CN104098610A - Method for preparing hydrazine Schiff alkali substituted by 1-phenyl-5-diferrocenyl-1,3-pentadiene-5-ketal - Google Patents

Method for preparing hydrazine Schiff alkali substituted by 1-phenyl-5-diferrocenyl-1,3-pentadiene-5-ketal Download PDF

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CN104098610A
CN104098610A CN201410366596.7A CN201410366596A CN104098610A CN 104098610 A CN104098610 A CN 104098610A CN 201410366596 A CN201410366596 A CN 201410366596A CN 104098610 A CN104098610 A CN 104098610A
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phenyl
pentadiene
ferrocenyl
contracting
ketone
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刘玉婷
宋思梦
尹大伟
殷艳佼
刘蓓蓓
杨阿宁
王金玉
吕博
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Shaanxi University of Science and Technology
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Shaanxi University of Science and Technology
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Abstract

A method for preparing hydrazine Schiff alkali substituted by 1-phenyl-5-diferrocenyl-1,3-pentadiene-5-ketal comprises the following steps: 1) adding A mmol of 1-phenyl-5-diferrocenyl-1,3-pentadiene ketone, B mmol of thiosemicarbazide and C mL of anhydrous ethanol into a reaction vessel, wherein A:B:C=1:(1-1.2):(5-6), mixing until dissolving, and adjusting the pH value of the reaction system to maintain a weak acid environment; 2) performing reaction under microwave for 3-5 min, cooling to the room temperature when the reaction is complete, and separating the solid to obtain the hydrazine Schiff alkali substituted by 1-phenyl-5-diferrocenyl-1,3-pentadiene-5-ketal. The method adopts the microwave reaction, is short in reaction time, moderate in reaction condition, and simple in operation, has a yield higher than 75%, and is an environment-friendly, economical and efficient method for synthesizing ferrocenyl chalcone Schiff alkali.

