CN105367543B - A kind of thiophene chalcone semicarbazones Schiff class compound and preparation method thereof, application - Google Patents
A kind of thiophene chalcone semicarbazones Schiff class compound and preparation method thereof, application Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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Abstract
The present invention provides a kind of thiophene chalcone semicarbazones Schiff class compound and preparation method thereof, application, wherein the general structure of the compound is as follows:
Description
Technical field
The present invention relates to technical field of pesticide more particularly to a kind of thiophene chalcone semicarbazones Schiff class compounds
And preparation method thereof, application.
Background technique
Schiff refer to condensation reaction occurs by primary amine and aldehydes or ketones and generate contain > one kind of C=N- structure has
Machine compound.A large number of studies show that Schiff class compound is in medicine, catalysis, analytical chemistry, corrosion and photochromic etc.
Field suffers from very important effect.Meanwhile Schiff class compound also has good bioactivity, for example, desinsection,
Antimycotic, antibacterium, anticancer, anti parasitic, weeding etc..Therefore, the research and development of Schiff class compound will have
Wide space.
Thiophene is a member important in heterocyclic compound, plays very important effect.The research of thiophene derivant is being cured
Also there is very main effect in medicine and chemistry of pesticide.Thiophene derivant has various bioactivity, for example, suppression
Bacterium, antiviral and antitumor, anti-inflammatory, desinsection and weeding etc..Meanwhile the compound containing thiphene ring usually all have efficiently, low toxicity,
To non-target organism safety, easy degradation, harmful organism do not allow the features such as being also easy to produce resistance, and constantly have structure in the environment
Compound that is novel, haveing excellent performance comes out.So during the research and development of pesticide, the compound containing thiphene ring will be by
To more extensive concern, become hot spot and the forward position of New pesticides discovery.
Up to the present, yet there are no thiophene chalcone semicarbazones Schiff class compound makes as disinfectant use in agriculture
Report.
Summary of the invention
Thiphene ring is introduced into the molecular structure of Schiff by the present invention, has synthesized some thiophene chalcone semicarbazones
Schiff derivative, it was found that the reactive compound or active lead compound of some structure novels, superior activity, are new agriculture
Preferable basis has been established in the initiative of medicine.
A kind of thiophene chalcone semicarbazones Schiff class compound, general structure are as follows:
R is fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group or phenyl in logical formula (I), R be one replace or
Two replace.
A kind of preparation method of thiophene chalcone semicarbazones Schiff class compound, comprising: the synthesis of intermediate and
Using the intermediate come two steps of synthesising target compound.
Further, method as described above, the synthesis of the intermediate the following steps are included:
A, NaOH solution is added into the mixture of acetophenone derivs and dehydrated alcohol, forms solution I；
B, under ice bath stirring, the mixed liquor of 2 thiophene carboxaldehyde and dehydrated alcohol is slowly instilled in the solution I and is carried out
Reaction forms solution II；
C, after the completion of answering, distilled water is added to solution II, adjusts its pH value to neutrality, there is Precipitation, filters, washing,
It is recrystallized with dehydrated alcohol again to get intermediate is arrived.
Further, method as described above, the acetophenone derivs be 3,4- dichloroacetophenone, 3- bromoacetophenone,
One of 3- chloro-acetophenone, biphenyl list ethyl ketone, 4- fluoro acetophenone.
Further, method as described above, in the step b, reaction temperature is 0-5 DEG C.
Further, method as described above, the synthesis of target compound the following steps are included:
E, glacial acetic acid is added into the mixture of semicarbazides and ethyl alcohol, forms mixed solution I II；
F, under agitation, the mixed solution of the intermediate and dehydrated alcohol is slowly instilled to above-mentioned mixed solution
It is reacted in III；
G, its pH value after the reaction was completed, is adjusted to neutrality with NaOH, is had Precipitation, is filtered, again with anhydrous second after washing
Alcohol recrystallization, finally obtains target compound of the present invention.
Further, method as described above, in the step f, the condition of reaction are as follows: reacted at 70 DEG C 20 hours with
On.
