CN106800519A - Ultrasonic radiation method Fast back-projection algorithm bridging type pair, the universal method of three, four amide derivatives and application - Google Patents

Ultrasonic radiation method Fast back-projection algorithm bridging type pair, the universal method of three, four amide derivatives and application Download PDF

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CN106800519A
CN106800519A CN201710069957.5A CN201710069957A CN106800519A CN 106800519 A CN106800519 A CN 106800519A CN 201710069957 A CN201710069957 A CN 201710069957A CN 106800519 A CN106800519 A CN 106800519A
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chloride
amine
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CN106800519B (en
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陈连清
黄林伟
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South Central Minzu University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

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Abstract

The invention belongs to technical field of organic synthesis, the universal method of a kind of double bridging type, three, four amide derivatives and its ultrasonic radiation Fast back-projection algorithm is specifically disclosed, further relate to the application of such compound.The present invention prepares target product using ultrasonic radiation method, it is not added with catalyst, as long as in 30 minutes or so reaction time, reaction temperature is low, easy to operate, post processing only needs filtration washing, solvent recoverable, product yield high can effectively reduce production cost, energy-conserving and environment-protective, can be applied to large-scale industrial production.The bridging type for preparing is double, three, four amide derivatives have good bioactivity, is had a extensive future in antibacterial field, with very big development and application values.

Description

Ultrasonic radiation method Fast back-projection algorithm bridging type is double, the universal method of three, four amide derivatives And application
Technical field
The present invention relates to technical field of organic synthesis, more particularly to a kind of bridging type is double, three, four amide derivatives and its super Sonic radiation process Fast back-projection algorithm simultaneously can further relate to the application of the analog derivative with the universal method of industrialized production.
Background technology
Amides compound is important organic synthesis intermediate, is widely used in the chemical industry such as medicine, agricultural chemicals, lubricant former The production of material.In all kinds of amide compounds, bisamide, triamide and four acid amides have heterogeneity.Bisamide class compound With extensive bioactivity, can with anti-inflammatory, antibacterial, antitumor, weeding, desinsection and antiviral etc., phthalic diamides and The class compound of anthranilic diamides two, is efficient, low toxicity, the new bisamide insecticide developed in recent years；Pregnancy Base phosphoric triamide is the triamide insecticide of a class low toxicity, while being also good aprotic solvent；Four acid amides have cyclic peptide knot Structure, can be complexed with inorganic oxygen anion, form anion complex, can be used to detect environment and medical science harmful anion.
At present, the method for synthesis bisamide has, can be reacted by the direct polycondensation of carboxylic acid and amine, amine and carboxylic acid halides or The hydrolysis of the acylation reaction and nitrile of acid anhydrides and oxime are directly prepared, but are difficult to two amido links of direct construction, otherwise point multistep Reaction, or by a series for the treatment of such as activated group, making synthetic route increasingly complex, the reaction time is long, and post processing is difficult, produces Rate is not high, and maximum problem is that each method applicability is not strong, and each method is only suitable only for the compound of a certain type； The synthetic method of triamide and four acid amides it is extremely complex, it is necessary to by a series of group activation, add substantial amounts of triethylamine, The alkali such as NaOH or pyridine is used as the acid binding agent conversion simultaneously synthesizing multiple amido links of ability, will typically add catalyst auxiliary Completion is helped, it is necessary to be heated to reflux, reactions steps are more, the time is long, therefore it is considerably less to synthesize the report of this two classes compound.The above three Class compound synthesis are required to oil bath back flow reaction, because pyroreaction can produce many side reactions, cause post processing complicated, produce Thing is difficult purifying, and energy consumption is big, and the reaction time is long, while it is seriously polluted to add organic solvent to cause, is unfavorable for industrialized production, has When catalyst need to be added to cause post-reaction treatment more complicated to accelerate reaction rate, therefore it is more to find a kind of synthesis of universal method Acid amides becomes need at present the eager problem for solving.
In recent years, ultrasonic wave is introduced into " phonochemistry " risen in chemical reaction, causes people's extensive concern.Ultrasonic wave Being propagated in medium can cause the intermolecular severe friction of medium and heat to dissipate, so as to produce various secondary ultrasound wave effects：Heat Effect, chemical effect and other physical effects etc..Ultrasonic wave in organic synthesis because with reaction condition is gentle, clean energy, Easy to operate the advantages of, it has been widely used in all kinds of reactions.What ultrasonic radiation was produced to reactant is " cavitation " and secondary Level effect, can produce the TRANSIENT HIGH TEMPERATURE high pressure for being adequate to bring about chemical reaction, form local high energy center, promote reaction solution acute Strong stirring, it is comprehensive well mixed, and induce the fracture of carbon-halogen bond so that the nucleophilic attack of amine is more prone to, and reaction speed adds Hurry up, yield is increased substantially under normal temperature.It is many in bridging type although ultrasonic irradiation is widely used in organic synthesis field Acid amides synthesis aspect has not been reported.This method uses " cavitation " and second order effect of ultrasonic radiation, it is not necessary to plus it is any Catalyst, reaction need not be heated to reflux, and product is directly separated out from dichloromethane, it is to avoid complicated subsequent treatment, is located afterwards Reason is very simple；A series of bridging types pair, three, four amide derivatives can be quickly prepared under room temperature condition, the reaction time is short, instead Mild condition is answered, easy to operate, post processing is easy, solvent recoverable, and high income, is that one kind can effectively reduce production Cost, energy-conserving and environment-protective simultaneously can be with the universal method of industrialized production.
