CN113429450A - Diterpenoid anti-inflammatory compound containing indole skeleton and preparation method thereof - Google Patents
Diterpenoid anti-inflammatory compound containing indole skeleton and preparation method thereof Download PDFInfo
- Publication number
- CN113429450A CN113429450A CN202010208332.4A CN202010208332A CN113429450A CN 113429450 A CN113429450 A CN 113429450A CN 202010208332 A CN202010208332 A CN 202010208332A CN 113429450 A CN113429450 A CN 113429450A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- reaction
- diterpenoid
- indole skeleton
- 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.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Abstract
The invention provides a diterpenoid anti-inflammatory compound containing an indole skeleton and a preparation method thereof, wherein the compound has a structure shown in a formula I:
R1selected from hydrogen, halogen or methoxy, wherein R1The positions and the number of the (C) can be unfixed. The preparation method provided by the invention can efficiently and quickly synthesize the diterpene compound containing the indole skeleton with the anti-inflammatory effect. The preparation method comprises the steps of adding the compound shown as the formula A, a solvent, oxalyl chloride and dimethylformamide into a reaction bottle at normal temperature, uniformly stirring at room temperature for reaction, and detecting the reaction end point by TLC; carrying out decompression spin-drying on the reaction product; adding a compound shown in the formula B, a solvent, triphenylphosphine and alkali into the obtained product, then placing the reaction system at room temperature for uniform stirring reaction, and detecting the reaction end point by TLC; and separating and purifying the reaction system to obtain the target compound shown in the formula I. The compound is two kindsThe plant pathogenic fungi Fusarium oxysporum and Verticillium have high and continuous antibacterial activity.
Description
Technical Field
The invention relates to the field of organic chemical synthesis, in particular to diterpene anti-inflammatory compounds containing indole frameworks and a preparation method thereof, and more particularly relates to a preparation method of compounds shown in a formula I.
Background
Terpenoids are the most structurally diverse compounds in the natural product family and are present in most organisms, playing an important role in the operation of the mechanisms of the organisms. The terpenoid is formed by connecting isoprene units or isopentane units in various ways, and has a general formula (C)5H8)nIn particular, diterpenoids are a population of compounds consisting of 4 isoprene units and containing 20 carbon atoms. Diterpenoid compounds have wide physiological activities and important practical and economic values in the aspects of production such as medicine, industry, agriculture and the like, for example: in the pharmaceutical industry, diterpenoids have antitumor activity, analgesic activity, antifungal and anti-inflammatory effects, and insect antifeedant effect. On the other hand, indole ring system compounds are also frequently used as intermediates for pharmaceuticals, agrochemicals and numerous fine chemicals. Particularly in the aspect of medicine, the indole derivative has the functions of diminishing inflammation, easing pain, reducing blood pressure, resisting tumors and the like. Therefore, the patent provides a quick and efficient method for synthesizing diterpenoid anti-inflammatory compounds containing indole skeletons. Through the combination of the two dominant skeletons, the compound shows excellent activity in the aspects of anti-tumor and anti-inflammation.
Disclosure of Invention
In view of the above technical problems, a first aspect of the present invention: a diterpenoid anti-inflammatory compound containing an indole skeleton is provided, and the compound is a compound shown as a formula I or a pharmaceutically acceptable salt, a crystalline hydrate or a solvate of the compound shown as the formula I:
wherein R is1Selected from hydrogen, halogen (said halogen includes chlorine or bromine) or methoxy, wherein R1The positions and the number of the (C) can be unfixed.
The diterpenoid anti-inflammatory compound containing the indole skeleton is characterized by being a compound shown as a formula I, and having a structure shown as follows:
wherein R is1Selected from hydrogen, halogen or methoxy, wherein R1The positions and the number of the (C) can be unfixed.
The compounds also include pharmaceutically acceptable salts, crystalline hydrates or solvates.
The halogen includes chlorine or bromine.
The compound shown in the formula I as a preferred scheme comprises any one of the following compounds:
in a second aspect of the invention: there is provided a process for preparing a compound as hereinbefore described, which process, according to an embodiment of the invention, comprises:
combining a compound of formula a with a compound of formula B to synthesize a compound of formula I:
wherein R is1As previously described.
