CN103553858A - Triarylmethane compound containing azulene-type structure and preparation method thereof - Google Patents

Triarylmethane compound containing azulene-type structure and preparation method thereof Download PDF

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CN103553858A
CN103553858A CN201310539145.4A CN201310539145A CN103553858A CN 103553858 A CN103553858 A CN 103553858A CN 201310539145 A CN201310539145 A CN 201310539145A CN 103553858 A CN103553858 A CN 103553858A
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azulene
hydroxyl
triaryl methane
methane compounds
structure according
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王道林
赵伟
石晓策
董哲
马健
冯姗姗
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Bohai University
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Abstract

The invention discloses a triarylmethane compound containing an azulene-type structure and a preparation method thereof. The triarylmethane compound has a structural general formula as shown in the specification. The method is characterized in that 2-azulene hydroxyl-1-ethyl formate and aromatic aldehyde are adopted as reaction raw materials and have condensation reaction under the effect of a catalyst, and a reaction product is purified to obtain a target product. The triarylmethane compound containing the azulene-type structure is easy to derivate, has multiple reaction points, is suitable for the molecule diversity research and can be selectively synthesized into a polycyclic compound.

Description

Contain triaryl methane compounds of azulene structure and preparation method thereof
Technical field
The present invention relates to triaryl methane compounds, say more specifically a kind of triarylmethane compounds containing azulene structure and preparation method thereof.
Background technology
Triarylmethane compounds is extensively present in natural product, is the important feature skeleton of functional compound.
Triarylmethane compounds has good medicine dynamically and kinetic property; this compounds that contains multiple novel structure type is synthesized and is applied to pharmacology activity research; as bioactive compounds and aspect medicament research and development, show excellent activity, as: anti-inflammatory (Lacroix, R.; Poupelin, J.P.; Lacroix, J.; Reynouard, F.; Ombescot, C.Ann.Pharm.Fr., 1979,37,131-134), antimycotic (Podder, S.; Choudhury.J.; Roy, U.K.; Roy, S.J.Org.Chem., 2007,72,3100-3103), antitumor (Masatoshi, Y.; Kuniko, H.; Yoshiko, Y.; Junko, S.; Richard, F.; Luduena, R.F.; Asok, B.; Shigeru, T.; Tazuko, T.; Takashi, T.J.Med.Chem., 1987,30,1897-1900), antiviral (Mibu, N.; Yokomizo, K.; Uyeda, M.; Sumoto, K.Chem.Pharm.Bull., 2005,53,1171-1174), tuberculosis (Parai, M.K.; Panda, G.; Chaturvedi, V.; Manju, Y.K.; Sinha, S.Bioorg.Med.Chem.Lett., 2008,18, the effect such as 289-292).
After azulenoid in 1863 is found, be just subject to extensive concern, because of its unique chemical structure and the distinctive physics, chemistry and the biological activity that show, in a plurality of fields, all play an important role.
At field of medicaments, the effects such as the anti-inflammatory that azulenoid shows (JP:55-129241), anticancer (JP:61-161290) and antiulcer agent (JP:61-180761); Can be used for treating eyes and pericementitis (JP:10-182546) and the cardiovascular disorder (JP:10-182546) of clinical middle appearance, also available its cured the illnesss such as neural deterioration (US:5843999) and nervous disorders.At chemical field, can be used for Laser Printing and xerox (US:20030129516), also can be used as dyestuff, liquid-crystal display (JP:2069437), sight sensor (US:4990649) etc.At cosmetic field, azulenoid also shows the effects such as good moisturizing, moisturizing and crease-resistant (JP:5178716).
Summary of the invention
The present invention is intended to overcome the deficiencies in the prior art part and a kind of derivatize that is easy to is provided, and has a plurality of reflecting points, is applicable to triaryl methane compounds containing azulene structure of molecular diversity research alternative synthetic polycyclic compound and preparation method thereof.
For solving the problems of the technologies described above, the present invention is achieved in that
A triaryl methane compounds that contains azulene structure, has following general structure:
Figure BDA0000406924060000021
The method of preparing the above-mentioned triaryl methane compounds that contains azulene structure, it take 2-hydroxyl Azulene-1-ethyl formate and aromatic aldehyde is reaction raw materials, carries out condensation reaction under catalyst action, purified processing, obtains object product.