The content of the invention
Based on considerations above, applicant's design has synthesized a series of bridging types pair, three, four amide derivatives (I).In ultrasound Under " cavitation " and second order effect of radiation, many acyl chlorides of aryl or aryl-polycarboxylic acids react with amine, introduce two, three or four Individual amide groups, bridging type of the synthesis with antibacterial activity is double, three, four amide derivatives (I).Bridging type is double, three, four amide derivatives Thing has a extensive future in antibacterial field, with very big development and application values.
Based on considerations above, three goals of the invention of the invention are：
First, a kind of bridging type pair, three, four amide derivatives are provided, shown in the structural formula such as formula (I) of the analog derivative：
In formula (I), R1, R2 are each independently selected from any one in following group：H, C1-C18 alkyl, C2-C6 chains Alkenyl, C2-C6 alkynyls, C3-C8 cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyridine radicals, quinoline Quinoline base, indyl and xenyl；
Further, when R1 or R2 is C3-C8 cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thiophene During any one in base, pyridine radicals, quinolyl, indyl and xenyl, position quilt optional on each ring or ring system 1-5 each independent substitution base is replaced, replace base be each independently selected from halogen, cyano group, nitro, alkyl, alkoxy and Any one in hydroxyl；
Preferably, R1, R2 are each independently selected from any one in following group：H, C1-C18 alkyl, C2-C6 alkenes Base, C2-C6 alkynyls, C3-C8 cycloalkyl, phenyl, naphthyl, furyl, thienyl, pyridine radicals and xenyl；Work as R1Or R2For During any one in C3-C8 cycloalkyl, phenyl, naphthyl, furyl, thienyl, pyridine radicals and xenyl, each ring or Optional position is replaced by each independent substitution base of 1-5 in ring system, substituted radical be each independently selected from halogen, nitro, Any one in alkyl, alkoxy and hydroxyl；
G- groups are selected from any one in following group：C1-C12 alkyl, C2-C6 alkenyls, C2-C6 alkynyls, C2-C6 Cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyridine radicals, quinolyl, indyl, xenyl,
When G- groups are C2-C6 cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyridine Base, quinolyl, indyl, xenyl, In any one when, optional position can be replaced by each independent substitution base of 1-5 on each ring, and substituted radical is each It is independently selected from any one in halogen, nitro, alkyl, alkoxy and hydroxyl；
Preferably, G- groups are selected from any one in following group： Optional position can be by 1-5 each on each ring Independent substitution base is replaced, and substituted radical is each independently selected from any in halogen, nitro, alkyl, alkoxy and hydroxyl It is a kind of；
In above-mentioned formula (I), n is 2 or 3 or 4；
2nd, second object of the present invention is that a kind of offer reaction time is short, and reaction condition is gentle, easy to operate, after Treatment is easy, solvent recoverable, and high income, and low production cost, energy-conserving and environment-protective simultaneously can be with industrialized production bridging type The universal synthesis method of double, three, four amide derivatives (compound shown in formula (I)).