According to the embodiment of the invention, the compound shown as the formula A is firstly reacted with oxalyl chloride to generate acyl chloride of the compound shown as the formula A, then the acyl chloride of the compound shown as the formula A is contacted with the compound shown as the formula B, triphenylphosphine and alkali in an organic solvent, and the reaction is carried out under the condition of room temperature and stirring.
According to the embodiment of the invention, the molar charge ratio of the compound shown as the formula A, the oxalyl chloride, the N, N-dimethylformamide, the compound shown as the formula B and the triphenylphosphine is 1.1-1.3:3-4:0.05-0.15:1: 1.1-1.2.
According to the embodiment of the invention, the feeding sequence of the first step of the method is the compound shown as A, dichloromethane, oxalyl chloride and N, N-dimethylformamide; the second step is to feed the compound shown as the formula B, dichloromethane, triphenylphosphine, cesium hydroxide monohydrate and acyl chloride of the compound shown as the formula A.
Optionally, the organic solvent used in the present invention is dichloromethane, or tetrahydrofuran, or diethyl ether.
According to an embodiment of the invention, the base used in the invention is cesium hydroxide monohydrate, or cesium carbonate or triethylamine.
According to some embodiments of the invention, further comprising: and (2) separating and purifying the compound shown in the formula I by silica gel column chromatography, wherein a mixture of petroleum ether and ethyl acetate is used as a separation phase, and the volume ratio of the petroleum ether to the ethyl acetate is 40: 1-10: 1.
Thus, in accordance with an embodiment of the present invention, the present invention provides a synthetic route that can be used to prepare compounds of formula I:
in the reaction, sequentially adding the compound shown in the formula A, oxalyl chloride, dichloromethane and N, N-dimethylformamide into a reaction bottle at room temperature, then, uniformly stirring the reaction system at room temperature for reaction for 1-2 hours, and then, carrying out reduced pressure desolventization at low temperature to obtain the acyl chloride of the compound shown in the formula A; and then adding the compound shown in the formula B, dichloromethane, triphenylphosphine, cesium hydroxide monohydrate and acyl chloride of the compound shown in the formula A into a reaction bottle. Then, the reaction system is placed in room temperature to be evenly stirred for reaction, the TLC detects the end point of the reaction, and V is usedPetroleum ether：VEthyl acetateThe target compound shown in the formula I is directly obtained by chromatography with 40: 1-10: 1 column, the melting point of the target compound is tested by using a melting point instrument, an NMR spectrum is tested by using a 400-meganuclear magnetic resonance spectrometer, deuterated chloroform is used as a solvent in the test, high resolution is tested and analyzed on a mass spectrometer, and infrared is tested on an IR spectrometer.
Description of the reaction procedure
The compound of the formula A reacts with oxalyl chloride to form corresponding acyl chloride under the condition of catalytic amount of N, N-dimethylformamide, and simultaneously the compound of the formula B reacts with triphenylphosphine under alkaline condition to form quaternary phosphonium salt, the NHTs segment of the quaternary phosphonium salt reacts with the acyl chloride to form novel tosyl protected amide, and the amide segment can react with intramolecular quaternary phosphonium salt under alkaline condition to form terpenoid compound containing indole skeleton.
Drawings
The invention will be further explained with reference to the drawings.
FIG. 1 is a 1H NMR chart of Compound I-1 in deuterated chloroform.
FIG. 2 is a 13C NMR chart of Compound I-1 in deuterated chloroform.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the scope of the examples.
