CN1948287A - Acetyl-2,6-dimethyl pyridine-3,5-diethyl ketone hydrazone and its synthesis method - Google Patents
Acetyl-2,6-dimethyl pyridine-3,5-diethyl ketone hydrazone and its synthesis method Download PDFInfo
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- CN1948287A CN1948287A CN 200610118164 CN200610118164A CN1948287A CN 1948287 A CN1948287 A CN 1948287A CN 200610118164 CN200610118164 CN 200610118164 CN 200610118164 A CN200610118164 A CN 200610118164A CN 1948287 A CN1948287 A CN 1948287A
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- Prior art keywords
- acetyl
- diethyl ketone
- pyridine
- dimethyl
- ketone hydrazone
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Abstract
The present invention relates to a kind of acetyl-2,6-dimethyl-pyridine-3,5-diethylketohydrazone and its synthesis method. Said invention also provides its chemical structure formula, and its synthesis method includes the following steps: using ethyl alcohol as system, using glacial acetic acid as catalyst, making refluxing reaction for 3-4 h, the mole ratio of reactant 2,6-dimethyl 3,5-diacetylpyridine and acethydrazide is 1:2.0-3.0, after the reaction is completed, standing still, cooling and separating out solid, simple treatment so as to obtain the invented acetyl-2,6-dimethyl-pyridine-3,5-diethylketohydrazone.
Description
Technical field
The present invention relates to a kind of hydrazone and synthetic method thereof, particularly acetyl-2 that contains pyridine ring, 6-lutidine-3,5-diethyl ketone hydrazone.
Background technology
Pyridine is common but crucial heterogeneous ring compound in the organic synthesis, of many usesly can reduce 4 aspects, i.e. medicine and intermediate, agricultural chemicals and intermediate, chemical intermediate, dyestuff.For example medicine and intermediate have Norxin, vitamin A, antitumor drug dexamethasone, acetylspiramycin, nicotinic acid, niacinamide, Yi Yansuan, bromination pentadecyl pyridine, 2-vinyl pyridine; Chemical industry and intermediate have oxo pyridine, Perchloropyridine; Dyestuff has N-ethylpyridine ketone series.Particularly Application Areass all in the agricultural chemicals and various structure type have been spreaded all over as agricultural chemicals and intermediate pyridine thereof, particularly the pyridines sterilant--after nicotine nitro alkene class was developed, the patent that contains the pyridines novel pesticide increased sharply, is worth coming into the picture.See from structure type that from structure type except that individually comparatively the uniqueness, the overwhelming majority has formed series.To sulfonylurea, imidazolone type agricultural chemicals the compound that contains pyridine is arranged all from organophosphorus, amino formate.Wherein the organic phosphates agricultural chemicals that contains pyridine has
The carbamate chemicals for agriculture that contains pyridine has
The agricultural chemicals that contains the pyridine pyrethroid has
The acylhydrazone compounds is owing to contain a class good active substructure group (CONHN=CH-) in the molecular structure, thereby show biological activitys such as good weeding and sterilization, be one of focus of present agricultural chemicals circle research " simultaneously; ligating atoms such as oxygen that hydrazone compound provides and nitrogen; can form the special acylhydrazone title complex of structures; this class title complex not only has the pharmacologically active of unique tuberculosis germ and anti-inflammatory, sterilization and physiologically active such as antitumor, and its double-core zinc alkali type title complex can also be as the model compound of research native metal enzyme with many metals.
Summary of the invention
One of purpose of the present invention is to provide a kind of acylhydrazone compounds acetyl-2,6-lutidine-3,5-diethyl ketone hydrazone.
It is a kind of with 2 that two of purpose of the present invention is to provide, and 6-dimethyl-3,5-diacetyl pyridine are starting raw material, the method for synthetic this compound.
For achieving the above object, the reaction mechanism that the inventive method has adopted is:
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of acetyl-2,6-lutidine-3, the 5-diethyl ketone hydrazone is characterized in that, the structure of this compound is:
The physical parameter of this compound:
Molecular formula: C
15H
21N
5O
2
Structural formula:
Chinese named: acetyl 2,6-lutidine-3,5-diethyl ketone hydrazone
English name: Acetyl-2.6-dimethyl-pyridyl-3,5-diacetyl hydrazone
Molecular weight: 303.4
Outward appearance: white solid
Fusing point (adopting WRS-1B numeral fusing point instrument): 200.3-201.3 ℃
Mass spectrum (adopt the HP5898-A mass spectrograph, EI, 70ev):
m/e：303(M
++1，9.7)，302(M
+，11.2)，288(68.1)，245(98.7)，204(100)，43(62.0)。
Proton nmr spectra (500MHz, CDCl
3, interior mark: TMS):
10.45～10.37 (2H, NH), 7.64～7.58 (1H, pyridine ring H), 2.51 (6H, CH3), 2.22～2.21 (6H, CH3), 2.026 (6H, CH3).