A kind of universal synthesis method of structural formula compound as shown in formula (I)：In " cavitation " of Ultrasonic Radiation Under second order effect, fast reaction is obtained amine in organic solvent with compound A；
The bridging type is double, the structural formula such as formula (I) of three, four amide derivatives is shown：
Synthetic route is as follows：
R1、R2Text as defined above is described；
Specifically, the amine is selected from any one in following compound：
Methylamine CH3NH2, ethamine CH3CH2NH2, propylamine CH3CH2CH2NH2, isopropylamine CH (CH3)2NH2, butylamine CH3CH2CH2CH2NH2, sec-butylamine CH3CH2(CH3)CHNH2, isobutyl amine CH (CH3)2CH2NH2, tert-butylamine (CH3)3NH2, amylamine CH3 (CH2)3CH2NH2, 2- amylamines CH3CH(NH2)CH2CH2CH3, 3- amylamines CH3CH2CH(NH2)CH2CH3, 1,5- dimethylhexylamines (CH3)2CH(CH2)3(CH3)CHNH2, amylamine (the CH of 4- methyl -33)2CHCH(NH2)CH2CH3, n-hexylamine CH3(CH2)4CH2NH2、 2 ethyl hexylamine CH3CH2CH(CH2NH2)(CH2)3CH3, 1- nonyl amines CH3(CH2)7CH2NH2, decyl amine CH3(CH2)8CH2NH2, bay Amine CH3(CH2)10CH2NH2, tridecyl amine CH3(CH2)11CH2NH2, tetradecy lamine CH3(CH2)12CH2NH2, cetylamine CH3(CH2)15CH2NH2, octadecylamine CH3(CH2)16CH2NH2, 2- allylamines H2C=CHCH2NH2, 2- butenylamines H3CHC=CHCH2NH2, alkynes third Amine CH ≡ CCH2NH2, 2- methyl -3- crotonylenes-amine HC ≡ CC (CH3)2CH-, cyclopropylamineRing butylamine3- methyl ring butylamineCyclopentamineCyclohexylamine4- methyl rings HexylamineCycloheptyl alkanamine2-thenylaminine2 thiophene ethyl amine2- furans Methylamine2- aminomethyl-pyridinesThe picoline of 2- amino -4AnilineO-toluidineM-toluidineOpen-chain crown ether23 dimethyl aniline2,4- dimethylanilines2,5- dimethylanilines2,6- dimethylanilines3,4- dimethylanilines3,5- Dimethylaniline2,4,6- dimethylanilinesO ethyl aniline2,6- diethylanilinesTo butylaniline4- tert-butyl group anilineO-chloranilineM-chloroanilineParachloroanilinum2,3- dichloroanilines2,4 dichloro aniline2,5- dichloroanilines2,6- dichloroanilines3,4- dichloroanilines3,5- dichloroanilinesIt is adjacent AminoanisoleM-anisidineP-nethoxyaniline2,4,6- dimethylanilinesOrtho-nitranilineParanitroanilinumParanitroanilinumNaphthalidine 2- naphthylamines1,2,3,4- tetrahydrochysene naphthalidines4- nitros-naphthalidineAnd 2- amino Biphenyl
Preferably, the amine is selected from any one in following compound：
Methylamine CH3NH2, ethamine CH3CH2NH2, propylamine CH3CH2CH2NH2, cyclopropylamine2- allylamines H2C= CHCH2NH2, propargylamine HC ≡ CCH2-, butylamine CH3CH2CH2CH2NH2, cyclopentamine2-thenylaminine 2- furylamines2- aminomethyl-pyridinesAnilineOpen-chain crown ether23 dimethyl aniline4- tert-butyl group anilineParachloroanilinumP-nethoxyanilineParanitroanilinumAnd 2- naphthalenes Amine
The compound A is selected from any one in following compound：
Oxalyl chlorideOxalic acidMalonyl chlorideMethyl malonyl chlorideDimethyl propylene diacid chlorideEthyl malonyl chlorideMalonic acidSuccinyl chlorideSuccinic acidGlutaryl chlorineGlutaric acidAdipoyl ChlorideAdipic acidIsosorbide-5-Nitrae-hexamethylene diacid chloridePimeloyl chloridePimelic acidSuberoyl chlorineSuberic acidAzelaoyl chlorideAzelaic acidSebacoyl chlorideDecanedioic acidHeneicosanedioic acidDecyl diacid chloridesDodecane DiacidO-phthaloyl chlorideM-phthaloyl chlorideParaphthaloyl chloride2,3,5,6- tetrachloro-p-phenylene's dimethyl chloridesPyromellitic trimethylsilyl chloride2, 5- furans dimethyl chlorides2,5- thiophene dimethyl chlorides2,6- pyridine dimethyl chlorides2,6- naphthalene dimethyl chloridesPhthalic acid3- nitrophthalic acids3- chloro-o-phthalic acids4- methylphthalic acids4- phthalate bromines4- fluorine phthalic acids4- hydroxyl phthalics4- nitros are adjacent Phthalic acidTetrachlorophthalic acidM-phthalic acidBetween 4- hydroxyls Phthalic acid4- bromine M-phthalic acids4- fluorine M-phthalic acids5- nitre Base M-phthalic acid5- Hydroxy M Phthalic AcidsTerephthalic acid (TPA)2- chlorine terephthalic acid (TPA)s2- bromo terephthalic acids2,5- Dihydric para-phthalic acidMethylterephthalic acidTetrafluoro terephthalic acid (TPA)NitroterephthalicL,2,3 benzene tricarboxylic acidEqual benzene Tricarboxylic acid3,3'4,4'- biphenyltetracarboxyacid acidsPyromellitic AcidAnd 1,4,5,8 naphthalenetetracarboxylic acid
Preferably, the compound A is selected from any one in following compound：
O-phthaloyl chlorideM-phthaloyl chlorideParaphthaloyl chloride Pyromellitic trimethylsilyl chloride2,5- furans dimethyl chlorides2,5- thiophene dimethyl chlorides2,6- naphthalene dimethyl chloridesPhthalic acidM-phthalic acidTerephthalic acid (TPA)Trimesic acid3,3', 4,4'- biphenyl tetracarboxylic acid AcidPyromellitic AcidAnd 1,4,5,8 naphthalenetetracarboxylic acid
As n=2, described compound (I) is bridging type bisamide derivatives, the mol ratio of amine and compound A for 2~ 2.1:1；
As n=3, described compound (I) is bridging type trigalloyl amine derivative, the mol ratio of amine and compound A for 3~ 3.1:1；
As n=4, described compound (I) is the amide derivatives of bridging type four, the mol ratio of amine and compound A for 4~ 4.1:1；
Further, as n=2, described compound (I) is bisamide derivatives, and amine is 2 with the mol ratio of compound A: 1；
As n=3, described compound (I) is trigalloyl amine derivative, and amine is 3 with the mol ratio of compound A:1；
As n=4, described compound (I) is four amide derivatives, and amine is 4 with the mol ratio of compound A:1；
The organic solvent is selected from saturation alkyl halide hydro carbons, arene or alcohols solvent.