Description

A kind of method of preparing 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting replacement hydrazine Schiff alkali
Technical field
The invention belongs to the field of chemical synthesis, particularly a kind of method of preparing 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting replacement hydrazine Schiff alkali.
Background technology
In recent years, more and more cause people's interest as the biferrocenyl chalcone derivative of important organic synthesis intermediate.Biferrocenyl chalcone is made by conventional heating method in ethanol by ferrocenyl methyl ketone and aromatic aldehyde conventionally.Nineteen ninety, Toma etc. have reported that ground force etc. have reported under microwave radiation condition and made catalyzer with KF-Al2O3, make ferrocenyl methyl ketone and aromatic aldehyde dry process reaction synthesize biferrocenyl chalcone taking 18-hat-6 as phase-transfer catalyst.All there are some shortcomings in these methods, or is long reaction time, or be to use a large amount of organic solvents, or be post-processing operation complexity.
Since Gedye equal 1986 by microwave radiation for organic synthesis since, microwave technology is widely used in organic synthesis.
Summary of the invention
The object of the invention is to overcome above-mentioned the problems of the prior art, a kind of method that method is simple to operate, the reaction times is short, 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting replacement hydrazine Schiff alkali is simply prepared in aftertreatment is provided.
For achieving the above object, the present invention adopts following technical scheme:
1) in reaction vessel, add A mmol1-phenyl-5-ferrocenyl-pentadienone, B mmol thiosemicarbazide and C mL dehydrated alcohol, wherein A:B:C=1:(1～1.2): (5～6), stirring is dissolved it, regulates the pH value of reaction system to make it maintain slightly acidic;
2) under microwave, react 3～5min, after having reacted, be chilled to room temperature, isolate solid, obtain the contracting of 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone and replace hydrazine Schiff alkali.
Described step 1) reaction vessel be single port container.
The chemical formula of described replacement hydrazine is NH 2nHCS-R, wherein comprise-NH of R base 2,-SCH 3,-SCH 2ph ,-CH 2cH 3,-CH 2cH 2cH 3or-CH 2cH 2cH 2cH 3.
Described step 1) in pH value to 4～6 of dense HCl regulation system.
Described step 2) in microwave irradiation be to irradiate once every 30s under 350～400W.
Described step 2) in be separated into, cooledly reaction solution is concentrated into dry, obtain crude product, then crude product is carried out to recrystallization, obtain the contracting of sterling 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone and replace hydrazine Schiff alkali.
Described step 2) in recrystallization solvent for use be dehydrated alcohol.
The structural formula that 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting of described preparation replaces hydrazine Schiff alkali is:
Wherein comprise-NH of R base 2,-SCH 3,-SCH 2ph ,-CH 2cH 3,-CH 2cH 2cH 3or-CH 2cH 2cH 2cH 3.
Compared with prior art, beneficial effect of the present invention is:
1-phenyl-5-provided by the invention ferrocenyl-1, the contracting of 3-pentadiene-5-ketone replaces the preparation method of hydrazine Schiff alkali, taking 1-phenyl-5-ferrocenyl-pentadienone and replace hydrazine as raw material, dehydrated alcohol is solvent, adopt microwave method to prepare the contracting of 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone and replace hydrazine Schiff alkali.Compared with traditional liquid-phase reflux method, the more convenient and easy handling of microwave method.The present invention prepares 1-phenyl-5-ferrocenyl-1 by microwave reaction, the contracting of 3-pentadiene-5-ketone replaces hydrazine Schiff alkali, reaction process is simple, simple to operate, reaction times foreshortens to 3～5min by 5～6h of routine, reaction times is short, greatly improve speed of reaction, it is low that p-methyl benzenesulfonic acid has toxicity as catalyzer, advantage cheap and easy to get, and the aftertreatment of the method is simple, 1-phenyl-5-ferrocenyl-1, the contracting of 3-pentadiene-5-ketone replaces the productive rate of hydrazine Schiff alkali up to more than 80%, overcome long reaction time in conventional heating method, the shortcomings such as aftertreatment difficulty, a kind of green, economical, convenient, efficiently, hypotoxic preparation method.