A kind of thiophene chalcone semicarbazones Schiff class compound as described above is for preventing and treating plant pathogenic fungi
Purposes.
Further, purposes as described above, the plant pathogenic fungi be Rhizoctonia solani Kuhn, fusarium graminearum,
Southern corn leaf blight, Sclerotinia sclerotiorum, botrytis cinerea, fruit white rot of grape bacterium, Colletotrichumlagenarium, ring rot of apple
Bacterium, citrus common green mold bacterium and phytophthora infestans.
Compound structure provided by the invention is simple, novel, is readily synthesized, and has preferable prevention and treatment effect to plant pathogenic fungi
Fruit.It is had not been reported in the plant pathogenic fungi inhibitor being currently known.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, the technical solution below in the present invention carries out clear
Chu is fully described by, it is clear that described embodiments are some of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
The present invention provides a kind of compound with bacteriostatic activity, general structure is as follows:
R is fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group or phenyl in logical formula (I), and R can take for one
Generation or two substitutions.
General formula is the key reaction equation in the preparation of compounds of (I) are as follows:
The meaning of R is same as above in formula.
Embodiment 1:
Compound(C14H12ON3SF preparation)
(1) synthesis of intermediate 1- (4- fluorophenyl) -3- (2- thienyl) -2- propylene -1- ketone
0.02mol 4- fluoro acetophenone is dissolved in 30mL dehydrated alcohol, then addition 10mL 10%NaOH is molten thereto
Liquid.Under ice bath stirring, slowly with constant pressure funnel by the mixed liquor of 0.02mol 2 thiophene carboxaldehyde and 20mL dehydrated alcohol
It instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction is completed
Afterwards, the distilled water of 3-4 times of volume is added into mixture, and adjusts its pH value to neutrality with 10% HCl, there is Precipitation,
Filtering, washing, then recrystallized with dehydrated alcohol to get intermediate 1- (4- fluorophenyl) -3- (2- thienyl) -2- propylene -1- is arrived
Ketone.
(2) synthesis of target compound
0.015mol semicarbazides is dissolved in 90% ethyl alcohol of 20mL, 1.5mL glacial acetic acid is added thereto.In stirring bar
Under part, the mixed solution of the homemade intermediate of 0.015mol and 30mL dehydrated alcohol is slowly instilled with constant pressure funnel above-mentioned
It in mixed solution, is reacted 20 hours or more at 70 DEG C, and checks whether reaction is completed with TLC.After the reaction was completed, with 10%
NaOH adjusts its pH value to neutrality, has Precipitation, filters, recrystallized again with dehydrated alcohol after washing, obtain pale yellow powder
Shape solid product, yield 82%.The spectral data of product is as follows:
1H NMR(300MHz,DMSO-d6) δ (ppm): 10.17 (s, 1H), 7.61 (t, J=4.5Hz, 2H), 7.57 (d, J
=5.7Hz, 1H), 7.36 (s, 1H), 7.33 (d, J=13.5Hz, 1H), 7.25 (t, J=9.0Hz, 2H), 7.09-7.07 (m,
1H), 6.85 (d, J=15.9Hz, 1H), 6.42 (s, 2H)；13C NMR(75MHz,DMSO-d6)δ(ppm):164.27-161.01
(d,1C),157.60(1C),145.00(1C),141.40(1C),134.14-134.10(d,1C),131.43-131.32(d,
2C),131.36(1C),129.80(1C),128.49(1C),128.42(1C),117.70(1C),115.61-115.32(d,
2C)。
Embodiment 2:
Compound(C20H17ON3S preparation)
(1) synthesis of intermediate 1- (4- xenyl) -3- (2- thienyl) -2- propylene -1- ketone
0.02mol biphenyl list ethyl ketone is dissolved in 30mL dehydrated alcohol, then addition 10mL 10%NaOH is molten thereto
Liquid.Under ice bath stirring, slowly with constant pressure funnel by the mixed liquor of 0.02mol 2 thiophene carboxaldehyde and 20mL dehydrated alcohol
It instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction is completed
Afterwards, the distilled water of 3-4 times of volume is added into mixture, and adjusts its pH value to neutrality with 10% HCl, there is Precipitation,
Filtering, washing, then recrystallized with dehydrated alcohol to get intermediate 1- (4- xenyl) -3- (2- thienyl) -2- propylene -1- is arrived
Ketone.
