CN105859619B - The method of the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines - Google Patents
The method of the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines Download PDFInfo
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- CN105859619B CN105859619B CN201610314178.2A CN201610314178A CN105859619B CN 105859619 B CN105859619 B CN 105859619B CN 201610314178 A CN201610314178 A CN 201610314178A CN 105859619 B CN105859619 B CN 105859619B
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- ionic liquid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0279—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the cationic portion being acyclic or nitrogen being a substituent on a ring
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Abstract
The invention discloses a kind of synthetic methods of the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines, with aromatic aldehyde compound, 5,5- dimethyl -1, hydroresorcinol and ammonium acetate are substrate, betaines ionic liquid is catalyst, ethyl alcohol is solvent, and acridine cyclohexadione compounds are made in heating reflux reaction, and wherein the cation of betaines ionic liquid is, anion CH3COO‑、C2H5COO‑、CH3CHOHCOO‑Or H2PO4 ‑.Betaines ionic liquid of the invention has good catalytic activity under relatively mild conditions, and its catalytic activity is held essentially constant after being recycled repeatedly, the operation of this catalyst system and last handling process are simple, only the acridine cyclohexadione compounds of high-purity need to can be obtained by simply washing or recrystallizing.
Description
Technical field
The invention belongs to the synthesis technical fields of ionic liquid-catalyzed synthesis acridine cyclohexadione compounds, and in particular to a kind of
The synthetic method of the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines.
Background technique
Acridine diketone is a kind of important heterocyclic compound, they have many use in terms of materia medica, such as killing
Microbial inoculum, antimalarial, antitumor, antimicrobial and fungicide etc..Therefore, many drug research persons to such compound very
It is interested.In addition, their derivative also acts as laser dye and photoinitiator.Currently, scientists are also researching and developing
They are used for laser technology by this compound.Multi-component Hantzsch reaction is a kind of effective synthesis acridine diketone
Method usually uses aldehyde, dimetone and urea, aminomethane, aniline, ammonium acetate etc. anti-to carry out as raw material containing nitrogen compound
It answers.So far, it has been reported that the catalyst for the synthesis acridine diketone crossed is various, such as: macroreticular resin -15(Kaya
M, Yildirir Y, Celik G Y. Synthesis and antimicrobial activities of novel
bisacridine-1,8-dione derivatives [J]. Med. Chem. Res., 2011, 20:293–
299.), SiO2Polyphosphoric acids (Nasresfahani Z, the Kassaee M Z. Mesoporous silica of support
nanoparticles in an efficient, solvent-free, green synthesis of
Acridinediones [J] Catalysis Communications, 2015,60: 100-104.), CdO nano particle
(Borhade A V, Uphade B K, Gadhave AG. Efficient, solvent-free synthesis of
acridinediones catalyzed by CdO nanoparticles [J]. Research on Chemical
Intermediates, 2015,41 (3): 1447-1458.), ammonium ceric nitrate (CAN) (Kidwai M, Bhatnagar D.
Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted
decahydroacridine-1,8-diones in PEG [J]. Tetrahedron Letters, 2010,51: 2700–
2703.), glyoxaline ion liquid (Palani K, Thirumalai D, the Ambalavanan P, et of Br nsted acidity
al. Synthesis and characterization of 9-(4-nitrophenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydro-1,8(2H,5H) acridinedione and its methoxyphenyl
Derivative [J] Journal of Chemical Crystallography, 2005,35 (10): 751-760.), three
(Wang Xiangshan, Shi Daqing, Zhang Yanfei wait triethyl benzyl ammonia chloride (TEBA) catalysis to be lauched middle 9- to ethylbenzylammonium chloride
Synthesis [J] Chin. J. Org. Chem. of the more hydrogen acridine derivatives of aryl, 2004,24 (4): 430-432.), sulfonic acid
The SiO of change2(Seyyedhamzeh M, Mirzaei P, Bazgir A. Solvent-free synthesis of aryl-
14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica
Sulfuric acid as catalyst [J] Dyes and Pigments, 2008,76:836-839.), Zn (OAc)2-
2H2O or proline (Venkatesan K, Pujari S S, Srinivasan K V. Proline-Catalyzed
Simple and Efficient Synthesis of 1,8-Dioxo-decahydroacridines in Aqueous
Ethanol Medium [J] Synthetic Communicatin, 2009,39 (2): 228-241.) and cetyl three
Methyl bromide ammonium (CTAB) (Xia J J, Zhang K H. Synthesis ofN-substituted
Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water [J].