Example 1
A method for the synthesis of (8R, 9S, 10S, 13R, 14S, 17R) -10, 13-dimethyl-17- ((R) -4- (1-tosyl-1H-indol-2-yl) butandin-2-yl) dodecyl-3H-cyclopenta [ a ] phenanthrene-3, 7,12(2H, 4H) -trione comprising the following experimental steps:
dehydrocholic acid A-1(1.2mmol,483.1mg), dichloromethane (3mL), oxalyl chloride (3.6mmol,453.3mg), N, N-dimethylformamide (0.06mmol,4.3mg) were added to 10mL Schlenk flash at room temperature, the system was left to react at room temperature for 1 hour, the end of the reaction was checked by TLC point plate, and then the solvent and excess oxalyl chloride were removed at low temperature under reduced pressure on a rotary evaporator to give dehydrocholic acid A-1 derived acid chloride. Then N- (2- (chloromethyl) phenyl) -4-methylbenzenesulfonamide B-1(295.6mg, 1.0mmol), dichloromethane (5mL), triphenylphosphine (288.6mg, 1.1mmol) and cesium hydroxide monohydrate (419.6mg, 2.5 mmol) are added into the obtained acyl chloride, and the mixture is placed in a room temperature for reaction for 72 hours, detected by a TLC point plate, and separated and purified by column chromatography to obtain a target compound I-1 which is a white solid with the yield of 50%.
Melting point: 159 ℃ and 160 ℃.
1H NMR(400MHz,CDCl3):δ8.16(d,J＝8.3Hz,1H),7.61(d,J＝8.4Hz,2H),7.41(d,J＝7.2Hz,1H),7.27-7.16(m,4H),6.37(s,1H),3.05(ddd,J＝15.9,11.2,4.6Hz,1H),2.96-2.84(m,4H),2.37(dd,J＝12.6,5.1Hz,1H),2.33(s,3H),2.30-2.24(m,2H),2.23-1.94(m,8H),1.87(td,J＝11.3,7.1Hz,1H),1.71-1.53(m,2H),1.49(ddd,J＝12.8,10.6,4.7Hz,1H),1.41(s,3H),1.37-1.23(m,3H),1.09(s,3H),0.95(d,J＝6.5Hz,3H),0.90-0.82(m,2H):δ212.05,209.11,208.79,144.59,142.68,137.14,136.09,129.76,129.73(2C),126.18(2C),123.73,123.41,120.00,114.76,108.57,56.90,51.71,48.95,46.80,45.78,45.51,44.95,42.75,38.62,36.46,36.00,35.97,35.21,34.91,27.64,26.38,25.13,21.87,21.52,18.96,11.87。
High resolution: c38H45NO5S[M+Na+](ii) a Theoretical value: 650.2911, actual test value: 650.2912.
infrared test values: 2971,1709,1449,1377,1175,1092,814,748,588,540cm-1。
Example 2
A method for the synthesis of (8R, 9S, 10S, 13R, 14S, 17R) -10, 13-dimethyl-17- ((R) -4- (5-methoxy-1-tosyl-1H-indol-2-yl) butandin-2-yl) dodecyl-3H-cyclopenta [ a ] phenanthrene-3, 7,12(2H, 4H) -trione comprising the following experimental steps:
dehydrocholic acid A-1(1.2mmol,483.1mg), dichloromethane (3mL), oxalyl chloride (3.6mmol,453.3mg), N, N-dimethylformamide (0.06mmol,4.3mg) were added to 10mL Schlenk flash at room temperature, the system was left to react at room temperature for 1 hour, the end of the reaction was checked by TLC point plate, and then the solvent and excess oxalyl chloride were removed at low temperature under reduced pressure on a rotary evaporator to give dehydrocholic acid A-1 derived acid chloride. Then N- (2- (chloromethyl) -4-methoxyphenyl) -4-methylbenzenesulfonamide B-2(325.7mg,1.0mmol), dichloromethane (5mL), triphenylphosphine (288.6mg, 1.1mmol) and cesium hydroxide monohydrate (419.6mg, 2.5 mmol) were added to the above obtained acid chloride, and the mixture was left to react at room temperature for 72 hours, detected by TLC dot plate, and the reaction system was separated and purified by column chromatography to obtain the objective compound I-2 as a white solid with a yield of 52%.