Further, the organic solvent is selected from dichloromethane or chloroform in saturation halogenated alkanes solvents；
Or, the organic solvent is selected from the toluene in aromatic hydrocarbon solvent, dimethylbenzene or mesitylene；
Or, the organic solvent is selected from the methyl alcohol in alcohols solvent, ethanol or butanol；
Optimal, the organic solvent is dichloromethane, toluene, dimethylbenzene or ethanol.
The Ultrasonic Radiation reaction temperature is 20~60 DEG C, and the reaction time is 15~60 minutes, reactor power 100~ 200W。
Preferably, the Ultrasonic Radiation reaction temperature is 30 DEG C, and the reaction time is 30~60 minutes, reactor power 150W。
3rd, third object of the present invention there are provided a kind of above-mentioned bridging type pair, three, four amide derivatives in antibacterial The application in field.
To realize third object of the present invention, bridging type pair, three, four amide derivatives use that the present invention will be prepared Application study in anti-Escherichia coli, staphylococcus aureus and helicobacter pylori, excellent effect.
Compared with prior art, the advantages of the present invention are as follows：
The present invention quickly prepares bridging type pair, three, four amide derivatives (I) using ultrasonic radiation method, and ultrasonic radiation is to anti- " cavitation " and second order effect for answering thing to produce, generation are adequate to bring about the TRANSIENT HIGH TEMPERATURE high pressure of chemical reaction, form part High energy center, promotes reaction solution to be stirred vigorously, comprehensive mixing, and induces the fracture of carbon-halogen bond so that the nucleophilic attack of amine is more Plus easily, reaction speed is accelerated, yield is increased substantially, and makes the universal method of synthesis different type acid amides.Using this Method prepares bridging type pair, three, four amide derivatives (I), it is not necessary to by a series of group activation, need not design function Group's conversion, is added without the alkali such as substantial amounts of triethylamine, NaOH or pyridine as acid binding agent, one-step method direct construction multiple acid amides Key, reaction does not need condensing reflux, product is directly separated out from dichloromethane, it is to avoid complicated subsequent treatment, post-processes non- It is often simple；Can be reacted under room temperature condition, the reaction time is short, easy to operate, post processing is easy, solvent recoverable, and receives Rate is high, is that one kind can effectively reduce production cost, and energy-conserving and environment-protective simultaneously can be in the method for industrialized production.
The bridging type for preparing is double, three, four amide derivatives (I) with good bioactivity, in antibiosis table Reveal high activity, with very big development and application values.
Specific embodiment
With reference to specific embodiment, the present invention is described in further detail, but these specific embodiments are not with any Mode is limited the scope of the invention.
Raw material used is known compound in following embodiment, is commercially available, or can be with this area The method synthesis known.
Embodiment 1, N1,N4The synthesis of-dipropyl terephthalamide ((I) 1)
0.60g propylamine is weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, round bottom flask is entered into ultrasonic wave In reactor, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, to dropwise addition 10mL in reaction solution dissolved with 1.02g The dichloromethane solution of paraphthaloyl chloride.Suction filtration after reaction 25min, 3 washings are divided with 5mL10wt% sodium hydroxide solutions, Obtain white solid 0.99g, yield 86%, mp:186.4~187.3 DEG C of .IR ν (cm-1):3220(N-H),3048(C-H),1711 (- C=O), 1564 and 1433 (phenyl ring skeletal vibrations), 881 (aromatic ring C-H)1H NMR(DMSO,400MHz):8.44(s,2H, N-H),8.22(s,4H,Ar-H),3.44(s,4H,C-H),3.23(s,4H,C-H),2.32(t,6H,C-H).