As a kind of preferred version, aromatic aldehyde of the present invention is the compound with following general structure:
Figure BDA0000406924060000022
Wherein, R is one or more the mixture in H, methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, alkoxyl group, hydroxyl, halogen, nitro, cyano group and carbalkoxy substituting group.
Further, aromatic aldehyde of the present invention can be selected heteroaromatic aldehyde.
Further, heteroaromatic aldehyde of the present invention can select to there is furans, the aromatic aldehyde of thiophene, pyrroles or pyridine heterocycle structure.
Further, catalyzer of the present invention is sulfuric acid, phosphoric acid, phospho-wolframic acid, methylsulphonic acid or p-methyl benzenesulfonic acid.
Further, catalyzer of the present invention is methylsulphonic acid or p-methyl benzenesulfonic acid.
Further, the mol ratio of aromatic aldehyde of the present invention and 2-hydroxyl Azulene-1-ethyl formate is 1:1～4.
Further, the mol ratio of aromatic aldehyde of the present invention and 2-hydroxyl Azulene-1-ethyl formate is 1:1～3.5.
Composition principle of the present invention is:
Figure BDA0000406924060000031
Take 2-hydroxyl Azulene-1-ethyl formate and aromatic aldehyde is raw material, under catalyst action, carry out condensation reaction, according to ordinary method, carries out purification process.
The chemical structure of 2-hydroxyl Azulene-1-ethyl formate is as follows:
Can prepare according to literature method (as, Tetsuo, N.; Kahei, T.; Noboru, S.the15 thannual Meeting of the Chemical Society of Japan, 1964,37,1644-1648).
Aromatic aldehyde is the compound with following general structure:
Wherein, R is a kind of in the substituting groups such as H, methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, alkoxyl group, hydroxyl, halogen, nitro, cyano group, carbalkoxy.Can buy from market or according to literature method preparation (as, Organic Syntheses, 2005, Vol.82, p.64-68; 2009, Coll.Vol.11, p.267-271).
Aromatic aldehyde comprises the aromatic aldehyde of heterocycle structures such as containing furans, thiophene, pyrroles, pyridine.
Catalyzer is sulfuric acid, phosphoric acid, phospho-wolframic acid, methylsulphonic acid, p-methyl benzenesulfonic acid etc., is preferably methylsulphonic acid, p-methyl benzenesulfonic acid.
Reaction can be at methyl alcohol, ethanol, and Virahol, butanols, acetonitrile, ethyl acetate, DMF, carries out in dimethyl sulfoxide (DMSO) equal solvent.
The compounds of this invention is easy to derivatize, has a plurality of reflecting points, and its synthetic method is simple and direct, can synthesize a large amount of compound libraries at short notice, is applicable to the molecular diversity research of compound.Simultaneously, because triarylmethane compounds has good medicine dynamically and kinetic property, as bioactive compounds and aspect medicament research and development, show excellent activity, the present invention can be used as clinical medicine and lead compound thereof, for having the high flux screening of potential drug or bioactive compounds, has opened up wide application prospect.
Embodiment
The present invention will be described further with embodiment below, but content of the present invention is not subject to the restriction of this embodiment.
Embodiment 1
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) phenylmethane
By 2-hydroxyl Azulene-1-ethyl formate (475mg, 2.2mmol), p-methyl benzenesulfonic acid (35mg) is dissolved in ethanol (25mL), stirs it is fully dissolved, and in solution, drips phenyl aldehyde (106mg, 1.0mmol).Reflux 30min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) phenylmethane, red crystallization, yield 91%.
Structural analysis is as follows:
Figure BDA0000406924060000051
7.40-7.43(5H,m),8.46(2H,d,J=10.4Hz),8.93(2H,d,J=9.2Hz),11.13(2H,s,OH)。
Ultimate analysis: C 33h 28o 6measured value (theoretical value), C76.32(76.14), H5.55(5.42) %.
Embodiment 2
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-aminomethyl phenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (475mg, 2.2mmol), p-methyl benzenesulfonic acid (35mg) is dissolved in methyl alcohol (20mL), stirs it is fully dissolved, and in solution, drips 4-tolyl aldehyde (120mg, 1.0mmol).Reflux 35min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-aminomethyl phenyl) methane, red crystallization, yield 94%.