Example 3
A method for the synthesis of (8R, 9S, 10S, 13R, 14S, 17R) -10, 13-dimethyl-17- ((R) -4- (5-bromo-1-tosyl-1H-indol-2-yl) butadan-2-yl) dodecyl-3H-cyclopenta [ a ] phenanthrene-3, 7,12(2H, 4H) -trione comprising the following experimental steps:
dehydrocholic acid A-1(1.2mmol,483.1mg), dichloromethane (3mL), oxalyl chloride (3.6mmol,453.3mg), N, N-dimethylformamide (0.06mmol,4.3mg) were added to 10mL Schlenk flash at room temperature, the system was left to react at room temperature for 1 hour, the end of the reaction was checked by TLC point plate, and then the solvent and excess oxalyl chloride were removed at low temperature under reduced pressure on a rotary evaporator to give dehydrocholic acid A-1 derived acid chloride. Then N- (2- (chloromethyl) -4-bromophenyl) -4-methylbenzenesulfonamide B-3(374.7mg, 1.0mmol), dichloromethane (5mL), triphenylphosphine (288.6mg, 1.1mmol) and cesium hydroxide monohydrate (419.6mg, 2.5 mmol) are added to the obtained acyl chloride, and the mixture is placed at room temperature for reaction for 72 hours, detected by a TLC point plate, and separated and purified by column chromatography to obtain the target compound I-3 in white solid with the yield of 56%.
Example 4
A method for the synthesis of (8R, 9S, 10S, 13R, 14S, 17R) -10, 13-dimethyl-17- ((R) -4- (5-chloro-1-tosyl-1H-indol-2-yl) butandin-2-yl) dodecyl-3H-cyclopenta [ a ] phenanthrene-3, 7,12(2H, 4H) -trione comprising the following experimental steps:
dehydrocholic acid A-1(1.2mmol,483.1mg), dichloromethane (3mL), oxalyl chloride (3.6mmol,453.3mg), N, N-dimethylformamide (0.06mmol,4.3mg) were added to 10mL Schlenk flash at room temperature, the system was left to react at room temperature for 1 hour, the end of the reaction was checked by TLC point plate, and then the solvent and excess oxalyl chloride were removed at low temperature under reduced pressure on a rotary evaporator to give dehydrocholic acid A-1 derived acid chloride. Then N- (2- (chloromethyl) -4-chlorophenyl) -4-methylbenzenesulfonamide B-4(329mg, 1.0mmol), dichloromethane (5mL), triphenylphosphine (288.6mg, 1.1mmol) and cesium hydroxide monohydrate (419.6mg, 2.5 mmol) were added to the above-obtained acid chloride, and the mixture was left to react at room temperature for 72 hours, and detected by TLC dot plate chromatography, the reaction system was separated and purified by column chromatography to obtain the objective compound I-4 as a white solid with a yield of 55%.
Example 5
A method for the synthesis of (8R, 9S, 10S, 13R, 14S, 17R) -10, 13-dimethyl-17- ((R) -4- (6-chloro-1-tosyl-1H-indol-2-yl) butandin-2-yl) dodecyl-3H-cyclopenta [ a ] phenanthrene-3, 7,12(2H, 4H) -trione comprising the following experimental steps:
dehydrocholic acid A-1(1.2mmol,483.1mg), dichloromethane (3mL), oxalyl chloride (3.6mmol,453.3mg), N, N-dimethylformamide (0.06mmol,4.3mg) were added to 10mL Schlenk flash at room temperature, the system was left to react at room temperature for 1 hour, the end of the reaction was checked by TLC point plate, and then the solvent and excess oxalyl chloride were removed at low temperature under reduced pressure on a rotary evaporator to give dehydrocholic acid A-1 derived acid chloride. Then N- (2- (chloromethyl) -3-chlorophenyl) -4-methylbenzenesulfonamide B-5(329mg, 1.0mmol), dichloromethane (5mL), triphenylphosphine (288.6mg, 1.1mmol) and cesium hydroxide monohydrate (419.6mg, 2.5 mmol) were added to the above-obtained acid chloride, and the mixture was left to react at room temperature for 72 hours, and detected by TLC dot plate chromatography, the reaction system was separated and purified by column chromatography to obtain the objective compound I-5 as a white solid with a yield of 55%.