1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone provided by the invention contracting replaces hydrazine Schiff alkali and is brand-new compound, has no bibliographical information mistake, can be used for antibacterial, anti-inflammatory etc.
Embodiment
The present invention is taking 1-phenyl-5-ferrocenyl-pentadienone and replace hydrazine as raw material, dehydrated alcohol is solvent, and dense HCl is acid regulator, and reaction generates 1-phenyl-5-ferrocenyl-1, the contracting of 3-pentadiene-5-ketone replaces hydrazine Schiff alkali, and its reaction equation is suc as formula shown in (1).
Wherein R base is-NH 2,-SCH 3,-SCH 2ph ,-CH 2cH 3,-CH 2cH 2cH 3or-CH 2cH 2cH 2cH 3deng.
Preparation method's of the present invention concrete steps comprise:
1) in the round-bottomed flask of single port, add A mmol1-phenyl-5-ferrocenyl-pentadienone, B mmol thiosemicarbazide and C mL dehydrated alcohol, wherein A:B:C=1:(1～1.2): (5～6), stirring make its dissolve, with the pH of dense HCl regulation system to slightly acidic.
2) round-bottomed flask is placed in to microwave reaction kettle, under 350～400W, irradiate once every 30s, reaction 3～5min, after having reacted, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then with low price and the little dehydrated alcohol of toxicity, crude product is carried out to recrystallization, obtain the contracting of sterling 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone and replace hydrazine Schiff alkali.
Below in conjunction with preferred embodiment of the present invention, the present invention is described in further details.
Embodiment 1
1) 1-phenyl-5-ferrocenyl-pentadienone, the 1mmol thiosemicarbazide of getting 1mmol join in dry 250mL single port flask, then add 5mL dehydrated alcohol, stir it dissolved, with the pH of dense HCl regulation system be slightly acidic.
2) round-bottomed flask is placed in to microwave reaction kettle, under 350W, irradiates once every 30s, irradiation duration is 3min.Irradiate completely, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then uses dehydrated alcohol recrystallization, obtains sterling.Productive rate 82.7%.m.p.132～135℃。
IR (KBr compressing tablet, v/cm -1): 3088,1502,1110 (Fc rings); 3026 (Ar-H); 1680 (C=N) 1613,1621 (C=C); 692,673,671 (Ar-H).
1hNMR (CDCl 3, 400MHz, mark in TMS, δ: ppm): 7.20-7.35 (m, 5H, ArH), 4.34 (s, 5H, C 5h 5), 4.51 (s, 2H, C 5h 4), 4.52 (s, 2H, C 5h 4), 7.51 (s, H, NH), 6.50 (s, 2H, NH 2), 5.85 (d, H ,=CH), 6.12 (d, H ,=CH).
Ultimate analysis: C 22h 21feN 3s measured value (calculated value): C 63.71 (63.62); H 5.02 (5.10); N 10.06 (10.12).
Embodiment 2
1) 1-phenyl-5-ferrocenyl-pentadienone, the 1.3mmol Methyl hydrazinecarbodithioate of getting 1mmol join in dry 250mL single port flask, then add 5mL dehydrated alcohol, stir it dissolved, with the pH of dense HCl regulation system be slightly acidic.
2) round-bottomed flask is placed in to microwave reaction kettle, under 400W, irradiates once every 30s, irradiation duration is 3min.Irradiate completely, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then uses dehydrated alcohol recrystallization, obtains sterling.Productive rate 82.3%.m.p.126～127℃。
IR (KBr compressing tablet, v/cm -1): 3080,1513,1125 (Fc rings); 3029 (Ar-H); 1671 (C=N) 1612,1620 (C=C); 682,671 (Ar-H).
1hNMR (CDCl 3, 400MHz, mark in TMS, δ: ppm): 7.18-7.35 (m, 5H, ArH), 4.31 (s, 5H, C 5h 5), 4.52 (s, 2H, C 5h 4), 4.60 (s, 2H, C 5h 4), 7.85 (s, H, NH), 3.12 (s, 3H, CH 3), 5.71 (d, H ,=CH), 6.05 (d, H ,=CH).
Ultimate analysis: C 23h 22feN 2s 2measured value (calculated value): C 61.76 (61.88); H 5.06 (4.97); N 6.35 (6.28).
Embodiment 3
1) 1-phenyl-5-ferrocenyl-pentadienone, the 1mmol S-benzyldithiocarbazate of getting 1mmol join in dry 250mL single port flask, then add 5mL dehydrated alcohol, stir it dissolved, with the pH of dense HCl regulation system be slightly acidic.