Molecules, 2012,17,5339-5345.) etc..It needs to add however, these catalyst systems often have the disadvantage in that
Toxic solvent；Reaction time is longer；Catalyst preparation is cumbersome and expensive, cannot reuse.In consideration of it, exploitation one
The synthetic method of kind effectively, green, economic is a problem to be solved to prepare acridine cyclohexadione compounds.
Nearest decades, ionic liquid cause science and industry as a kind of novel green catalyst and solvent
Extensive concern.Ionic liquid type, which is enriched and can be made to measure according to specific needs, often assigns some spies by people
Different function is expected to be applied to more research fields, wide application prospect is especially shown in synthesis and catalytic industries.
At present still not about the synthesis acridine cyclohexadione compounds using betaines ionic liquid as catalyst multi-component reaction
Relevant report.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of ionic liquid-catalyzed multi-component reactions of betaines to synthesize a word used for translation
The synthetic method of pyridine cyclohexadione compounds, this method is using betaines ionic liquid cheap and easy to get and convenience and high-efficiency as catalysis
Agent, efficient catalytic multi-component reaction synthesizes acridine cyclohexadione compounds under mild conditions.
The present invention adopts the following technical scheme that the ionic liquid-catalyzed multicomponent of betaines is anti-to solve above-mentioned technical problem
The synthetic method of acridine cyclohexadione compounds should be synthesized, it is characterised in that: with aromatic aldehyde compound, 5,5- dimethyl -1,3-
Cyclohexanedione and ammonium acetate are substrate, and betaines ionic liquid is catalyst, and ethyl alcohol is solvent, and a word used for translation is made in heating reflux reaction
Pyridine cyclohexadione compounds, wherein aromatic aldehyde compound be、、
Or, R H, 4-OH, 4-F, 4-Cl, 4-Br, 4-CH3、4-OCH3、4-CF3、4-NO2、3-NO2、
4-OH-3-OCH3, 2-Cl or 3-Cl, the cation of betaines ionic liquid be, anion is
CH3COO-、C2H5COO-、CH3CHOHCOO-Or H2PO4 -。
Further preferably, the aromatic aldehyde compound, dimethyl -1 5,5-, hydroresorcinol, ammonium acetate and beet
The molar ratio of ionic liquid is 1:2:1.5:0.05-1.
Further preferably, the betaines ionic liquid is to be led to by anhydrous betaine with corresponding inorganic acid or carboxylic acid
It crosses made from neutralization reaction.
Further preferably, the specific synthesis process of the acridine cyclohexadione compounds are as follows: successively add in the reaction vessel
Enter aromatic aldehyde compound, dimethyl -1 5,5-, hydroresorcinol, ammonium acetate, betaines ionic liquid and ethyl alcohol, then in
60 DEG C of heating reflux reactions are until TLC detects raw material fully reacting, after the mixed solution of last crude product water and ethyl alcohol washs
It dries and sterling acridine cyclohexadione compounds is made.
Further preferably, repetitive cycling uses after betaines ionic liquid recycling.
Compared with the prior art, the present invention has the following advantages:
1, the preparation of betaines ionic-liquid catalyst is easy, cheap and has good biocompatibility；
2, betaines ionic liquid has good catalytic activity under relatively mild conditions, and is recycled
Its catalytic activity is held essentially constant after repeatedly；
3, the reaction system is corrosion-free to equipment, to reaction vessel without particular/special requirement；
4, the operation of this catalyst system and last handling process are simple, need to only be can be obtained by simply washing or recrystallizing
The acridine cyclohexadione compounds of high-purity.
Specific embodiment
Above content of the invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on above content of the present invention belong to this hair
Bright range.
Embodiment 1
Sequentially added in round-bottomed flask benzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol (1mmol) and
Ammonium acetate (0.75mmol), stirs evenly, and then adds the second of acetato- liquid (0.15mmol) and 1mL of glycine betaine
Alcohol, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC until reacting terminates, finally by crude product water and
The mixed solution of ethyl alcohol is washed, then dries and sterling can be obtained, yield 90%.
Embodiment 2
4- nitrobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the acetate ion liquid of glycine betaine
The ethyl alcohol of (0.025mmol) and 1mL, later in 80 DEG C of back flow reaction 8h, entire reaction process is detected with TLC to be tied until reacting
Beam finally washs the mixture of crude product water and ethyl alcohol, then dries and sterling can be obtained, yield 85%.
Embodiment 3
3- nitrobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the propionic acid ionic liquid (0.25mmol) of glycine betaine
With the ethyl alcohol of 1mL, later in 80 DEG C of back flow reaction 8h, entire reaction process is detected with TLC to be terminated up to reacting, and finally will slightly be produced
The mixture of product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 85%.