Structural analysis is as follows:
Figure BDA0000406924060000052
=7.2Hz,CO 2 CH 2CH 3),6.71(1H,s),7.05-7.06(4H,m),7.37-7.41(2H,m),7.44-7.47(4H,m),8.48(2H,d,J=10.4Hz),8.93(2H,d,J=9.6Hz),11.14(2H,s,OH)。
Ultimate analysis: C 34h 30o 6measured value (theoretical value), C76.57(76.39), H5.83(5.66) %.
Embodiment 3
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-p-methoxy-phenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (518mg, 2.4mmol), p-methyl benzenesulfonic acid (40mg) is dissolved in methyl alcohol (40mL), stirs it is fully dissolved, and in solution, drips 4-methoxybenzaldehyde (136mg, 1.0mmol).Reflux 25min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-p-methoxy-phenyl) methane, red crystallization, yield 90%.
Structural analysis is as follows:
Figure BDA0000406924060000061
Hz),6.98(2H,d,J=8.2Hz),7.36-7.38(2H,m),7.55-7.58(4H,m),8.31(2H,d,J=10.4Hz),8.98(2H,d,J=10.0Hz),10.92(2H,s,OH)。
Ultimate analysis: C 34h 30o 7measured value (theoretical value), C74.28(74.17), H5.61(5.49) %.
Embodiment 4
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-chloro-phenyl-) methane
By 2-hydroxyl Azulene-1-ethyl formate (518mg, 2.4mmol), methylsulphonic acid (30mg) is dissolved in methyl alcohol (40mL), stirs it is fully dissolved, and in solution, drips 4-chlorobenzaldehyde (140mg, 1.0mmol).Reflux 45min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-chloro-phenyl-) methane, red crystallization, yield 90%.Structural analysis is as follows:
=8.4Hz),7.30-7.33(2H,m),7.41-7.47(4H,m),8.45(2H,d,J=10.0Hz),8.94(2H,d,J=9.2Hz),11.16(2H,s,OH)。
Ultimate analysis: C 33h 27clO 6measured value (theoretical value), C71.57(71.41), H5.13(4.90) %.
Embodiment 5
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-fluorophenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (540mg, 2.5mmol), methylsulphonic acid (30mg) is dissolved in methyl alcohol (40mL), stir it is fully dissolved, in solution, drip 4-fluorobenzaldehyde (124mg, 1.0mmol).Reflux 50min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-fluorophenyl) methane, red crystallization, yield 88%.Structural analysis is as follows:
Figure BDA0000406924060000072
=8.8Hz),7.34(2H,dd,J=9.2,9.6Hz),7.38-7.42(4H,m),8.38(2H,d,J=10.4Hz),8.88(2H,d,J=9.6Hz),11.09(2H,s,OH)。
Ultimate analysis: C 33h 27fO 6measured value (theoretical value), C73.73(73.59), H5.22(5.05) %.
Embodiment 6
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-hydroxy phenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (518mg, 2.4mmol), p-methyl benzenesulfonic acid (50mg) is dissolved in ethanol (40mL), stirs it is fully dissolved, and in solution, drips 4-hydroxy benzaldehyde (122mg, 1.0mmol).Reflux 25min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-hydroxy phenyl) methane, red crystallization,
Yield 94%.
Structural analysis is as follows:
Figure BDA0000406924060000081
=7.6Hz),7.01-7.04(2H,m),7.38-7.44(4H,m),8.45(2H,d,J=9.6Hz),8.92(2H,d,J=9.6Hz),11.11(2H,s,OH)。
Ultimate analysis: C 33h 28o 7measured value (theoretical value), C74.03(73.87), H5.43(5.26) %.
Embodiment 7
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (2-p-methoxy-phenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (561mg, 2.6mmol), p-methyl benzenesulfonic acid (40mg) is dissolved in ethanol (40mL), stirs it is fully dissolved, and in solution, drips Benzaldehyde,2-methoxy (136mg, 1.0mmol).Reflux 60min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (2-p-methoxy-phenyl) methane, red crystallization, yield 84%.
Structural analysis is as follows:
Figure BDA0000406924060000091
m),7.19-7.24(3H,m),7.33-7.42(5H,m),8.30(2H,d,J=10.4Hz),8.92(2H,d,J=9.4Hz),11.01(2H,s,OH)。
Ultimate analysis: C 34h 30o 7measured value (theoretical value), C74.32(74.17), H5.64(5.49) %.
