CN101139342A - Substituted triazole compound and synthesis method thereof - Google Patents
Substituted triazole compound and synthesis method thereof Download PDFInfo
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- CN101139342A CN101139342A CNA2007101334550A CN200710133455A CN101139342A CN 101139342 A CN101139342 A CN 101139342A CN A2007101334550 A CNA2007101334550 A CN A2007101334550A CN 200710133455 A CN200710133455 A CN 200710133455A CN 101139342 A CN101139342 A CN 101139342A
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- -1 triazole compound Chemical class 0.000 title claims abstract description 20
- 238000001308 synthesis method Methods 0.000 title abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000010189 synthetic method Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical class C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000007524 organic acids Chemical class 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 150000005323 carbonate salts Chemical class 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 2
- 239000013064 chemical raw material Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 239000003429 antifungal agent Substances 0.000 description 3
- 230000008827 biological function Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- MLZSCKRIEGYCKD-UHFFFAOYSA-N 4-methylquinoline-2-carbonitrile Chemical class C1=CC=C2C(C)=CC(C#N)=NC2=C1 MLZSCKRIEGYCKD-UHFFFAOYSA-N 0.000 description 1
- KUQKKIBQVSFDHX-UHFFFAOYSA-N 8-hydroxyquinoline-2-carbonitrile Chemical class C1=C(C#N)N=C2C(O)=CC=CC2=C1 KUQKKIBQVSFDHX-UHFFFAOYSA-N 0.000 description 1
- 241000228232 Aspergillus tubingensis Species 0.000 description 1
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001460074 Microsporum distortum Species 0.000 description 1
- 239000005985 Paclobutrazol Substances 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000006273 synthetic pesticide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a substituted triazole compound and a synthesis method thereof. The substituted triazole compound has the following structural general formula, wherein R1，R2，R3Hydrogen, methyl, ethyl, propyl, chlorine, bromine and hydroxyl. The synthetic method is that substituted 2-cyano quinoline reacts with anhydrous hydrazine, and then the compound reacts under the condition of organic acid to obtain the compound. The reaction method is simple and convenient, the condition is mild, and the yield is high. The substituted triazole compound is an important chemical raw material, and can be applied to the fields of organic synthesis, pesticides, medicines and the like.
Description
Technical field
The present invention relates to a kind of compound and synthetic method thereof, relate in particular to a kind of substituted trinitrogen azole compound and synthetic method thereof.
Background technology
The infection that is caused by pathogenic fungus is a kind of common multiple disease, it is divided into superficial tissues and two kinds of infection of deep tissue, the former is many to be caused by dermatophytosiss such as trichophytons, the latter is usually by cryptococcus, aspergillus tubigensis etc. cause, along with broad-spectrum antibiotics, cortin, being extensive use of of antitumor drug and immunosuppressor and increasing of major surgery, destroyed the symbiotic relationship of normal flora, human body is reduced the resistibility of fungi, thereby cause deep fungal infection to be on the rise, become aids patient, one of leukemia people's main causes of death, as M.M.Canuto, et al, Lancet Infectious Diseases, 2002,2 (9), 550-563 is disclosed.The antifungal drug of early stage development is mainly used in local superficial fungal infection, curative effect to deep infection is still undesirable, in the existing antifungal drug, the triazole class medicine is comparatively desirable to the curative effect of deep fungal infection, and because it has anti-microbial activity height, characteristics such as pharmacokinetics that toxic side effect is little and superior, so be the focus in the antifungal drug research always, as Y.Koltin, et al, Current Opinion in Chemical Biology, 1997,1 (2), what 176-182 explained.
Triazole compound is owing to have effects such as desinsection, weeding, promotion and adjusting crop growth, or the important intermediate of synthetic pesticide sterilant, weedicide, plant-growth regulator such as paclobutrazol, alkene azoles alcohol, triazolone, triadimefon etc., as E.Rodriguez-Fernandez, et al, Journal of InorganicBiochemistry, 2005,99 (8), 1558-1572 is disclosed.Therefore, triazole compound is widely used in fields such as medicine, agricultural chemicals, fine chemistry industry and organic synthesis, is the important fine chemical product of a class.Owing to its special structure, triazole compound also is usually used in synthetic monokaryon and multinuclear function title complex in addition.Existing triazole compound only contains alkyl, phenyl or pyridyl, and the biological function of these groups is relatively poor.