Embodiment 2, N1,N4The synthesis of-dipropargyl terephthalamide ((I) 2)
0.58g propargylamines are weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, round bottom flask is entered into ultrasound In ripple reactor, set radiant power 150W, 30 DEG C of reaction temperature, open reactor, in reaction solution be added dropwise 10mL dissolved with The dichloromethane solution of 1.03g paraphthaloyl chlorides.Suction filtration after reaction 35min, is divided 3 times with 5mL10wt% sodium hydroxide solutions Washing, obtains white solid 0.98g, yield 82%, mp:200.4~200.6 DEG C of .IR ν (cm-1):3228(N-H),3045(C-H), 1718 (- C=O), 1569 and 1447 (phenyl ring skeletal vibration), 886 (aromatic ring C-H)1H NMR(DMSO,400MHz):8.72(s, 2H,N-H),8.29(s,4H,Ar-H),3.10(s,2H,C-H),2.00(s,2H,C-H).
Embodiment 3, N1,N3The synthesis of-diphenyl isophtalamide ((I) 3)
0.56g aniline is weighed in 100mL round-bottomed flasks, 50mL ethanol is added, round bottom flask is entered into ultrasonic response In device, radiant power 150W is set, 35 DEG C of reaction temperature opens reactor, to dropwise addition 10mL in reaction solution dissolved with 1.02g isophthalic The ethanol solution of dimethyl chloride.Suction filtration after reaction 30min, with 3 washings of 5mL10wt% sodium hydroxide solutions point, obtains white solid Body 1.42g, yield 90%, mp:230.6~230.9 DEG C of .IR ν (cm-1):3224 (N-H), 3056 (C-H), 1722 (- C=O), 1529 and 1407 (phenyl ring skeletal vibrations), 883 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.02(s,2H,N-H), 8.29(s,1H,Ar-H),8.14(d,4H,Ar-H),7.74(t,5H,Ar-H),7.33(t,2H,Ar-H),7.23(t,2H,Ar- H).
Embodiment 4, N2,N5The synthesis of-diphenyl furans diformamide ((I) 4)
0.60g aniline is weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, round bottom flask is entered into ultrasonic wave In reactor, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, to dropwise addition 10mL in reaction solution dissolved with 0.98g The dichloromethane solution of 2,5- dimethyl chloride furans.Suction filtration after reaction 45min, is divided 3 times with 5mL10wt% sodium hydroxide solutions and washed Wash, obtain white solid 1.36g, yield 89%, mp:167.15~168.43 DEG C of .IR ν (cm-1):3222(N-H),3024(C-H), 1711 (- C=O), 1525 and 1423 (phenyl ring skeletal vibration), 801 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.22 (s,2H,N-H),8.29(s,1H,Ar-H),8.12(d,4H,Ar-H).
Embodiment 5, N2,N6The synthesis of-two p-fluorophenyl aphthalimides ((I) 5)
1.12g para-fluoroaniline is weighed in 100mL round-bottomed flasks, 50mL toluene is added, round bottom flask is entered into ultrasonic wave In reactor, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, to dropwise addition 10mL in reaction solution dissolved with 1.26g The toluene solution of 2,6- naphthalene dimethyl chlorides.Suction filtration after reaction 35min, with 3 washings of 5mL10wt% sodium hydroxide solutions point, obtains White solid 1.53g, yield 76%, mp:187.15~188.3 DEG C of .IR ν (cm-1):3102(N-H),3024(C-H),1709(- ), C=O 1525 and 1423 (phenyl ring skeletal vibration) 1339 (C-F), 811 (aromatic ring C-H)1H NMR(DMSO,400MHz): 10.22(s,2H,N-H),8.29(s,1H,Ar-H),8.11(d,4H,Ar-H),7.79(d,2H,Ar-H),7.29(s,1H,Ar- H).
Embodiment 6, N1,N2The synthesis of-di-p-tolyl phthalic amide ((I) 6)
1.10g para-totuidine is weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, by the round bottom flask excess of imports In sound wave reactor, set radiant power 150W, 30 DEG C of reaction temperature, open reactor, in reaction solution be added dropwise 10mL dissolved with The dichloromethane solution of 0.83g phthalic acids.Suction filtration after reaction 15min, is divided 3 times with 5mL10wt% sodium hydroxide solutions and washed Wash, obtain white solid 1.43g, yield 83%, mp:165.5~166.3 DEG C of .IR ν (cm-1):3202(N-H),3034(C-H), 1699 (- C=O), 1525 and 1443 (phenyl ring skeletal vibration), 823 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.17 (s,2H,N-H),8.29(s,1H,Ar-H),8.11(d,4H,Ar-H),7.75(d,2H,Ar-H),7.26(s,1H,Ar-H), 7.11(t,3H,Ar-H).
