbonyl cyclopropane (0.4mmol) and 10mol%Yb (OTf) then
3, continuing under the reflux state and reacted 12 hours, TLC follows the tracks of and detects complete reaction.
Decompression is spin-dried for solvent down, and DCM extracts (10mL * 2), anhydrous Na
2SO
4Drying, concentrating also, column chromatography for separation gets light yellow thick liquid: 1,1 (11bH)-dioctyl phthalate methoxycarbonyl-10-fluoro-6-(4-p-methoxy-phenyl)-2,3-dihydro-[1,2] piperazine is [3,2, a] isoquinoline 99.9 also, and yield is 78%;
1H NMR (400MHz, CDCl
3) δ 1.77 (dd, J=8.8,8.8Hz, 1H), 2.19 (dd, J=7.8,7.8Hz, 1H), 3.66-3.72 (m, 1H), 3.75 (s, 1H), 3.82-3.89 (m, 7H), 5.68 (s, 1H), 6.33 (s, 1H), 6.94 (d, J=8.8Hz, 2H), 7.07 (dt, J=2.4,8.3Hz, 1H), 7.32 (dd, J=2.4,9.2Hz, 1H), 7.39 (dd, J=8.3,8.3Hz, 1H), 7.94 (d, J=8.8Hz, 2H);
13C NMR (100MHz, CDCl
3) δ 32.1,52.9,53.1,62.5,64.4,64.5,66.6,113.9,114.8 (d,
2J
CF=21.9Hz), 115.5 (d,
2J
CF=21.9Hz), 128.7,129.8,130.4,130.9 (d,
3J
CF=8.6Hz), 140.1 (d,
3J
CF=7.6Hz), 161.8,162.2 (
1J
CF=246.9Hz), 168.5,169.4.
Claims (7)
1. one kind contains 2,3, and 11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, and compound (I) carries out the first step nucleophilic addition under the catalysis of silver trifluoromethanesulfonate in solvent, forms reaction system; The adding cyclopropane derivative carries out the second step Dipolar Cycloaddition in the catalysis downhill reaction system of Ytterbiumtriflate again, makes to contain 1,2,3, and 11b-tetrahydrochysene-[1,2] piperazine is [3,2-a] isoquinoline 99.9 framework compounds (II) also, and reaction formula is:
Wherein, R
1For-H ,-F ,-Cl, methyl or methoxy;
R
2For phenyl, p-methoxyphenyl or to fluorophenyl;
R
3Be-H, vinyl, phenyl, styryl, p-methylphenyl, p-nitrophenyl, p-methoxyphenyl.
2. according to claim 1ly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, it is characterized in that: described solvent is toluene, tetrahydrofuran (THF), acetonitrile, dimethyl formamide, methylene dichloride or ethylene dichloride.
3. according to claim 1 and 2ly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, it is characterized in that: in the first step nucleophilic addition, compound (I) is 1: 0.01～0.05 with the mol ratio of silver trifluoromethanesulfonate.
4. according to claim 3ly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, it is characterized in that: the condition of nucleophilic addition is 70～90 ℃, 1～10 minute reaction times.
5. according to claim 1 and 2ly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine also [3,2-a] preparation method of isoquinoline 99.9 framework compound, it is characterized in that: in compound (I) preparation isoquinoline 99.9 framework compound (II) reaction, compound (I) is 2～1: 1 with the mol ratio of cyclopropane derivative.
6. according to claim 5ly contain 1,2,3,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, it is characterized in that: in the second step Dipolar Cycloaddition, the mol ratio of cyclopropane derivative and Ytterbiumtriflate is 1: 0.05～0.15.