(2) synthesis of target compound
0.015mol semicarbazides is dissolved in 90% ethyl alcohol of 20mL, 1.5mL glacial acetic acid is added thereto.In stirring bar
Under part, the mixed solution of the homemade intermediate of 0.015mol and 30mL dehydrated alcohol is slowly instilled with constant pressure funnel above-mentioned
It in mixed solution, is reacted 20 hours or more at 70 DEG C, and checks whether reaction is completed with TLC.After the reaction was completed, with 10%
NaOH adjusts its pH value to neutrality, has Precipitation, filters, recrystallized again with dehydrated alcohol after washing, obtain yellow powder
Solid product, yield 80%.The spectral data of product is as follows:
1H NMR(300MHz,DMSO-d6) δ (ppm): 10.18 (s, 1H), 7.73-7.62 (m, 7H), 7.49 (t, J=
7.2Hz, 2H), 7.41-7.33 (m, 3H), 7.09 (t, J=4.8Hz, 1H), 6.95 (d, J=15.9Hz, 1H), 6.43 (s,
2H)；13C NMR(75MHz,DMSO-d6)δ(ppm):157.58(1C),145.59(1C),141.48(1C),140.58(1C),
139.98(1C),136.83(1C),131.38(1C),129.83(2C),129.75(1C),129.39(2C),128.43(2C),
128.01(1C),127.01(2C),126.88(2C),117.74(1C)。
Embodiment 3:
Compound(C14H12ON3SCl preparation)
(1) synthesis of intermediate 1- (3- chlorphenyl) -3- (2- thienyl) -2- propylene -1- ketone
0.02mol 3- chloro-acetophenone is dissolved in 30mL dehydrated alcohol, then addition 10mL 10%NaOH is molten thereto
Liquid.Under ice bath stirring, slowly with constant pressure funnel by the mixed liquor of 0.02mol 2 thiophene carboxaldehyde and 20mL dehydrated alcohol
It instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction is completed
Afterwards, the distilled water of 3-4 times of volume is added into mixture, and adjusts its pH value to neutrality with 10% HCl, there is Precipitation,
Filtering, washing, then recrystallized with dehydrated alcohol to get intermediate 1- (3- chlorphenyl) -3- (2- thienyl) -2- propylene -1- is arrived
Ketone.
(2) synthesis of target compound
0.015mol semicarbazides is dissolved in 90% ethyl alcohol of 20mL, 1.5mL glacial acetic acid is added thereto.In stirring bar
Under part, the mixed solution of the homemade intermediate of 0.015mol and 30mL dehydrated alcohol is slowly instilled with constant pressure funnel above-mentioned
It in mixed solution, is reacted 20 hours or more at 70 DEG C, and checks whether reaction is completed with TLC.After the reaction was completed, with 10%
NaOH adjusts its pH value to neutrality, has Precipitation, filters, recrystallized again with dehydrated alcohol after washing, obtain pale yellow powder
Shape solid product, yield 81%.The spectral data of product is as follows:
1H NMR(300MHz,DMSO-d6)δ(ppm):10.19(s,1H),7.63–7.61(m,2H),7.51–7.41(m,
3H), 7.37 (d, J=3.3Hz, 1H), 7.32 (d, J=16.2Hz, 1H), 7.09 (t, J=3.9Hz, 1H), 6.86 (d, J=
15.9Hz,1H),6.46(s,2H)；13C NMR(75MHz,DMSO-d6)δ(ppm):157.44(1C),144.38(1C),
141.34(1C),139.85(1C),133.51(1C),131.35(1C),130.38(1C),129.88(1C),128.82(1C),
128.74(1C),128.55(1C),128.42(1C),127.97(1C),117.43(1C)。
Embodiment 4:
Compound(C14H12ON3SBr preparation)
(1) synthesis of intermediate 1- (3- bromophenyl) -3- (2- thienyl) -2- propylene -1- ketone
0.02mol 3- bromoacetophenone is dissolved in 30mL dehydrated alcohol, then addition 10mL 10%NaOH is molten thereto
Liquid.Under ice bath stirring, slowly with constant pressure funnel by the mixed liquor of 0.02mol 2 thiophene carboxaldehyde and 20mL dehydrated alcohol
It instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction is completed
Afterwards, the distilled water of 3-4 times of volume is added into mixture, and adjusts its pH value to neutrality with 10% HCl, there is Precipitation,
Filtering, washing, then recrystallized with dehydrated alcohol to get intermediate 1- (3- bromophenyl) -3- (2- thienyl) -2- propylene -1- is arrived
Ketone.