Infrared spectra (adopting the Perkin-Elmer983G infrared spectrometer, the KBr compressing tablet):
υmax(cm
-1)：3194，1675，1605，1536，1431，1394。
Above-mentioned acetyl-2,6-lutidine-3, the synthetic method of 5-diethyl ketone hydrazone, it is characterized in that this method has following steps: as system, the Glacial acetic acid that adds catalyst levels is as catalyzer with ethanol, back flow reaction 3～4 hours, reactant 2,6-dimethyl-3, the mol ratio of 5-diacetyl pyridine and acethydrazide is 1: 2.0-3.0; Reaction is left standstill cooling after finishing, through suction filtration, and washing, drying obtains acetyl-2,6-lutidine-3,5-diethyl ketone hydrazone white powder solid.
That the present invention has is simple to operate, mild condition, productive rate advantages of higher.
Embodiment:
In the there-necked flask that example is: 25 milliliter, add 1.01 grams 2,6-dimethyl-3,5-diacetyl pyridine, 0.8 gram acethydrazide, 5 Glacial acetic acid, 10 milliliters of ethanol, reflux 3 hours.Cooling, suction filtration washes twice with water, gets acetyl-2,6-lutidine-3,5-diethyl ketone hydrazone 0.9 gram, productive rate 56.2%.
In the there-necked flask that example is two: 250 milliliters, add 10.3 gram 2,6 dimethyl-3,5-diacetyl pyridine, 9.6 gram acethydrazides, 2 milliliters of Glacial acetic acid, 100 milliliters of ethanol, reflux 3 hours.Cooling, suction filtration washes twice with water, gets acetyl-2 after the drying, 6-lutidine-3,5-diethyl ketone hydrazone 9.1 grams, productive rate 56.8%.
In the there-necked flask that example is three: 2 liters, add 100 grams 2,6-dimethyl-3,5-diacetyl pyridine, 110 gram acethydrazides, 5 milliliters of Glacial acetic acid, 1000 milliliters of ethanol, reflux 3 hours.Cooling, suction filtration washes twice with water, gets acetyl-2 after the drying, 6-lutidine-3,5-diethyl ketone hydrazone 87.6 grams, productive rate 55.2%.
Claims (2)
1. acetyl-2,6-lutidine-3, the 5-diethyl ketone hydrazone is characterized in that, the structure of this compound is:
2. one kind is synthesized acetyl according to claim 1-2,6-lutidine-3, the method of 5-diethyl ketone hydrazone, it is characterized in that this method has following steps: with ethanol as system, the Glacial acetic acid that adds catalyst levels is as catalyzer, back flow reaction 3～4 hours, reactant 2,6-dimethyl-3, the mol ratio of 5-diacetyl pyridine and acethydrazide are 1: 2.0-3.0; Reaction is left standstill cooling after finishing, through suction filtration, and washing, drying obtains acetyl-2,6-lutidine-3,5-diethyl ketone hydrazone white powder solid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610118164 CN1948287A (en) | 2006-11-09 | 2006-11-09 | Acetyl-2,6-dimethyl pyridine-3,5-diethyl ketone hydrazone and its synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610118164 CN1948287A (en) | 2006-11-09 | 2006-11-09 | Acetyl-2,6-dimethyl pyridine-3,5-diethyl ketone hydrazone and its synthesis method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1948287A true CN1948287A (en) | 2007-04-18 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200610118164 Pending CN1948287A (en) | 2006-11-09 | 2006-11-09 | Acetyl-2,6-dimethyl pyridine-3,5-diethyl ketone hydrazone and its synthesis method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101787018A (en) * | 2010-03-17 | 2010-07-28 | 上海大学 | 2,6-dimethyl 3,5-bis-[4,4'-(2-amino-3-cyano-thiophene)] pyridine and synthetic method thereof |
| CN102276593A (en) * | 2011-07-01 | 2011-12-14 | 华东师范大学 | Heterocyclic ketene hydrazone compound and preparation method as well as tubercle bacillus resistant application |
| CN105669708A (en) * | 2016-01-18 | 2016-06-15 | 新乡医学院 | Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof |
-
2006
- 2006-11-09 CN CN 200610118164 patent/CN1948287A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101787018A (en) * | 2010-03-17 | 2010-07-28 | 上海大学 | 2,6-dimethyl 3,5-bis-[4,4'-(2-amino-3-cyano-thiophene)] pyridine and synthetic method thereof |
| CN102276593A (en) * | 2011-07-01 | 2011-12-14 | 华东师范大学 | Heterocyclic ketene hydrazone compound and preparation method as well as tubercle bacillus resistant application |
| CN102276593B (en) * | 2011-07-01 | 2013-10-30 | 华东师范大学 | Heterocyclic ketene hydrazone compound and preparation method as well as tubercle bacillus resistant application |
| CN105669708A (en) * | 2016-01-18 | 2016-06-15 | 新乡医学院 | Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof |
| CN105669708B (en) * | 2016-01-18 | 2019-06-21 | 新乡医学院 | One kind is based on cumarin schiff bases copper ion complex mercaptan fluorescence probe and its preparation method and application |
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