Embodiment 4
4- bromobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the lactate ions liquid (0.5mmol) of glycine betaine
With the ethyl alcohol of 1mL, later in 80 DEG C of back flow reaction 5h, entire reaction process is detected with TLC to be terminated up to reacting, and finally will slightly be produced
The mixture of product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 90%.
Embodiment 5
4-methoxybenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the lactate ions liquid (0.15mmol) of glycine betaine
With the ethyl alcohol of 1mL, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC to be terminated up to reacting, and finally will slightly be produced
The mixture of product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 93%.
Embodiment 6
4- hydroxy benzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the lactate ions liquid (0.15mmol) of glycine betaine
With the ethyl alcohol of 1mL, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC to be terminated up to reacting, and finally will slightly be produced
The mixture of product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 90%.
Embodiment 7
4- tolyl aldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the lactate ions liquid (0.15mmol) of glycine betaine
With the ethyl alcohol of 1mL, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC to be terminated up to reacting, and finally will slightly be produced
The mixture of product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 90%.
Embodiment 8
4- trifluoromethylated benzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.15mmol) and 1mL, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC to be terminated up to reacting,
Finally the mixture of crude product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 95%.
Embodiment 9
4- chlorobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.05mmol) and 1mL, later in 80 DEG C of back flow reaction 3.5h, entire reaction process is detected with TLC to be tied until reacting
Beam finally washs the mixture of crude product water and ethyl alcohol, then dries and sterling can be obtained, yield 82%.
Embodiment 10
4- fluorobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.5mmol) and 1mL, later in 80 DEG C of back flow reaction 3.5h, entire reaction process is detected with TLC to be tied until reacting
Beam finally washs the mixture of crude product water and ethyl alcohol, then dries and sterling can be obtained, yield 90%.
Embodiment 11
3- chlorobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.15mmol) and 1mL, later in 80 DEG C of back flow reaction 3.5h, entire reaction process is detected with TLC to be tied until reacting
Beam finally washs the mixture of crude product water and ethyl alcohol, then dries and sterling can be obtained, yield 85%.
Embodiment 12
Sequentially added in round-bottomed flask vanillic aldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol (1mmol) and
Ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid (0.15mmol) and 1mL of glycine betaine
Ethyl alcohol, later in 80 DEG C of back flow reaction 8h, entire reaction process is detected with TLC until reacting terminates, and finally uses crude product
The mixture of water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 90%.
Embodiment 13
2- chlorobenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.15mmol) and 1mL, later in 80 DEG C of back flow reaction 6h, entire reaction process is detected with TLC to be terminated up to reacting,
Finally the mixture of crude product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 87%.
Embodiment 14
Sequentially added in round-bottomed flask cinnamic acid (0.5mmol), 5,5- dimethyl-hydroresorcinol (1mmol) and
Ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid (0.15mmol) and 1mL of glycine betaine
Ethyl alcohol, later in 80 DEG C of back flow reaction 1h, entire reaction process is detected with TLC until reacting terminates, and finally uses crude product
The mixture of water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 88%.
Embodiment 15
Pyridine-4-Carboxaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.15mmol) and 1mL, later in 80 DEG C of back flow reaction 1h, entire reaction process is detected with TLC to be terminated up to reacting,
Finally the mixture of crude product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 95%.
Embodiment 16
Furfural (0.5mmol), 5,5- dimethyl-hydroresorcinol (1mmol) and second are sequentially added in round-bottomed flask
Sour ammonium (0.75mmol), stir evenly, and then adds the biphosphate ionic liquid (0.15mmol) and 1mL of glycine betaine
Ethyl alcohol, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC until reacting terminates, finally by crude product water
It is washed with the mixture of ethyl alcohol, then dries and sterling can be obtained, yield 95%.
Embodiment 17
4-methoxybenzaldehyde (0.5mmol), 5,5- dimethyl-hydroresorcinol are sequentially added in round-bottomed flask
(1mmol) and ammonium acetate (0.75mmol), stirs evenly, and then adds the biphosphate ionic liquid of glycine betaine
The ethyl alcohol of (0.15mmol) and 1mL, later in 80 DEG C of back flow reaction 3h, entire reaction process is detected with TLC to be terminated up to reacting,
Finally the mixture of crude product water and ethyl alcohol is washed, then dries and sterling can be obtained, yield 96%.