Reference throughout this specification to "some embodiments," "particular implementations," or the like means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in one or more embodiments or examples of the present invention. The particular features, structures, materials, or characteristics described in this specification may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, various embodiments or examples and features of different embodiments or examples described in this specification can be combined and combined by one skilled in the art without contradiction.
Although embodiments of the present invention have been shown and described above, it is understood that the above embodiments are exemplary and should not be construed as limiting the present invention, and that variations, modifications, substitutions and alterations can be made to the above embodiments by those of ordinary skill in the art within the scope of the present invention.
Claims (9)
1. The diterpenoid anti-inflammatory compound containing the indole skeleton is characterized by being a compound shown as a formula I, and having a structure shown as follows:
wherein R is1Selected from hydrogen, halogen or methoxy, wherein R1The positions and the number of the (C) can be unfixed.
2. The anti-inflammatory diterpenoid compound having an indole skeleton according to claim 1, wherein the compound further comprises a pharmaceutically acceptable salt, a crystalline hydrate or a solvate.
3. A diterpenoid anti-inflammatory compound having an indole skeleton according to claim 2, wherein the halogen comprises chlorine or bromine.
4. The diterpenoid anti-inflammatory compound having an indole skeleton according to claim 3, wherein the compound represented by the formula I comprisesAny one of (1):
5. method for preparing diterpenoid anti-inflammatory compounds containing an indole skeleton according to claim 1, characterized in that the synthetic route is as follows:
(1) adding a compound shown as a formula A, a solvent, oxalyl chloride and N, N-dimethylformamide into a reaction bottle at normal temperature, uniformly stirring at room temperature for reaction, and detecting the reaction end point by TLC;
(2) carrying out decompression spin-drying on the reaction product obtained in the step (1);
(3) adding a compound shown in the formula B, a solvent, triphenylphosphine and alkali into the product obtained in the step (2), placing the reaction system at room temperature, uniformly stirring for reaction, and detecting the reaction end point by TLC (thin layer chromatography);
(4) separating and purifying the reaction system in the step (3) to obtain a target compound shown in a formula I;
in the above compound, wherein R1Selected from hydrogen, or methoxy, wherein R1The position and the number of the halogen can be not fixed, and the halogen is selected from chlorine or bromine.
6. The method for preparing diterpenoid anti-inflammatory compounds having an indole skeleton according to claim 5, wherein: the molar charge ratio of the compound shown in the formula A, the oxalyl chloride, the N, N-dimethylformamide, the compound shown in the formula B and the triphenylphosphine in the steps (1) and (3) is 1.1-1.3:3-4:0.05-0.15:1: 1.1-1.2.
7. The method for preparing diterpenoid anti-inflammatory compounds having an indole skeleton according to claim 5, wherein: the solvent in the steps (1) and (3) is selected from dichloromethane, tetrahydrofuran or diethyl ether.
8. The method for preparing diterpenoid anti-inflammatory compounds having an indole skeleton according to claim 5, wherein: the base in the step (3) is selected from cesium hydroxide monohydrate, cesium carbonate or triethylamine.