2) round-bottomed flask is placed in to microwave reaction kettle, under 380W, irradiates once every 30s, irradiation duration is 3min.Irradiate completely, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then uses dehydrated alcohol recrystallization, obtains sterling.Productive rate 80.7%.m.p.142～145℃。
IR (KBr compressing tablet, v/cm -1): 3071,1505,1120 (Fc rings); 3053 (Ar-H); 1662 (C=N) 1610,1631 (C=C); 702,725 (Ar-H).
1hNMR (CDCl 3, 400MHz, mark in TMS, δ: ppm): 7.20-7.32 (m, 10H, ArH), 4.31 (s, 5H, C 5h 5), 4.48 (s, 2H, C 5h 4), 4.62 (s, 2H, C 5h 4), 7.81 (s, H, NH), 4.12 (s, 2H, CH 2), 5.78 (d, H ,=CH), 6.23 (d, H ,=CH).
Ultimate analysis: C 29h 26feN 2s 2measured value (calculated value): C 66.75 (66.66); H 5.11 (5.02); N 5.23 (5.36).
Embodiment 4
1) the 1-phenyl-5-ferrocenyl-pentadienone, 1.1mmol of getting 1mmol replace hydrazine and join in dry 250mL single port flask, and the chemical formula that wherein replaces hydrazine is NH 2nHCS-CH 2cH 3, then add 6mL dehydrated alcohol, stir make its dissolve, with the pH value of dense HCl regulation system be 4.
2) round-bottomed flask is placed in to microwave reaction kettle, under 370W, irradiates once every 30s, irradiation duration is 4min.Irradiate completely, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then uses dehydrated alcohol recrystallization, obtains sterling.Productive rate 76.6%.m.p.109～110℃。
IR (KBr compressing tablet, v/cm -1): 3090,1521,1130 (Fc rings); 3030 (Ar-H); 1680 (C=N) 1613,1621 (C=C); 692,673,669 (Ar-H).
1hNMR (CDCl 3, 400MHz, mark in TMS, δ: ppm): 7.20-7.35 (m, 5H, ArH), 4.34 (s, 5H, C 5h 5), 4.45 (s, 2H, C 5h 4), 4.54 (s, 2H, C 5h 4), 7.50 (s, H, NH), 2.30 (m, 2H, CH 2), 0.96 (m, 3H, CH 3), 5.85 (d, H ,=CH), 6.10 (d, H ,=CH).
Ultimate analysis: C 24h 24feN 2s measured value (calculated value): C 77.42 (77.41); H 6.45 (6.46); N 7.53 (7.52).
Embodiment 5
1) the 1-phenyl-5-ferrocenyl-pentadienone, 1.2mmol of getting 1mmol replace hydrazine and join in dry 250mL single port flask, and the chemical formula that wherein replaces hydrazine is NH 2nHCS-CH 2cH 2cH 3, then add 5.5mL dehydrated alcohol, stir make its dissolve, with the pH value of dense HCl regulation system be 5.
2) round-bottomed flask is placed in to microwave reaction kettle, under 360W, irradiates once every 30s, irradiation duration is 5min.Irradiate completely, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then uses dehydrated alcohol recrystallization, obtains sterling.Productive rate 78.2%.m.p.117～119℃。
IR (KBr compressing tablet, v/cm -1): 3080,1525,1138 (Fc rings); 3027 (Ar-H); 1676 (C=N) 1615,1620 (C=C); 692,675,675 (Ar-H).
1hNMR (CDCl 3, 400MHz, mark in TMS, δ: ppm): 7.20-7.35 (m, 5H, ArH), 4.34 (s, 5H, C 5h 5), 4.45 (s, 2H, C 5h 4), 4.54 (s, 2H, C 5h 4), 7.50 (s, H, NH), 2.32-2.38 (m, 4H, CH 2), 1.02 (m, 3H, CH 3), 5.85 (d, H ,=CH), 6.10 (d, H ,=CH).
Ultimate analysis: C 25h 26feN 2s measured value (calculated value): C 77.72 (77.72); H 6.73 (6.74); N 7,26 (7.25).
Embodiment 6
1) the 1-phenyl-5-ferrocenyl-pentadienone, 1.3mmol of getting 1mmol replace hydrazine and join in dry 250mL single port flask, and the chemical formula that wherein replaces hydrazine is NH 2nHCS-CH 2cH 2cH 2cH 3, then add 6mL dehydrated alcohol, stir make its dissolve, with the pH value of dense HCl regulation system be 6.
2) round-bottomed flask is placed in to microwave reaction kettle, under 390W, irradiates once every 30s, irradiation duration is 4min.Irradiate completely, be chilled to room temperature, filtrate is concentrated into dry, obtains crude product, then uses dehydrated alcohol recrystallization, obtains sterling.Productive rate 79.8%.m.p.123～125℃。
IR (KBr compressing tablet, v/cm -1): 3075,1525,1142 (Fc rings); 3024 (Ar-H); 1680 (C=N) 1615,1624 (C=C); 692,675,675 (Ar-H).
1hNMR (CDCl 3, 400MHz, mark in TMS, δ: ppm): 7.23-7.34 (m, 5H, ArH), 4.35 (s, 5H, C 5h 5), 4.48 (s, 2H, C 5h 4), 4.57 (s, 2H, C 5h 4), 7.51 (s, H, NH), 2.29-2.36 (m, 6H, CH 2), 1.08 (m, 3H, CH 3), 5.83 (d, H ,=CH), 6.08 (d, H ,=CH).
Ultimate analysis: C 22h 21feN 3s measured value (calculated value): C 63.71 (63.62); H 5.02 (5.10); N 10.06 (10.12).