Be probe reaction with embodiment 17, reacting coarse product after the washing of the mixed solution of water and ethyl alcohol, glycine betaine
Biphosphate ionic liquid stays in ethyl alcohol and aqueous solution, the biphosphate for the glycine betaine for then removing water and ethyl alcohol
Ionic liquid repetitive cycling uses.Do the active replica test of the biphosphate ionic liquid of catalyst glycine betaine, sweet tea
The biphosphate ionic liquid of dish alkali is reused 5 times, and product yield is shown in Table 1.
Situation is recycled in 1 Hydroxyl-functionalized Ionic Liquids of table
| Entry | Reaction time(h) | Yield(%) |
| 1 | 3 | 96 |
| 2 | 3 | 96 |
| 3 | 3 | 95 |
| 4 | 3 | 95 |
| 5 | 3 | 95 |
As can be seen from Table 1: the catalyst system of the biphosphate ionic liquid of glycine betaine prepares product in recycling
After being recycled 5 times in the process, yield is still very high, illustrates that the biphosphate ionic liquid of glycine betaine is catalyzing and synthesizing acridine
It can be recycled during dione compounds.
Embodiment above describes basic principles and main features of the invention and advantage, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe originals of the invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (5)
1. the synthetic method of the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines, feature exist
In: with aromatic aldehyde compound, dimethyl -1 5,5-, hydroresorcinol and ammonium acetate are substrate, and betaines ionic liquid is
Catalyst, ethyl alcohol are solvent, and acridine cyclohexadione compounds are made in heating reflux reaction, and wherein aromatic aldehyde compound is、、Or, R H, 4-OH, 4-
F、4-Cl、4-Br、4-CH3、4-OCH3、4-CF3、4-NO2、3-NO2、4-OH-3-OCH3, 2-Cl or 3-Cl, betaines ion
The cation of liquid is, anion CH3COO-、C2H5COO-、CH3CHOHCOO-Or H2PO4 -。
2. the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines according to claim 1
Synthetic method, it is characterised in that: the aromatic aldehyde compound, dimethyl -1 5,5-, hydroresorcinol, ammonium acetate and beet
The molar ratio of ionic liquid is 1:2:1.5:0.05-1.
3. the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines according to claim 1
Synthetic method, it is characterised in that: the betaines ionic liquid is by anhydrous betaine and corresponding inorganic acid or carboxylic acid
As made from neutralization reaction.
4. the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines according to claim 1
Synthetic method, it is characterised in that specific synthesis process are as follows: sequentially add aromatic aldehyde compound, 5,5- diformazan in the reaction vessel
Base -1, hydroresorcinol, ammonium acetate, betaines ionic liquid and ethyl alcohol, then in 60 DEG C of heating reflux reactions until TLC is examined
The mixed solution of survey raw material fully reacting, last crude product water and ethyl alcohol dries after washing and sterling acridine diones chemical combination is made
Object.
5. the ionic liquid-catalyzed multi-component reaction synthesis acridine cyclohexadione compounds of betaines according to claim 1
Synthetic method, it is characterised in that: repetitive cycling uses after the betaines ionic liquid recycling.
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| CN101914060A (en) * | 2010-03-16 | 2010-12-15 | 盐城师范学院 | Synthesizing of many hydrogen of degradable ionic liquid clean catalysis acridine derivatives |
| CN103193707A (en) * | 2013-04-18 | 2013-07-10 | 安徽工业大学 | Method for preparing 9-aryl multi-hydrogen acridine ramification through catalysis |
| CN105367535A (en) * | 2015-12-07 | 2016-03-02 | 安徽工业大学 | Green catalytic synthesis method of 1,8-dioxo-decahydroacridine derivative |
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| CN101914060A (en) * | 2010-03-16 | 2010-12-15 | 盐城师范学院 | Synthesizing of many hydrogen of degradable ionic liquid clean catalysis acridine derivatives |
| CN103193707A (en) * | 2013-04-18 | 2013-07-10 | 安徽工业大学 | Method for preparing 9-aryl multi-hydrogen acridine ramification through catalysis |
| CN105367535A (en) * | 2015-12-07 | 2016-03-02 | 安徽工业大学 | Green catalytic synthesis method of 1,8-dioxo-decahydroacridine derivative |
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| Methyltrioctylammonium chloride catalysed sonochemical synthesis of acridine diones;BHUPINDER KAUR，等;《J. Chem. Sci.》;20130930;第125卷(第5期);989-992，scheme1，实验部分 |
| 酸性离子液体催化合成9-芳基多氢吖啶衍生物;唐然肖,等;《化学研究与应用》;20070731;第19卷(第7期);809-812，实验部分，第2节 |
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