Embodiment 8
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (2-hydroxy phenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (540mg, 2.5mmol), methylsulphonic acid (30mg) is dissolved in ethanol (40mL), stirs it is fully dissolved, and in solution, drips salicylic aldehyde (122mg, 1.0mmol).Reflux 45min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (2-hydroxy phenyl) methane, red crystallization, yield 85%.
Structural analysis is as follows:
Figure BDA0000406924060000092
7.17-7.23(1H,m),7.27-7.31(2H,m),7.42-7.46(4H,m),8.38(2H,d,J=10.0Hz),8.95(2H,d,J=9.2Hz),11.07(2H,s,OH)。
Ultimate analysis: C 33h 28o 7measured value (theoretical value), C73.98(73.87), H5.45(5.26) %.
Embodiment 9
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (2,4-Dimethoxyphenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (475mg, 2.2mmol), p-methyl benzenesulfonic acid (40mg) is dissolved in acetonitrile (40mL), stirs it is fully dissolved, and in solution, drips 2,4-dimethoxy benzaldehyde (166mg, 1.0mmol).Reflux 40min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (2,4-Dimethoxyphenyl) methane, red crystallization, yield 89%.
Structural analysis is as follows:
Figure BDA0000406924060000101
=7.2Hz),6.45(1H,s),6.66(1H,s),6.82(1H,d,J=7.0Hz),7.19-7.24(2H,m),7.35-7.39(4H,m),8.23(2H,d,J=10.2Hz),8.89(2H,d,J=9.2Hz),10.98(2H,s,OH)。
Ultimate analysis: C 35h 32o 8measured value (theoretical value), C72.61(72.40), H5.62(5.56) %.
Embodiment 10
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (3,4-Dimethoxyphenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (475mg, 2.2mmol), methylsulphonic acid (20mg) is dissolved in acetonitrile (40mL), stirs it is fully dissolved, and in solution, drips Veratraldehyde (166mg, 1.0mmol).Reflux 40min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (3,4-Dimethoxyphenyl) methane, red crystallization, yield 92%.
Structural analysis is as follows:
Figure BDA0000406924060000111
m),6.70-6.72(1H,m),6.78(1H,s),7.27-7.30(3H,m),7.39-7.45(4H,m),8.23(2H,d,J=10.0Hz),8.93(2H,d,J=9.6Hz),11.11(2H,s,OH)。
Ultimate analysis: C 35h 32o 8measured value (theoretical value), C72.52(72.40), H5.67(5.56) %.
Embodiment 11
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (3-methoxyl group-4-hydroxy phenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (540mg, 2.5mmol), methylsulphonic acid (20mg) is dissolved in to N, in N-diformamide (30mL), stirring is fully dissolved it, in solution, drips Vanillin (152mg, 1.0mmol).Reflux 30min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (3-methoxyl group-4-hydroxy phenyl) methane, red crystallization, yield 94%.
Structural analysis is as follows:
Figure BDA0000406924060000112
6.59-6.61(1H,m),6.68(1H,s),6.76-6.78(2H,m),7.23-7.24(2H,m),7.38-7.41(4H,m),8.45(2H,d,J=10.4Hz),8.92(2H,d,J=9.2Hz),11.12(2H,s,OH)。
Ultimate analysis: C 34h 30o 8measured value (theoretical value), C72.14(72.07), H5.50(5.34) %.
Embodiment 12
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-nitrophenyl) methane
By 2-hydroxyl Azulene-1-ethyl formate (648mg, 3.0mmol), methylsulphonic acid (50mg) is dissolved in DMF (30mL), stirs it is fully dissolved, and in solution, drips 4-nitrobenzaldehyde (151mg, 1.0mmol).Reflux 80min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (4-nitrophenyl) methane, red crystallization, yield 82%.
Structural analysis is as follows:
=8.8Hz),7.27(2H,d,J=8.2Hz),7.28-7.29(2H,m),7.37-7.43(4H,m),8.02(2H,d,J=8.2Hz),8.39(2H,d,J=10.4Hz),8.89(2H,d,J=9.2Hz),11.16(2H,s,OH).
Ultimate analysis: C 33h 27nO 8measured value (theoretical value), C70.16(70.08), H4.97(4.81) N2.67 (2.48) %.