Claims (8)

1. prepare the method that the contracting of 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone replaces hydrazine Schiff alkali, it is characterized in that, comprise the following steps:
1) in reaction vessel, add A mmol1-phenyl-5-ferrocenyl-pentadienone, B mmol thiosemicarbazide and C mL dehydrated alcohol, wherein A:B:C=1:(1～1.2): (5～6), stirring is dissolved it, regulates the pH value of reaction system to make it maintain slightly acidic;
2) under microwave, react 3～5min, after having reacted, be chilled to room temperature, isolate solid, obtain the contracting of 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone and replace hydrazine Schiff alkali.
2. a kind of method that 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting replaces hydrazine Schiff alkali of preparing according to claim 1, is characterized in that: described step 1) reaction vessel be single port container.
3. a kind of method that the contracting of 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone replaces hydrazine Schiff alkali of preparing according to claim 1, is characterized in that: the chemical formula of described replacement hydrazine is NH 2nHCS-R, wherein comprise-NH of R base 2,-SCH 3,-SCH 2ph ,-CH 2cH 3,-CH 2cH 2cH 3or-CH 2cH 2cH 2cH 3.
4. prepare according to a kind of described in claim 1-3 any one the method that the contracting of 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone replaces hydrazine Schiff alkali, it is characterized in that: described step 1) in pH value to 4～6 of dense HCl regulation system.
5. a kind of method that 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting replaces hydrazine Schiff alkali of preparing according to claim 4, is characterized in that: described step 2) in microwave irradiation be to irradiate once every 30s under 350～400W.
6. one according to claim 1 is prepared 1-phenyl-5-ferrocenyl-1, the contracting of 3-pentadiene-5-ketone replaces the method for hydrazine Schiff alkali, it is characterized in that: described step 2) in be separated into, cooled reaction solution is concentrated into dry, obtain crude product, then crude product is carried out to recrystallization, obtain the contracting of sterling 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone and replace hydrazine Schiff alkali.
7. a kind of method that 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting replaces hydrazine Schiff alkali of preparing according to claim 6, is characterized in that: described step 2) in recrystallization solvent for use be dehydrated alcohol.
8. one according to claim 1 is prepared 1-phenyl-5-ferrocenyl-1, the contracting of 3-pentadiene-5-ketone replaces the method for hydrazine Schiff alkali, it is characterized in that: the structural formula that 1-phenyl-5-ferrocenyl-1,3-pentadiene-5-ketone contracting of described preparation replaces hydrazine Schiff alkali is:
Wherein comprise-NH of R base 2,-SCH 3,-SCH 2ph ,-CH 2cH 3,-CH 2cH 2cH 3or-CH 2cH 2cH 2cH 3.
CN201410366596.7A 2014-07-29 2014-07-29 Method for preparing hydrazine Schiff alkali substituted by 1-phenyl-5-diferrocenyl-1,3-pentadiene-5-ketal Pending CN104098610A (en)

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Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1386735A (en) * 2001-05-23 2002-12-25 中国科学院化学研究所 Process for condensating salicyladehyde with arylamine
CN103880892A (en) * 2014-03-06 2014-06-25 陕西科技大学 Acyl ferrocene hydrazinodithioformate Schiff base and preparation method thereof

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