(2) synthesis of target compound
0.015mol semicarbazides is dissolved in 90% ethyl alcohol of 20mL, 1.5mL glacial acetic acid is added thereto.In stirring bar
Under part, the mixed solution of the homemade intermediate of 0.015mol and 30mL dehydrated alcohol is slowly instilled with constant pressure funnel above-mentioned
It in mixed solution, is reacted 20 hours or more at 70 DEG C, and checks whether reaction is completed with TLC.After the reaction was completed, with 10%
NaOH adjusts its pH value to neutrality, has Precipitation, filters, recrystallized again with dehydrated alcohol after washing, obtain light yellow crystal
Product, yield 83%.The spectral data of product is as follows:
1H NMR(300MHz,DMSO-d6)δ(ppm):10.21(s,1H),7.73(s,1H),7.61(s,1H),7.59(s,
1H), 7.53 (d, J=7.5Hz, 1H), 7.40 (s, 1H), 7.35 (s, 1H), 7.30 (s, 1H), 7.08 (s, 1H), 6.86 (d, J
=15.9Hz, 1H), 6.47 (s, 2H)；13C NMR(75MHz,DMSO-d6)δ(ppm):157.44(1C),144.34(1C),
141.33(1C),140.09(1C),131.64(2C),131.35(1C),130.66(1C),129.90(1C),128.57(1C),
128.43(1C),128.37(1C),122.09(1C),117.45(1C)。
Embodiment 5:
Compound(C14H11ON3SCl2) preparation
(1) synthesis of intermediate 1- (3,4- dichlorophenyl) -3- (2- thienyl) -2- propylene -1- ketone
By 0.02mol 3,4- dichloroacetophenone is dissolved in 30mL dehydrated alcohol, then 10mL 10% is added thereto
NaOH solution.Under ice bath stirring, the mixed liquor of 0.02mol 2 thiophene carboxaldehyde and 20mL dehydrated alcohol is leaked with constant pressure addition
Bucket slowly instills in above-mentioned mixed solution, reacts at 0-5 DEG C, and checks whether reaction is completed with thin layer silica gel plate (TLC).Instead
After the completion of answering, the distilled water of 3-4 times of volume is added into mixture, and adjusts its pH value to neutrality with 10% HCl, there is precipitating
It is precipitated, filters, washing, then recrystallized with dehydrated alcohol to get intermediate 1- (3,4- dichlorophenyl) -3- (2- thienyl)-is arrived
2- propylene -1- ketone.