Summary of the invention
The objective of the invention is provides a kind of quinoline substituted trinitrogen azole compound in order to improve existing triazole compound only to contain the deficiency of alkyl, phenyl or pyridyl, another object of the present invention provides the synthetic method of above-mentioned quinoline substituted trinitrogen azole compound, and this method is easy, efficient, mild condition.
Technical scheme of the present invention is: the present invention is with a kind of important alkaloid--the grafting of-quinoline group is to the triazole ring, because of the quinoline group also has bigger conjugated system, the new triazole compound that is obtained will have important biological function and different reactive behavioies.
Concrete technical scheme of the present invention is: the invention provides a kind of substituted trinitrogen azole compound, it is characterized in that its general structure is:
R wherein
1Be hydrogen, methyl, ethyl, propyl group, chlorine, bromine or hydroxyl; R
2Be hydrogen, methyl, ethyl, propyl group, chlorine, bromine or hydroxyl; R
3Be hydrogen, methyl, ethyl, propyl group, chlorine, bromine or hydroxyl.
The present invention also provides the synthetic method of above-claimed cpd, and its concrete steps are:
A. the 2-cyano-quinoline derivatives is dissolved in organic solvent;
B. anhydrous hydrazine is added in the above-mentioned solution and stir, controlled temperature reacts, and after reaction finishes, filters washing, recrystallization;
C. the reaction product of step B gained is added in the organic acid and reacts; Reaction after finishing boils off organic acid, and adding unsaturated carbonate salts solution is neutralized to pH=7～7.5, filtration washing, vacuum-drying;
D. be eluent with methylene dichloride and methyl alcohol, silica gel column chromatography separate pure product.Reaction process as shown in the formula:
The structural formula of wherein said 2-cyano-quinoline derivatives is:
R wherein
1, R
2, R
3Be respectively hydrogen, methyl, ethyl, propyl group, chlorine, bromine or hydroxyl.
The mol ratio of the add-on of anhydrous hydrazine and 2-cyano-quinoline derivatives is (2～15) among the above-mentioned steps B: 1, and temperature of reaction is 20～40 ℃, the reaction times is 0.5～10 hour.
Organic acid described in the step C is acetate, formic acid or propionic acid, and the mol ratio of organic acid add-on and raw material 2-cyano-quinoline derivatives is (5～10): 1, and the reaction times is 3～24 hours.
Organic solvent in the steps A is a polar solvent, preferably uses the solvent of drying, particular methanol, ethanol or acetonitrile; Unsaturated carbonate salts solution among the step C is sodium hydrogen carbonate solution, potassium bicarbonate solution or sodium carbonate solution.
Because the substituted triazole compounds is widely used in fields such as medicine, agricultural chemicals, organic synthesis, it is the important fine chemical product of a class, in many molecules with physiologically active, also comprise the triazole species structural unit, so utilize institute of the present invention synthetic substituted triazole compounds to be expected to be converted into important pharmaceutical intermediate.
Beneficial effect:
1, the present invention finds a kind of new substituted trinitrogen azole compound, and this compounds is because of containing quinoline group (a kind of important alkaloid and bigger conjugated system), so have important biological function and different reactive behavioies.
2, simple to operate, the mild condition of synthetic method of the present invention, productive rate height generally reach 73～83%.
Embodiment
The invention will be further described below by example, but do not limit protection scope of the present invention.