Embodiment 7, N1,N3,N5The synthesis of the equal benzene trimethamide of-three normal-butyls ((I) 7)
0.73g n-butylamines are weighed in 100mL round-bottomed flasks, 50mL ethanol is added, round bottom flask is entered into ultrasonic wave anti- Answer in device, radiant power 150W is set, 35 DEG C of reaction temperature opens reactor, and 10mL is equal dissolved with 1.10g to being added dropwise in reaction solution The ethanol solution of benzenetricarboxylic acid.Suction filtration after reaction 30min, with 3 washings of 5mL10wt% sodium hydroxide solutions point, obtains white solid Body 1.55g, yield 86%, mp:165.5~166.3 DEG C of .IR ν (cm-1):3202 (N-H), 3034 (C-H), 1699 (- C=O), 1525 and 1443 (phenyl ring skeletal vibrations), 823 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.17(s,2H,N-H), 8.29(s,1H,Ar-H),8.18(d,4H,Ar-H),7.69(d,2H,Ar-H),7.12(s,1H,Ar-H),7.11(t,3H,Ar- H).
Embodiment 8, N1,N3,N5The synthesis of the equal benzene trimethamide of-three propargyls ((I) 8)
0.68g propargylamines are weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, round bottom flask is entered into ultrasound In ripple reactor, set radiant power 150W, 30 DEG C of reaction temperature, open reactor, in reaction solution be added dropwise 10mL dissolved with The dichloromethane solution of 1.10g trimesic acids.Suction filtration after reaction 25min, is divided 3 times with 5mL10wt% sodium hydroxide solutions and washed Wash, obtain white solid 1.22g, yield 76%, mp:195.5~196.3 DEG C of .IR ν (cm-1):3244(N-H),3024(C-H), 1739 (- C=O), 1525 and 1443 (phenyl ring skeletal vibration), 801 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.02 (s,3H,N-H),8.29(d,3H,Ar-H),4.29(t,6H,C-H),2.11(d,3H,Ar-H).
Embodiment 9, N1,N3,N5The synthesis of the equal benzene trimethamide of-triphenyl ((I) 9)
1.40g aniline is weighed in 100mL round-bottomed flasks, 50mL dimethylbenzene is added, round bottom flask is entered into ultrasonic wave anti- Answer in device, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, and 10mL is equal dissolved with 1.31g to being added dropwise in reaction solution The xylene solution of the formyl chloride of benzene three.Suction filtration after reaction 35min, with 3 washings of 5mL10wt% sodium hydroxide solutions point, obtains white Color solid 1.80g, yield 83%, mp:244.5~245.3 DEG C of .IR ν (cm-1):3143 (N-H), 3042 (C-H), 1744 (- C= ), O 1565 and 1483 (phenyl ring skeletal vibration), 801 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.09(d,3H,N-H), 8.29(d,3H,Ar-H),8.11(t,6H,C-H),8.02(t,4H,C-H),7.08(s,2H,C-H),6.90(d,3H,C-H).
Embodiment 10, N1,N3,N5The synthesis of the equal benzene trimethamide of-three thienyls ((I) 10)
1.50g 2- aminothiophenes are weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, round-bottomed flask is put into In ultrasound reactor, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, and 10mL is molten to being added dropwise in reaction solution There is the dichloromethane solution of 1.30g pyromellitic trimethylsilyl chlorides.Suction filtration after reaction 30min, with 5mL10wt% sodium hydroxide solutions point 3 Secondary washing, obtains faint yellow solid 2.06g, yield 91%, mp:224.5~225.3 DEG C of .IR ν (cm-1):3153(N-H),3022 (C-H), 1714 (- C=O), 1565 and 1483 (phenyl ring skeletal vibration), 816 (aromatic ring C-H)1H NMR(DMSO,400MHz): 10.09(d,3H,N-H),8.29(d,3H,Ar-H),8.11(t,6H,C-H),8.02(t,4H,C-H),7.08(s,2H,C-H), 6.90(d,4H,C-H).
Embodiment 11, N1,N2,N4,N5The synthesis of the formamide of-Fourth Ring amylbenzene four ((I) 11)
1.70g cyclopenta amine is weighed in 100mL round-bottomed flasks, 50mL ethanol is added, round bottom flask is entered into ultrasonic wave In reactor, set radiant power 150W, 30 DEG C of reaction temperature, open reactor, in reaction solution be added dropwise 10mL dissolved with The ethanol solution of 1.27g1,2,4,5- benzene tetracarboxylic acids.Suction filtration after reaction 30min, is divided 3 times with 5mL10wt% sodium hydroxide solutions Washing, obtains yellow solid 1.98g, yield 76%, mp:254.6~255.2 DEG C of .IR ν (cm-1):3133(N-H),3032(C-H), 1744 (- C=O), 1568 and 1491 (phenyl ring skeletal vibration), 810 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.09 (d,4H,N-H),8.29(d,3H,Ar-H),7.29(s,3H,C-H).