(2) synthesis of target compound
0.015mol semicarbazides is dissolved in 90% ethyl alcohol of 20mL, 1.5mL glacial acetic acid is added thereto.In stirring bar
Under part, the mixed solution of the homemade intermediate of 0.015mol and 30mL dehydrated alcohol is slowly instilled with constant pressure funnel above-mentioned
It in mixed solution, is reacted 20 hours or more at 70 DEG C, and checks whether reaction is completed with TLC.After the reaction was completed, with 10%
NaOH adjusts its pH value to neutrality, has Precipitation, filters, recrystallized again with dehydrated alcohol after washing, obtain pale yellow powder
Shape solid product, yield 84%.The spectral data of product is as follows:
1H NMR(300MHz,DMSO-d6) δ (ppm): 10.23 (s, 1H), 7.82 (d, J=2.1Hz, 1H), 7.66 (d, J
=8.4Hz, 1H), 7.62 (d, J=5.1Hz, 1H), 7.52 (dd, J1=2.1Hz, J2=2.1Hz, 1H), 7.37 (d, J=
3.6Hz, 1H), 7.31 (d, J=15.9Hz, 1H), 7.10-7.07 (m, 1H), 6.91 (d, J=15.9Hz, 1H), 6.51 (s,
2H)；13C NMR(75MHz,DMSO-d6)δ(ppm):157.45(1C),143.40(1C),141.32(1C),138.35(1C),
131.58(1C),131.47(2C),130.90(1C),130.64(1C),129.95(1C),129.43(1C),128.62(1C),
128.40(1C),117.16(1C)。
Experimental example:
Antibacterial Activity of the thiophene chalcone semicarbazones Schiff class compound to plant pathogenic fungi
1, test plant disease fungus
Rhizoctonia solani Kuhn, fusarium graminearum, southern corn leaf blight, Sclerotinia sclerotiorum, botrytis cinerea, grape
White rot germ, Colletotrichumlagenarium, Botryosphaeria berengeriana f. sp, citrus common green mold bacterium and phytophthora infestans.
2, experimental method
Test compound is dissolved in dimethyl sulfoxide, is then added in the tap water containing 0.1% Tween-80, mixing is equal
The test solution of 200mg/L is made into after even.This solution is added in sterilized PDA culture medium, while adding concentration and being
The streptomysin of 50mg/L.Using the corresponding solution without test compound as blank control, it is standby that the uniform drug containing tablet of thickness is made
With in triplicate.Ф 5mm well-grown, pollution-free, the uniform bacteria cake of growing way are chosen with sterilized punch, in sterile item
The center (one bacteria cake of each plating) that toxic culture medium and control medium are accessed under part, is trained under 28 DEG C of constant temperatures
It supports.When the colony diameter of blank control grows to 50mm or so, using the diameter of crossing method measurement bacterium colony, take it average
Value calculates opposite bacteriostasis rate with following equation:
3, experimental result
Thiophene chalcone semicarbazones Schiff class compound to the Antibacterial Activity result of plant pathogenic fungi such as
Shown in table 1-5.
1 embodiment of table, 1 compound is in 200mg/L to the inhibitory activity of plant pathogenic fungi
| Strain | Inhibiting rate (%) | Strain | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 86.7 | Fusarium graminearum | 93.1 |
| Southern corn leaf blight | 95.3 | Sclerotinia sclerotiorum | 77.9 |
| Botrytis cinerea | 73.2 | Fruit white rot of grape bacterium | 72.8 |
| Colletotrichumlagenarium | 76.5 | Botryosphaeria berengeriana f. sp | 82.4 |
| Citrus common green mold bacterium | 81.9 | Phytophthora infestans | 64.2 |
As known from Table 1,1 compound of embodiment has good inhibitory effect to fusarium graminearum and southern corn leaf blight；
There is preferable inhibitory effect to Rhizoctonia solani Kuhn, Botryosphaeria berengeriana f. sp and citrus common green mold bacterium.
2 embodiment of table, 2 compound is in 200mg/L to the inhibitory activity of plant pathogenic fungi
| Strain | Inhibiting rate (%) | Strain | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 62.6 | Fusarium graminearum | 97.4 |
| Southern corn leaf blight | 95.8 | Sclerotinia sclerotiorum | 76.8 |
| Botrytis cinerea | 92.3 | Fruit white rot of grape bacterium | 70.2 |
| Colletotrichumlagenarium | 61.9 | Botryosphaeria berengeriana f. sp | 84.1 |
| Citrus common green mold bacterium | 83.5 | Phytophthora infestans | 85.7 |
As known from Table 2,2 compound of embodiment has very fusarium graminearum, southern corn leaf blight and botrytis cinerea
Good inhibitory effect；There is preferable inhibitory effect to Botryosphaeria berengeriana f. sp, citrus common green mold bacterium and phytophthora infestans.
3 embodiment of table, 3 compound is in 200mg/L to the inhibitory activity of plant pathogenic fungi
| Strain | Inhibiting rate (%) | Strain | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 65.6 | Fusarium graminearum | 92.4 |
| Southern corn leaf blight | 61.9 | Sclerotinia sclerotiorum | 88.3 |
| Botrytis cinerea | 76.2 | Fruit white rot of grape bacterium | 72.9 |
| Colletotrichumlagenarium | 68.7 | Botryosphaeria berengeriana f. sp | 84.6 |
| Citrus common green mold bacterium | 83.7 | Phytophthora infestans | 74.5 |
As known from Table 3,3 compound of embodiment has good inhibitory effect to fusarium graminearum；To Sclerotinia sclerotiorum,
Botryosphaeria berengeriana f. sp and citrus common green mold bacterium have preferable inhibitory effect.
4 embodiment of table, 4 compound is in 200mg/L to the inhibitory activity of plant pathogenic fungi
As known from Table 4,4 compound of embodiment is to fusarium graminearum, southern corn leaf blight, botrytis cinerea and grape
White rot germ has good inhibitory effect；There is preferable inhibitory effect to Sclerotinia sclerotiorum and citrus common green mold bacterium.
5 embodiment of table, 5 compound is in 200mg/L to the inhibitory activity of plant pathogenic fungi
| Strain | Inhibiting rate (%) | Strain | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 68.5 | Fusarium graminearum | 83.2 |
| Southern corn leaf blight | 65.9 | Sclerotinia sclerotiorum | 93.8 |
| Botrytis cinerea | 91.7 | Fruit white rot of grape bacterium | 76.7 |
| Colletotrichumlagenarium | 64.8 | Botryosphaeria berengeriana f. sp | 87.4 |
| Citrus common green mold bacterium | 81.6 | Phytophthora infestans | 86.3 |
As known from Table 5,5 compound of embodiment has good inhibitory effect to Sclerotinia sclerotiorum and botrytis cinerea；
There is preferable inhibitory effect to fusarium graminearum, Botryosphaeria berengeriana f. sp, citrus common green mold bacterium and phytophthora infestans.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although
Present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: it still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features；
And these are modified or replaceed, technical solution of various embodiments of the present invention that it does not separate the essence of the corresponding technical solution spirit and
Range.
Claims (1)
1. a kind of preparation method of thiophene chalcone semicarbazones Schiff class compound characterized by comprising intermediate
Synthesis and using the intermediate come two steps of synthesising target compound；
The synthesis of the intermediate the following steps are included:
A, NaOH solution is added into the mixture of acetophenone derivs and dehydrated alcohol, forms solution I；
B, under ice bath stirring, 2 thiophene carboxaldehyde is slowly instilled in the solution I with the mixed liquor of dehydrated alcohol and is reacted,
Form solution II；
C, after the completion of answering, distilled water is added to solution II, adjusts its pH value to neutrality, has Precipitation, filter, wash, then use
Dehydrated alcohol recrystallizes to arrive intermediate；
The synthesis of target compound the following steps are included:
E, glacial acetic acid is added into the mixture of semicarbazides and ethyl alcohol, forms mixed solution I II；
F, under agitation, the mixed solution of the intermediate and dehydrated alcohol is slowly instilled in above-mentioned mixed solution I II
It is reacted；
G, its pH value after the reaction was completed, is adjusted to neutrality with NaOH, is had Precipitation, is filtered, again with dehydrated alcohol weight after washing
Crystallization, finally obtains target compound of the present invention；
In the step f, the condition of reaction are as follows: reacted 20 hours or more at 70 DEG C；
Its general structure of the compound being prepared is as follows:
R is fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group or phenyl in logical formula (I), and R is that a substitution or two take
Generation.
The acetophenone derivs are 3,4- dichloroacetophenone, 3- bromoacetophenone, 3- chloro-acetophenone, biphenyl list ethyl ketone, 4- fluorobenzene
One of ethyl ketone；
In the step b, reaction temperature is 0-5 DEG C.
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