7. describedly contain 1,2,3 according to claim 1 or 6,11b-tetrahydrochysene-[1,2] piperazine is the preparation method of [3,2-a] isoquinoline 99.9 framework compound also, it is characterized in that: the condition of Dipolar Cycloaddition is 100～120 ℃, 6～12 hours reaction times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008102011077A CN101367824B (en) | 2008-10-13 | 2008-10-13 | Preparation method for compound containing 1,2,3,11b-tetrahydric-[1,2] azine-[3,2-a] isoquinoline framework |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008102011077A CN101367824B (en) | 2008-10-13 | 2008-10-13 | Preparation method for compound containing 1,2,3,11b-tetrahydric-[1,2] azine-[3,2-a] isoquinoline framework |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101367824A CN101367824A (en) | 2009-02-18 |
| CN101367824B true CN101367824B (en) | 2011-11-16 |
Family
ID=40411849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008102011077A Expired - Fee Related CN101367824B (en) | 2008-10-13 | 2008-10-13 | Preparation method for compound containing 1,2,3,11b-tetrahydric-[1,2] azine-[3,2-a] isoquinoline framework |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101367824B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101265231A (en) * | 2008-05-08 | 2008-09-17 | 复旦大学 | Method for preparing isoquinoline-N-oxide |
-
2008
- 2008-10-13 CN CN2008102011077A patent/CN101367824B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101265231A (en) * | 2008-05-08 | 2008-09-17 | 复旦大学 | Method for preparing isoquinoline-N-oxide |
Non-Patent Citations (5)
| Title |
|---|
| Hyun-suk yeom.et al..Silver(I)-Catalyzed Direct Route to Isoquinoline-N-Oxides.《SYNLETT》.2008,(第6期),第924-928页. * |
| Ian S. Young. et al..A Homo [3+2] Dipolar Cycloaddition: The Reaction of Nitrones with Cyclopropanes.《Angewandte Chemie International Edition》.2003,第42卷第3023-3026页. * |
| Ian S.Young.et al..Three-Component Homo 3 + 2 Dipolar Cycloaddition. A Diversity-Oriented Synthesis of Tetrahydro-1,2-oxazines and FR900482 Skeletal Congeners.《Orgnic letters》.2003,第6卷(第1期),第139-141页. * |
| IanS.Young.etal..Three-ComponentHomo3+2DipolarCycloaddition.ADiversity-OrientedSynthesisofTetrahydro-1 2-oxazines and FR900482 Skeletal Congeners.《Orgnic letters》.2003 |
| Zhibao Huo.et al..Iodine-mediated electrophilic cyclization of 2-alkynylbenzaldoximes leading to the formation of iodoisoquinoline N-oxides.《Tetrahedron Letters》.2008,第49卷第5531-5533页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101367824A (en) | 2009-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yeung et al. | Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate | |
| Chari et al. | Nanoporous aluminosilicate catalyst with 3D cage-type porous structure as an efficient catalyst for the synthesis of benzimidazole derivatives | |
| Jiang et al. | A new rapid multicomponent domino reaction for the formation of functionalized benzo [h] pyrazolo [3, 4-b] quinolines | |
| Xiong et al. | Synthesis of the 6, 6, 5, 7-tetracyclic core of daphnilongeranin B | |
| Rao et al. | Catalyst-free one-pot domino reactions for selective synthesis of functionalized 2, 8-oxazabicyclo [3.3. 1]-nonanes and 5 H-indeno [1, 2-b] pyridin-5-ones | |
| Sun et al. | An organocatalytic hydroalkoxylation/Claisen rearrangement/Michael addition tandem sequence: Divergent synthesis of multi-substituted 2, 3-dihydrofurans and 2, 3-dihydropyrroles from cyanohydrins | |
| Xiao et al. | Amide-assisted intramolecular [3+ 2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine | |
| Qing et al. | One-pot synthesis of 2, 4, 6-triarylpyridines from β-nitrostyrenes, substituted salicylic aldehydes and ammonium acetate | |
| CN110551070A (en) | Synthesis of camphoryl pyrimidine compounds and antitumor activity thereof | |
| CN102977097B (en) | A kind of sweet-smelling alkynyl substituted indole oxazine derivative and its production and use | |
| Wang et al. | Asymmetric total synthesis of (−)-δ-lycorane | |
| Zhang et al. | A biomass-involved strategy for the synthesis of N-arylated dibenzo [b, e][1, 4] oxazepin-11 (5 H)-ones, acridones, 7, 12-dihydrodibenzo [b, e][1, 4] oxazocin-6 H-ones and dibenzo [b, f] azepin-10 (11 H)-ones | |
| CN101367824B (en) | Preparation method for compound containing 1,2,3,11b-tetrahydric-[1,2] azine-[3,2-a] isoquinoline framework | |
| CN104610267B (en) | Method for efficiently synthesizing 6-alkyl pyrazolo [1,5-c ] quinazoline framework compound under non-catalytic condition | |
| CN112707795A (en) | Preparation method of Icetexane type abietane diterpene | |
| CN115093372B (en) | Synthesis method of imidazole derivative | |
| CN104045643B (en) | A kind of method that copper catalysis water phase prepares pyrazolo [1,5-c] quinazoline framework compound | |
| SAKAMOTO et al. | Condensed Heteroaromatic Ring Systems. VI.: Synthesis of Indoles and Pyroolopyridines from o-Nitroarylacetylenes | |
| CN101786983A (en) | Method for preparing 2-amino-1,2-dihydro-isoquinoline compound | |
| CN102329281B (en) | C-acyl-dihydro sulfinpyrazone based on catalysis of chiral bicyclic imidazole nucleophilic catalyst and preparation method thereof | |
| CN109320488B (en) | Water phase one-pot synthesis method of 3-hydroxyflavone and derivatives thereof | |
| CN107474059A (en) | Dodecyloxy phenyl porphyrin benzamide hexyl imidodicarbonic diamide decyloxy hexyloxy benzophenanthrene ternary compound | |
| CN109369772B (en) | Synthetic method and anti-tumor application of phenanthridine nitidine derivatives | |
| CN102659512B (en) | Preparation method of halogenated benzo [ a ] fluorenol | |
| Witulski et al. | Application to the synthesis of natural products |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20111116 Termination date: 20141013 |
|
| EXPY | Termination of patent right or utility model |