Embodiment 12, N2,N3,N6,N7The synthesis of the formamide of-tetraphenyl naphthalene four ((I) 12)
0.56g aniline is weighed in 100mL round-bottomed flasks, 50mL dichloromethane is added, round bottom flask is entered into ultrasonic wave In reactor, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, to dropwise addition 10mL in reaction solution dissolved with 1.52g The dichloromethane solution of 2,3,6,7- naphthalenetetracarbacidic acidics.Suction filtration after reaction 60min, is divided 3 times with 5mL10wt% sodium hydroxide solutions and washed Wash, obtain yellow-brown solid 2.90g, yield 96%, mp:264.1~265.9 DEG C of .IR ν (cm-1):3123(N-H),3022(C-H), 1754 (- C=O), 1578 and 1511 (phenyl ring skeletal vibration), 815 (aromatic ring C-H)1H NMR(DMSO,400MHz):10.09 (d,4H,N-H),8.29(d,4H,Ar-H),8.29(d,4H,Ar-H),8.29(s,4H,Ar-H),8.29(t,4H,Ar-H).
Embodiment 13, N3,N3',N4,N4The synthesis of the formamide of '-tetraphenyl naphthalene four ((I) 13)
0.56g propylamine is weighed in 100mL round-bottomed flasks, 50mL dimethylbenzene is added, round bottom flask is entered into ultrasonic wave anti- Answer in device, radiant power 150W is set, 30 DEG C of reaction temperature opens reactor, to dropwise addition 10mL in reaction solution dissolved with 1.55g The xylene solution of 3,3', 4,4'- biphenyltetracarboxyacid acid.Suction filtration after reaction 45min, is divided 3 times with 5mL10wt% sodium hydroxide solutions Washing, obtains pale solid 2.00g, yield 81%, mp:264.1~265.9 DEG C of .IR ν (cm-1):3143(N-H),3112(C- ), H 1746 (- C=O), 1534 and 1498 (phenyl ring skeletal vibration), 803 (aromatic ring C-H)1H NMR(DMSO,400MHz): 10.09(d,4H,N-H),8.29(t,6H,Ar-H),4.33(s,2H,C-H),4.29(s,4H,C-H),4.11(s,2H,C-H).
Comparative example, N1,N4- diphenyl isophtalamide and N1,N3,N5The synthesis of the equal benzene trimethamide of-triphenyl
Separately or concurrently change reaction temperature, reaction time, reactive mode and the raw material dosage (amine/acyl of embodiment 3 Chlorine), solvent is changed to dichloromethane, and other are same as Example 3, prepares N1,N4- diphenyl isophtalamide, prepare result with The result of embodiment 3 is while in being listed in the table below 1 (comparative example 1-8)；Increase N1,N3,N5The synthesis of the equal benzene trimethamide of-triphenyl (comparative example 9-10, with embodiment 9, solvent is changed to dichloromethane to reactant), (solvent is dichloromethane to the versatility of observation procedure Alkane)：
The synthesis of embodiment 3 and its yield under the conditions of the differential responses of table 1.
Can be seen that reaction temperature by comparative example 1-10 influences yield with the reaction time, keeps rate of charge constant, changes Reaction temperature and reaction time, using ultrasonic radiation method compared with oil bath, yield is substantially improved, and reacts optimum reaction condition For：30 DEG C, reaction time 30min；Change rate of charge, keep most suitable reaction temperature constant with the reaction time, it can be seen that In high-volume course of reaction (comparative example 5-8), ultrasonic radiation method remains unchanged higher than oil bath yield, and ultrasonic radiation method yield is quite managed Think, be adapted to industrialized production.Oil bath reflow method yield can be seen that by comparative example 9-10 very low, be not suitable for N1,N3,N5- three The synthesis of the equal benzene trimethamide of phenyl, but 76% can be improved yields into using ultrasonic radiation method, illustrate that ultrasonic radiation method is Synthesize the universal method of the analog derivative thing.
The preparation of many antimicrobials of base acid amides (I) 1~13 of embodiment 14, bridging type
Antibacterial formulation manufactured in the present embodiment is solution, totally 13 kinds of test compound difference prepared by embodiment 1-13 It is dissolved in DMSO, the solution that concentration is 0.1% (g/mL) is made into advance, is then diluted to 1wt% aqueous acetic acids respectively , used as test sample, Norfloxacin (NF) is used as positive for 4 gradient concentrations of 12.5mg/L, 2.5mg/L, 0.5mg/L, 0.1mg/L Comparison medicine, 4 gradient concentrations of 12.5mg/L, 2.5mg/L, 0.5mg/L, 0.1mg/L are configured to 1wt% aqueous acetic acids, are made It is isoconcentration blank control group.