Embodiment one:
With 2-cyano quinolines (2.156g, 14mmol) be dissolved in the dehydrated alcohol, add again anhydrous hydrazine (8.75mL, 150mmol), 30 ℃ are stirred 2h down, after filtration, washing, the drying, 0 ℃ add acetate (7.86g, 131mmol), heating reflux reaction 3h then, be cooled to room temperature, pressure reducing and steaming acetate adds saturated NaHCO
3Solution is regulated pH=7, filters washing, and drying is an eluent with methylene dichloride and methyl alcohol, and silica gel column chromatography gets pure product, productive rate 83%.M/Z：324.1(M+1)；323.1(M)。
Embodiment two:
With 8-hydroxyl-2-cyano quinolines (0.850g, 5mmol) be dissolved in the methyl alcohol, add again anhydrous hydrazine (1.17mL, 20mmol), 20 ℃ are stirred 1h down, after filtration, washing, the drying, 0 ℃ add acetate (1.8g, 30mmol), heating reflux reaction 5h then, be cooled to room temperature, pressure reducing and steaming acetate adds saturated KHCO
3Solution is regulated pH=7.5, and filtration, washing, drying are eluent with methylene dichloride and methyl alcohol, and silica gel column chromatography gets pure product, productive rate 73%.M/Z：355.1(M)。
Embodiment three:
With 4-methyl-2-cyano quinolines (2.352g, 14mmol) be dissolved in the acetonitrile, add again anhydrous hydrazine (8.75mL, 150mmol), 25 ℃ are stirred 3h down, after filtration, washing, the drying, 0 ℃ add acetate (7.56g, 126mmol), heating reflux reaction 6h then, be cooled to room temperature, pressure reducing and steaming acetate adds saturated Na
2CO
3Solution is regulated pH=7, and filtration, washing, drying are eluent with methylene dichloride and methyl alcohol, and silica gel column chromatography gets pure product, productive rate 80%.M/Z：351.1(M)。
Claims (6)
1. substituted trinitrogen azole compound is characterized in that its general structure is:
R wherein
1, R
2, R
3Be respectively hydrogen, methyl, ethyl, propyl group, chlorine, bromine or hydroxyl.
2. synthetic method of compound according to claim 1, its concrete steps are:
A. the 2-cyano-quinoline derivatives is dissolved in organic solvent;
B. anhydrous hydrazine is added in the above-mentioned solution and stir, controlled temperature reacts, and after reaction finishes, filters washing, recrystallization;
C. the reaction product of step B gained is added in the organic acid and reacts; Reaction after finishing boils off organic acid, and adding unsaturated carbonate salts solution is neutralized to pH=7～7.5, filtration washing, vacuum-drying;
D. be eluent with methylene dichloride and methyl alcohol, silica gel column chromatography separate pure product.
3. synthetic method according to claim 2 is characterized in that the structural formula of 2-cyano-quinoline derivatives is:
R wherein
1, R
2, R
3Be respectively hydrogen, methyl, ethyl, propyl group, chlorine, bromine or hydroxyl.
4. synthetic method according to claim 2 is characterized in that the add-on of anhydrous hydrazine among the step B and the mol ratio of 2-cyano-quinoline derivatives are (2～15): 1, and temperature of reaction is 20～40 ℃, the reaction times is 0.5～10 hour.
5. synthetic method according to claim 2 is characterized in that the organic acid described in the step C is acetate, formic acid or propionic acid, and the mol ratio of organic acid add-on and raw material 2-cyano-quinoline derivatives is (5～10): 1, and the reaction times is 3～24 hours.
6. synthetic method according to claim 2 is characterized in that the organic solvent in the steps A is methyl alcohol, ethanol or acetonitrile; Unsaturated carbonate salts solution among the step C is sodium hydrogen carbonate solution, potassium bicarbonate solution or sodium carbonate solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101334550A CN101139342A (en) | 2007-09-30 | 2007-09-30 | Substituted triazole compound and synthesis method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101334550A CN101139342A (en) | 2007-09-30 | 2007-09-30 | Substituted triazole compound and synthesis method thereof |
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| Publication Number | Publication Date |
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| CN101139342A true CN101139342A (en) | 2008-03-12 |
Family
ID=39191467
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| Application Number | Title | Priority Date | Filing Date |
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| CNA2007101334550A Pending CN101139342A (en) | 2007-09-30 | 2007-09-30 | Substituted triazole compound and synthesis method thereof |
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104230828A (en) * | 2014-08-25 | 2014-12-24 | 浙江大学 | Method for synthesizing 1,4-disubstituted triazole compounds by one-pot process |
-
2007
- 2007-09-30 CN CNA2007101334550A patent/CN101139342A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104230828A (en) * | 2014-08-25 | 2014-12-24 | 浙江大学 | Method for synthesizing 1,4-disubstituted triazole compounds by one-pot process |
| CN104230828B (en) * | 2014-08-25 | 2016-08-24 | 浙江大学 | The method of one pot process 1,4-bis-substituted triazole compound |
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Open date: 20080312 |