9. The method for preparing diterpenoid anti-inflammatory compounds having an indole skeleton according to claim 5, wherein: the feeding sequence of the step (3) is a compound shown as a formula B, dichloromethane, triphenylphosphine, cesium hydroxide monohydrate and the system obtained in the step (2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010208332.4A CN113429450A (en) | 2020-03-23 | 2020-03-23 | Diterpenoid anti-inflammatory compound containing indole skeleton and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010208332.4A CN113429450A (en) | 2020-03-23 | 2020-03-23 | Diterpenoid anti-inflammatory compound containing indole skeleton and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113429450A true CN113429450A (en) | 2021-09-24 |
Family
ID=77752616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010208332.4A Pending CN113429450A (en) | 2020-03-23 | 2020-03-23 | Diterpenoid anti-inflammatory compound containing indole skeleton and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113429450A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101416959A (en) * | 2008-12-15 | 2009-04-29 | 郑州大学 | Use of 15-methano-substituted-andrographolide derivative in preparing anti-inflammatory ntipyretic analgesic medicine |
| CN101481401A (en) * | 2008-04-10 | 2009-07-15 | 中国科学院上海药物研究所 | Tripterygium wilfordii diterpenoid lactone derivative, pharmaceutical composition thereof and use in genital system tumor resistance |
-
2020
- 2020-03-23 CN CN202010208332.4A patent/CN113429450A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481401A (en) * | 2008-04-10 | 2009-07-15 | 中国科学院上海药物研究所 | Tripterygium wilfordii diterpenoid lactone derivative, pharmaceutical composition thereof and use in genital system tumor resistance |
| CN101416959A (en) * | 2008-12-15 | 2009-04-29 | 郑州大学 | Use of 15-methano-substituted-andrographolide derivative in preparing anti-inflammatory ntipyretic analgesic medicine |
Non-Patent Citations (1)
| Title |
|---|
| TING-BI HUA等: "Tandem Phospha-Michael Addition/N-Acylation/ Intramolecular Wittig Reaction of aza-o-Quinone Methides: Approaches to 2, 3-Disubstituted Indoles", 《ADVANCED SYNTHESIS & CATALYSIS》, vol. 362, no. 13, pages 2615 - 2619 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107382820B (en) | Synthetic method of 3-aryl isoindole derivative | |
| Kashinath et al. | Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes | |
| SU1547707A3 (en) | Method of producing trans-ethyl-1,2,3,4-tetrahydro-6,7-methylenedioxy-4-oxo-1(3,4,5-trimethylyl)naphthalene-2-carboxylate | |
| CN113429450A (en) | Diterpenoid anti-inflammatory compound containing indole skeleton and preparation method thereof | |
| CN106892800A (en) | A kind of preparation method and application of unactivated alkene hydrogen trifluoromethylation | |
| WO1997000850A1 (en) | Process for producing 2-(halomethyl)phenylacetic acid esters | |
| CN115197058B (en) | Anticancer natural product Dysideanone B analogue and preparation method thereof | |
| Matsumoto et al. | High-pressure aminolysis of lactones to hydroxy amides. | |
| CN111285792B (en) | 2-substituted indole compound and preparation method thereof | |
| CN112624957A (en) | Synthetic method of 3-alkyl isoindolinone derivatives | |
| CN109761993B (en) | Spirobenzofuran-3, 3' -quinoline derivative and synthesis method and application thereof | |
| CN101287705A (en) | Synthesis of 1alpha-fluoro-25-hydroxy-16-23e-diene-26,27-bishomo-20-epi-cholecalciferol | |
| Yuan et al. | Facile synthesis of CF3-substituted dienamides via one-pot tandem reactions | |
| CN111499600A (en) | Synthesis method of polysubstituted 2, 3-dihydrofuran compound | |
| CN113372298B (en) | Preparation method of 2-iodine-3-amino naphthoquinone compound | |
| WO1991003460A1 (en) | New route of synthesis for tertiary alkyl esters | |
| CN110204456B (en) | Polysubstituted naphthalene derivative and synthesis method thereof | |
| CN108299445B (en) | Synthesis method of 1, 5-azaspiro [2,4] heptane | |
| CN117986274A (en) | Hexahexabenzofuran derivative and synthetic method and application thereof | |
| SU780435A1 (en) | 3,4-dihydro-10oxy-1(2h)-phenanthrenones as semi-product in synthesis of steroids or their analogues and method of obtaining same | |
| JPH10251190A (en) | Aromatic ketone compound, its production and intermediate thereof | |
| JP2701411B2 (en) | 3-Phenoxycyclopentene derivative, method for producing the same and method for producing cyclopenta [b] benzofuran derivative from the compound | |
| Hernández-Calva et al. | Halogenation of Aldoximes. A Versatile Reaction for the Synthesis of Highly Functionalized Hydroximoyl Chlorides and Furazan N-Oxides | |
| JP4219289B2 (en) | Polycyclic ketone compound and process for producing the same | |
| JP4253603B2 (en) | Polycyclic compound and method for producing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |