CN105175312A - 1-substituted-2-(carbazole-9-yl-acetic acid)-hydrazide Schiff base and preparation method thereof - Google Patents
1-substituted-2-(carbazole-9-yl-acetic acid)-hydrazide Schiff base and preparation method thereof Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The invention provides 1-substituted-2-(carbazole-9-yl-acetic acid)-hydrazide Schiff base and a preparation method thereof. The preparation method comprises the following steps: adding 9-carbazole acethydrazide, aldehyde and p-toluene sulfonic acid into a dry reaction container, uniformly grinding the mixture, carrying out an insulation reaction, carrying out a post-treatment on the product to obtain the 1-substituted-2-(carbazole-9-yl-acetic acid)-hydrazide Schiff base. According to the preparation method, the 1-substituted-2-(carbazole-9-yl-acetic acid)-hydrazide Schiff base is prepared by using various aldehyde compounds and 9-carbazole acethydrazide as raw materials and the p-toluene sulfonic acid as a catalyst by adopting a solid-phase solvent-free method. The method has the advantages of short reaction time, no solvent, simple operation process, mild reaction condition, low equipment requirement, simple post-treatment and complete reaction, and has a yield of over 95 percent. The 1-substituted-2-(carbazole-9-yl-acetic acid)-hydrazide Schiff base prepared by the method has an excellent antibacterial effect.
Description
Technical field
The invention belongs to the field of chemical synthesis, particularly 1-replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff and preparation method thereof.
Background technology
Carbazole is a kind of important azaaromatics, containing larger conjugated system and strong cyclic voltammetry method in molecule, has stronger electron donation and cavity transmission ability, and has higher thermostability and photochemical stability; Its derivative has potential widespread use in fields such as photoelectric material, dyestuff, medicine, Supramolecular Recognition, chemical sensitisations.Itself be one of coal-tar products, raw material is easy to get.Carbazyl is introduced different molecules, with its synthesis new containing carbazyl or the compound with property be a study hotspot of carbazole in recent years.
Schiff is the organic compound that a class contains imines or azomethine characteristic group (>C=N-or-CR=N-).There is due to it features such as stronger coordination ability, various coordination mode, widely biological activity and good optical property, be widely applied in medicine, catalysis and functional materials etc.Schiff all receives much concern for a long time.Because containing >C=N-structure in its basic structure, the atom N on its heterocycle track has lone-pair electron, thus imparts the meaning on its important chemistry and biology.
The method of traditional synthesis Schiff is the method adopting liquid phase synthesis, and generally using ethanol as solvent, traditional synthetic method, complicated operation, equipment requirements is high, and the time is long, takes time and effort, and productive rate is very low.And the Schiff of carbazolyl-containing becomes the brand-new field of of research, have no bibliographical information at present and adopt polishing, both combined by chemical process, to obtaining the superposition of its performance, therefore the research of this respect is also a focus of chemist research.
Summary of the invention
The object of the present invention is to provide a kind of 1-to replace-2-(carbazole-9-base-acetic acid)-hydrazides class Schiff and preparation method thereof, the method reaction times is short, without the need to solvent, operating process is simple, and reaction conditions is gentle, and equipment requirements is low, aftertreatment is simple, and react completely, productive rate is high.
For achieving the above object, the present invention adopts following technical scheme:
1-replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, and its structural formula is as follows:
Wherein R is
or H; R' is H, 4-CH
3, 4-F, 4-Cl, 4-Br, 4-CH
3o, 4-N
2o, 4-N-(CH
3)
2, 3-NO
2, or 4-OH.
1-replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, comprises the following steps:
1) in the reaction vessel of drying, add the 9-carbazole acethydrazide of Amol, the aldehyde material of Bmol and the p-methyl benzenesulfonic acid of Cmol, grinding evenly, obtains mixture; Wherein A:B:C=1:(1 ~ 1.2): (1 ~ 1.2);
2) by mixture insulation reaction 1 ~ 1.5h, then naturally cooling at 75 ~ 80 DEG C, then reaction product is washed, suction filtration, by filter cake recrystallization, namely obtain 1-replace-2-(carbazole-9-base-acetic acid)-hydrazides Schiff.
Described aldehyde material is formaldehyde, cinnamic aldehyde, 2 thiophene carboxaldehyde, 3-thiophenecarboxaldehyde, furfural, withered name aldehyde, pyridine-2-formaldehyde, phenyl aldehyde, 4-chloro-benzaldehyde, p-bromobenzaldehyde, p-Fluorobenzenecarboxaldehyde, paranitrobenzaldehyde, p-tolyl aldehyde, aubepine, Ortho Nitro Benzaldehyde, 3-nitrobenzaldehyde, p-Hydroxybenzaldehyde or paradimethy laminobenzaldehyde.
Described reaction vessel is mortar.
Described step 1) in grinding evenly required time be 5 ~ 15min.
Described step 1) in grinding at room temperature carry out.
Described step 2) in insulation reaction carry out in an oven.
Described step 2) in washing reaction product time solvent used to be volume fraction be 90 ~ 95% ethanol.
Described step 2) in recrystallization solvent used be dehydrated alcohol.
Compared with prior art, beneficial effect of the present invention is:
1-provided by the invention replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, with 9-carbazole acethydrazide and aldehyde material for raw material, take p-methyl benzenesulfonic acid as catalyzer, adopt solid phase solventless method to prepare 1-by grinding and replace-2-(carbazole-9-base-acetic acid)-hydrazides Schiff.Polishing utilizes the mechanical force of mortar and pestle generation in reactant, and a kind of solid phase reaction method that reaction is carried out, its and easy handling more more convenient than traditional methodology of organic synthesis, under grinding condition, many traditional reactions can be carried out under relatively mild condition, or improve yield or Reaction time shorten, even can cause the reaction that some can not carry out under conventional conditions.The catalyzer that the present invention adopts is p-methyl benzenesulfonic acid, adopts solid acid as catalyst can avoid the shortcoming of traditional method, has that reactive behavior is high, speed of response is fast, the reaction times is short, good selective.Not only can overcome the vitriol oil as the shortcoming such as etching apparatus, contaminate environment during catalyzer, and catalyzer can be reused, utilization ratio is improved.The present invention prepares 1-by solid state reaction and replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, speed of response is fast, reaction times is short, without the need to solvent, operating process is simple, only even for raw mill rear held for some time need be got final product complete reaction, reaction conditions is gentle, equipment requirements is low, aftertreatment is simple, react completely, obtained 1-replaces the productive rate of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff up to more than 97%, overcome long reaction time in conventional heating methods, solvent load is large, the shortcomings such as aftertreatment is difficult, a kind of green, environmental protection, fast, efficiently, the easy method preparing 1-replacement-2-(carbazole-9-base-acetic acid)-hydrazides Schiff.
1-provided by the invention replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff and includes the Schiff that more than ten plant the carbazolyl-containing without report, and tested by bacteriostatic experiment, find that 1-provided by the invention replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff and all has good fungistatic effect, therefore the present invention can provide useful help for the development and application of the Schiff compounds of carbazolyl-containing.
Accompanying drawing explanation
Fig. 1 is the infared spectrum of the 9-carbazole acethydrazide contracting p-tolyl aldehyde Schiff that embodiment 1 obtains;
Fig. 2 is the nuclear magnetic resonance map of the 9-carbazole acethydrazide contracting p-tolyl aldehyde Schiff that embodiment 1 obtains;
Fig. 3 is the infared spectrum of the 9-carbazole hydrazides formal Schiff that embodiment 2 obtains;
Fig. 4 is the nuclear magnetic resonance map of the 9-carbazole hydrazides formal Schiff that embodiment 2 obtains;
Fig. 5 is the infared spectrum of the 9-carbazole acethydrazide contracting aubepine Schiff that embodiment 3 obtains;
Fig. 6 is the nuclear magnetic resonance map of the 9-carbazole acethydrazide contracting aubepine Schiff that embodiment 3 obtains.
Embodiment
The present invention for raw material, take p-methyl benzenesulfonic acid as catalyzer with 9-carbazole hydrazides and various aldehydes, and reaction generates 1-and replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, and its reaction equation is:
Wherein R is
or H; R' is H, 4-CH
3, 4-F, 4-Cl, 4-Br, 4-CH
3o, 4-N
2o, 4-N-(CH
3)
2, 3-NO
2or 4-OH.
Below in conjunction with preferred embodiment of the present invention, the present invention is described in further details.
Embodiment 1
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the p-tolyl aldehyde of 0.0002mol and the p-methyl benzenesulfonic acid of 0.0002mol, grind 5min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1h at the temperature of 80 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 95%, the filter cake obtained is green solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting p-tolyl aldehyde Schiff, productive rate is 98%.
Fig. 1 is the infared spectrum of the 9-carbazole acethydrazide contracting p-tolyl aldehyde Schiff that embodiment 1 obtains, as can be seen from Figure 1, at 3420cm
-1the absorption peak of left and right is the vibration absorption peak of N-H; 3049cm
-1place is the stretching vibration absorption peak of phenyl ring C-H; Appear at 2822cm
-1the characteristic peak at left and right place is the absorption peak of the methylene radical on saturated C-H and carbazole ring; At 1679cm
-1left and right place is the vibration absorption peak of C=O; At 1598cm
-1place has very strong absorption vibration peak to produce, and the NH on C=O and hydrazides on aldehyde is described
2carry out condensation reaction, produce C=N group; Phenyl ring skeletal vibration absorption peak appears at 1598cm
-1, 1491cm
-1and 1438cm
-1; Stretching vibration absorption peak (acid amides II bands of a spectrum) in N-H flexural vibration and C-N face overlaps with phenyl ring skeletal vibration absorption peak.Appear at 813cm
-1and 747cm
-1the more weak absorption peak that left and right goes out, for phenyl ring replaces the vibration stretching absorbance peak produced.More than illustrate that 9-carbazole acethydrazide and p-tolyl aldehyde react and generate 9-carbazole acethydrazide contracting p-tolyl aldehyde Schiff.
Fig. 2 is the nuclear magnetic resonance map of the 9-carbazole acethydrazide contracting p-tolyl aldehyde Schiff that embodiment 1 obtains, and as seen from Figure 2, the chemical shift of the H on phenyl ring on methyl group appears at 2.42 – 2.31ppm, and is multiplet; Appear at the signal that 5.45ppm place is the proton on the-CH2-that connects of the carbazole group of schiff bases; On aromatic ring, the chemical shift of H appears between 7.13 ~ 7.80ppm, and the chemical shift of the H on-NHCO-is 9.85ppm; By the impact of-C=N-key, appear at the chemical shift of the bimodal H for being connected with-C=N-key at 8.00ppm place.Prove thus to have synthesized this type of Schiff.
Embodiment 2
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the formaldehyde of 0.0002mol and the p-methyl benzenesulfonic acid of 0.0002mol, grind 10min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1h at the temperature of 80 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 95%, the filter cake obtained is white solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole hydrazides formal Schiff, productive rate is 97.5%.
Fig. 3 is the infared spectrum of the 9-carbazole hydrazides formal Schiff that embodiment 2 obtains, as can be seen from Figure 3, at 3410cm
-1left and right place goes out peak, is N-H stretching vibration absorption peak; 3049cm
-1place is the stretching vibration absorption peak of phenyl ring C-H; The absorption peak of the methylene radical on saturated C-H and carbazole ring appears at 2822cm
-1place; At 1660cm
-1place has stronger absorption vibration absorption peak to exist, and is illustrated as the stretching vibration charateristic avsorption band (acid amides I bands of a spectrum) of C=O; At 1598cm
-1place has very strong absorption vibration peak to produce, and the NH on C=O and hydrazides on aldehyde is described
2carry out condensation reaction, produce C=N group; Phenyl ring skeletal vibration absorption peak appears at 1598cm
-1, 1486cm
-1, 1334cm
-1and 1208cm
-1; Stretching vibration absorption peak (acid amides II bands of a spectrum) in N-H flexural vibration and C-N face overlaps with phenyl ring skeletal vibration absorption peak.9-carbazole acethydrazide and formaldehyde condensation reaction success are more than described, obtain 9-carbazole acethydrazide formal Schiff.
Fig. 4 is the nuclear magnetic resonance map of the 9-carbazole hydrazides formal Schiff that embodiment 2 obtains, and the signal of the proton on the-CH2-of the carbazole group connection of schiff bases as seen from Figure 4 appears at 4,94ppm place; On aromatic ring, the chemical shift of H appears between 7.10 ~ 7.89ppm, and the chemical shift of the H on-NHCO-is 9.59ppm; By the impact of-C=N-key, the chemical shift of the H be connected with-C=N-key appears at 7.01ppm place.Prove thus to have synthesized this type of material.
Embodiment 3
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the aubepine of 0.0002mol and the p-methyl benzenesulfonic acid of 0.00024mol, grind 10min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is sapphirine solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting aubepine Schiff, productive rate is 99%.
Fig. 5 is the infared spectrum of the 9-carbazole acethydrazide contracting aubepine Schiff that embodiment 3 obtains, as can be seen from Figure 5, at 3410cm
-1left and right place goes out peak, is N-H stretching vibration absorption peak; 3050cm
-1place is the stretching vibration absorption peak of phenyl ring C-H; The absorption peak of the methylene radical on saturated C-H and carbazole ring appears at 2831cm
-1place; At 1679cm
-1place has stronger absorption vibration absorption peak to exist, and is illustrated as the stretching vibration charateristic avsorption band (acid amides I bands of a spectrum) of C=O; At 1597cm
-1place has very strong absorption vibration peak to produce, and the NH on C=O and hydrazides on aldehyde is described
2carry out condensation reaction, produce C=N group; Phenyl ring skeletal vibration absorption peak appears at 1597cm
-1, 1505cm
-1and 1455cm
-1; Stretching vibration absorption peak (acid amides II bands of a spectrum) in N-H flexural vibration and C-N face overlaps with phenyl ring skeletal vibration absorption peak; Appear at 1250cm
-1stretching vibration peak be the absorption vibration peak of C-O-C; 1250cm
-1, 1170m
-1and 834cm
-1the vibration absorption peak of left and right is-CH
3charateristic avsorption band; 827cm
-1and 748cm
-1for the mono-substituted characteristic peak of phenyl ring.9-carbazole acethydrazide and aubepine condensation reaction success are more than described, obtain 9-carbazole acethydrazide contracting aubepine Schiff.
Fig. 6 is the nuclear magnetic resonance map of the 9-carbazole acethydrazide contracting aubepine Schiff that embodiment 3 obtains, and the chemical shift of the H as seen from Figure 6 on phenyl ring on methoxyl group appears at 4.36ppm place; The signal of the proton on the-CH2-of the carbazole group connection of schiff bases appears at 5,67ppm place; On aromatic ring, the chemical shift of H appears between 7.10 ~ 7.89ppm, and the chemical shift of the H on-NHCO-is 9.28ppm; By the impact of-C=N-key, the chemical shift of the H be connected with-C=N-key appears at 8.12-7.92ppm place.Prove thus to have synthesized this type of material.
Embodiment 4
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the pyridine-2-formaldehyde of 0.0002mol and the p-methyl benzenesulfonic acid of 0.00024mol, grind 15min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is yellow solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting pyridine-2-formaldehyde Schiff, productive rate is 95%.
IR(KBr),ν/cm
-1:3417,3050,2860,2772,1696,1595,1580,1454,1321,1237,999,928,848,744,721。
Embodiment 5
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the 2 thiophene carboxaldehyde of 0.0002mol and the p-methyl benzenesulfonic acid of 0.00024mol, grind 10min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is gray solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting 2 thiophene carboxaldehyde Schiff, productive rate is 95%.
IR(KBr),ν/cm
-1:3416,3051,2862,2772,1681,1619,1535,1495,1450,1319,1286,1240,998,848,741。
Embodiment 6
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the furfural of 0.0002mol and the p-methyl benzenesulfonic acid of 0.00022mol, grind 10min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is black solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide furfural Schiff, productive rate is 92%.
IR(KBr),ν/cm
-1:3417,3050,2880,2772,1655,1546,1501,1498,1436,1325,1275,1201,1198,1005,990,885,845,742,721。
Embodiment 7
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the withered name aldehyde of 0.0002mol and the p-methyl benzenesulfonic acid of 0.00024mol, grind 15min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is dark green solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide and to contract withered name aldehyde Schiff, productive rate is 95%.
IR(KBr),ν/cm
-1:3397,3042,2866,2771,1701,1689,1516,1489,1456,1314,1265,1201,1128,1004,993,845,742,721。
Embodiment 8
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the cinnamic aldehyde of 0.0002mol and the p-methyl benzenesulfonic acid of 0.00024mol, grind 15min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is greyish-green solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting cinnamic aldehyde Schiff, productive rate is 97%.
IR(KBr),ν/cm
-1:3397,3050,2865,2771,1682,1621,1528,1505,1491,1485,1316,1237,1126,993,880,842,746,721。
Embodiment 9
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the p-Fluorobenzenecarboxaldehyde of 0.00024mol and the p-methyl benzenesulfonic acid of 0.00024mol, grind 8min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.2h at the temperature of 78 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is white solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting p-Fluorobenzenecarboxaldehyde Schiff, productive rate is 97%.