Embodiment 13
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (furans-2-yl) methane
By 2-hydroxyl Azulene-1-ethyl formate (756mg, 3.5mmol), p-methyl benzenesulfonic acid (40mg) is dissolved in acetonitrile (40mL), stirs it is fully dissolved, and in solution, drips furfural (96mg, 1.0mmol).Reflux 65min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (furans-2-yl) methane, red crystallization, yield 73%.
Structural analysis is as follows:
7.18-7.33(7H,m),8.51(2H,d,J=10.0Hz),8.90(2H,d,J=9.6Hz),11.06(2H,s,OH)。
Ultimate analysis: C 31h 26o 7measured value (theoretical value), C73.14(72.93), H5.26(5.13) %.
Embodiment 14
Synthesizing of two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (thiophene-2-yl) methane
By 2-hydroxyl Azulene-1-ethyl formate (648mg, 3.0mmol), p-methyl benzenesulfonic acid (30mg) is dissolved in acetonitrile (40mL), stirs it is fully dissolved, and in solution, drips thiophene-2-formaldehyde (112mg, 1.0mmol).Reflux 50min(thin-layer chromatography is followed the tracks of reaction), be cooled to after room temperature, through decompress filter, with ethanol, wash, obtain two (2-hydroxyl-3-ethoxycarbonyl Azulene-1-yl) (thiophene-2-yl) methane, red crystallization, yield 85%.
Structural analysis is as follows:
7.17-7.19(1H,m),7.31-7.38(2H,m),7.41-7.50(4H,m),8.59(2H,d,J=10.2Hz),8.94(2H,d,J=9.6Hz),11.20(2H,s,OH)。
Ultimate analysis: C 31h 26o 6s measured value (theoretical value), C70.84(70.71), H5.16(4.98) %.
Be understandably, above about specific descriptions of the present invention, only for the present invention is described, and be not limited to the described technical scheme of the invention process example, those of ordinary skill in the art is to be understood that, still can modify or be equal to replacement the present invention, to reach identical technique effect; As long as meet, use needs, all within protection scope of the present invention.

Claims (9)

1. a triaryl methane compounds that contains azulene structure, is characterized in that, has following general structure:
Figure FDA0000406924050000011
2. a method of preparing the triaryl methane compounds that contains as claimed in claim 1 azulene structure, it is characterized in that: take 2-hydroxyl Azulene-1-ethyl formate and aromatic aldehyde is reaction raw materials, under catalyst action, carry out condensation reaction, purified processing, obtains object product.
3. the method for the triaryl methane compounds that preparation contains azulene structure according to claim 2, is characterized in that: described aromatic aldehyde is the compound with following general structure:
Figure FDA0000406924050000012
Wherein, R is one or more the mixture in H, methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, alkoxyl group, hydroxyl, halogen, nitro, cyano group and carbalkoxy substituting group.
4. the method for the triaryl methane compounds that preparation contains azulene structure according to claim 2, is characterized in that: described aromatic aldehyde is heteroaromatic aldehyde.
5. the method for the triaryl methane compounds that preparation contains azulene structure according to claim 4, is characterized in that: described heteroaromatic aldehyde is the aromatic aldehyde with furans, thiophene, pyrroles or pyridine heterocycle structure.
6. the method for the triaryl methane compounds that contains azulene structure according to the arbitrary described preparation of claim 2～5, is characterized in that: described catalyzer is sulfuric acid, phosphoric acid, phospho-wolframic acid, methylsulphonic acid or p-methyl benzenesulfonic acid.
7. the method for the triaryl methane compounds that preparation contains azulene structure according to claim 6, is characterized in that: described catalyzer is methylsulphonic acid or p-methyl benzenesulfonic acid.
8. the method for the triaryl methane compounds that preparation contains azulene structure according to claim 6, is characterized in that: the mol ratio of described aromatic aldehyde and 2-hydroxyl Azulene-1-ethyl formate is 1:1～4.
9. the method for the triaryl methane compounds that preparation contains azulene structure according to claim 8, is characterized in that: the mol ratio of described aromatic aldehyde and 2-hydroxyl Azulene-1-ethyl formate is 1:1～3.5.
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CN108250080A (en) * 2018-03-20 2018-07-06 黑龙江中医药大学 Containing azulene structure triaryl methane compounds, preparation method and its as the application in anti-oxidizing activities or antitumor drug

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