IR (KBr compressing tablet), ν/cm
-1: 3421,3192,3097,2967,2772,1679,1600,1497,1458,135,1278,1228,1152,999,838,742.
Embodiment 10
1) in the mortar of drying, add the 9-carbazole acethydrazide of 0.0002mol, the paranitrobenzaldehyde of 0.00022mol and the p-methyl benzenesulfonic acid of 0.00022mol, grind 12min under room temperature to evenly, obtain mixture.
2) mixture is placed in baking oven, insulation reaction 1.5h at the temperature of 75 DEG C, after thing naturally cooling to be mixed, with washing with alcohol, suction filtration that volumetric concentration is 90%, the filter cake obtained is yellow solid, filter cake is used dehydrated alcohol recrystallization, obtain 9-carbazole acethydrazide contracting paranitrobenzaldehyde Schiff, productive rate is 94%.
IR (KBr compressing tablet), ν/cm
-1: 3417,3190,3083,2970,2848,2773,1683,1520,1458,1424,1336,1270,1206,1142,1105,1004,889,842,748,659.
In addition to the implementation, also the aldehyde material such as available 3-thiophenecarboxaldehyde, phenyl aldehyde, 4-chloro-benzaldehyde, p-bromobenzaldehyde, Ortho Nitro Benzaldehyde, 3-nitrobenzaldehyde, p-Hydroxybenzaldehyde, paradimethy laminobenzaldehyde reacts as reactant.
The 1-obtained the present invention replaces the test that-2-(carbazole-9-base-acetic acid)-hydrazides Schiff has been carried out for Gram-negative bacteria and E. coli Activity, finds that its inhibiting rate reaches more than 70%.Known by the comparative analysis 1-containing different substituents being replaced to-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, 1-replacement-2-(carbazole-9-base-acetic acid)-hydrazides Schiff being connected with aliphatic group is all better to colibacillary activity, inhibiting rate is between 70 ~ 90%, especially electron-withdrawing group is stronger, and inhibiting rate is higher; Substituent 1-containing heterocycle replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff to colibacillary inhibiting rate between 75 ~ 80%.Illustrate that 1-replacement-2-(carbazole-9-base-acetic acid)-hydrazides Schiff that the present invention obtains has good fungistatic effect.
Claims (9)
1.1-replaces-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, and it is characterized in that, its structural formula is as follows:
Wherein R is
or H; R' is H, 4-CH
3, 4-F, 4-Cl, 4-Br, 4-CH
3o, 4-N
2o, 4-N-(CH
3)
2, 3-NO
2, or 4-OH.
2. 1-according to claim 1 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that, comprises the following steps:
1) in the reaction vessel of drying, add the 9-carbazole acethydrazide of Amol, the aldehyde material of Bmol and the p-methyl benzenesulfonic acid of Cmol, grinding evenly, obtains mixture; Wherein A:B:C=1:(1 ~ 1.2): (1 ~ 1.2);
2) by mixture insulation reaction 1 ~ 1.5h, then naturally cooling at 75 ~ 80 DEG C, then reaction product is washed, suction filtration, by filter cake recrystallization, namely obtain 1-replace-2-(carbazole-9-base-acetic acid)-hydrazides Schiff.
3. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described aldehyde material is formaldehyde, cinnamic aldehyde, 2 thiophene carboxaldehyde, 3-thiophenecarboxaldehyde, furfural, withered name aldehyde, pyridine-2-formaldehyde, phenyl aldehyde, 4-chloro-benzaldehyde, p-bromobenzaldehyde, p-Fluorobenzenecarboxaldehyde, paranitrobenzaldehyde, p-tolyl aldehyde, aubepine, Ortho Nitro Benzaldehyde, 3-nitrobenzaldehyde, p-Hydroxybenzaldehyde or paradimethy laminobenzaldehyde.
4. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described reaction vessel is mortar.
5. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described step 1) in grinding evenly required time be 5 ~ 15min.
6. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described step 1) in grinding at room temperature carry out.
7. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described step 2) in insulation reaction carry out in an oven.
8. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described step 2) in washing reaction product time solvent used to be volume fraction be 90 ~ 95% ethanol.
9. 1-according to claim 2 replaces the preparation method of-2-(carbazole-9-base-acetic acid)-hydrazides Schiff, it is characterized in that: described step 2) in recrystallization solvent used be dehydrated alcohol.
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