Each dilute solution agent prepared by above is ready for use on following embodiment.
Embodiment 15, the antibacterial activity evaluation to staphylococcus aureus
Antibacterial activity evaluation to staphylococcus aureus uses plate test method determination, is prepared using embodiment 1~13 Each compound dilute solution agent, using tryptone as culture medium, inoculation cultivates 24h after 37 DEG C, observes, records antibacterial Circle size, and compared with positive control drug Norfloxacin (NF), the bacteriostatic activity of test compound is evaluated according to this just, ++ represent High activity ,+medium activity is represented ,-represent that activity is weaker.The results are shown in Table 2.
The anti-Staphylococcus aureus activity of the compound of table 2. ((I) 1~13)
Embodiment 16, the antibacterial activity evaluation to Escherichia coli
Antibacterial activity evaluation to Escherichia coli uses plate test method determination, eachization prepared using embodiment 1~13 The dilute solution agent of compound, using tryptone as culture medium, 24h is cultivated in inoculation after 37 DEG C, and observation, record inhibition zone are big It is small, and compared with positive control drug Norfloxacin (NF), the bacteriostatic activity of test compound is evaluated according to this just, ++ represent high living Property ,+medium activity is represented ,-represent that activity is weaker.The results are shown in Table 3.
The anti-E. coli Activity of the compound of table 3. (I1~13)
Embodiment 17, the antibacterial activity evaluation to helicobacter pylori
Antibacterial activity evaluation to helicobacter pylori uses plate test method determination, uses each of the preparation of embodiment 1~13 The dilute solution agent of compound, using tryptone as culture medium, 24h is cultivated in inoculation after 37 DEG C, and observation, record inhibition zone are big It is small, and compared with positive control drug Norfloxacin (NF), the bacteriostatic activity of test compound is evaluated according to this just, ++ represent high living Property ,+medium activity is represented ,-represent that activity is weaker.The results are shown in Table 3.
The helicobactor pylori activity of the compound of table 3. (I1~13)

Claims (11)

1. a kind of bridging type is double, three, four amide derivatives, and its structural formula is as led to shown in formula (I)：
R1、R2It is each independently selected from any one in following group：H, C1-C18 alkyl, C2-C6 alkenyls, C2-C6 alkynyls, C3-C8 cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyridine radicals, quinolyl, indyl and Xenyl；
Further, when R1 or R2 is C3-C8 cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyrrole During any one in piperidinyl, quinolyl, indyl and xenyl, optional position is by 1-5 on each ring or ring system Each independent substitution base is replaced, and substituted radical is each independently selected from halogen, cyano group, nitro, alkyl, alkoxy and hydroxyl In any one；
N is 2 or 3 or 4；
G- groups are selected from any one in following group：C1-C18 alkyl, C2-C6 alkenyls, C2-C6 alkynyls, C2-C6 cycloalkanes Base, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyridine radicals, quinolyl, indyl, xenyl, two take For phenyl, tri-substituted phenyl, tetra-substituted phenyl,
Further, when G- groups are C2-C6 cycloalkyl, phenyl, naphthyl, anthryl, phenanthryl, furyl, pyrrole radicals, thienyl, pyridine radicals, quinoline Quinoline base, indyl, xenyl, di-substituted-phenyl, tri-substituted phenyl, tetra-substituted phenyl, In any one when, optional position can be replaced by each independent substitution base of 1-5 on each ring, and substituted radical is each It is independently selected from halogen, nitro, alkyl, alkoxy, hydroxyl.
2. bridging type according to claim 1 is double, three, four amide derivatives, it is characterised in that：The R1、R2It is each independent Selected from any one in following group：H, C1-C18 alkyl, C2-C6 alkenyls, C2-C6 alkynyls, C3-C8 cycloalkyl, phenyl, Naphthyl, furyl, thienyl, pyridine radicals and xenyl；Work as R1Or R2It is C3-C8 cycloalkyl, phenyl, naphthyl, furyl, thiophene During any one in fen base, pyridine radicals and xenyl, optional position is each independent by 1-5 on each ring or ring system Substitution base replaced, substituted radical is each independently selected from any one in halogen, nitro, alkyl, alkoxy and hydroxyl.
3. bridging type according to claim 1 is double, three, four amide derivatives, it is characterised in that：The G- groups are selected from such as Any one in lower group：
4. any described bridging type is double in a kind of claim 1-3, the universal synthesis method of three, four amide derivatives：By amine Synthesized by ultrasonic radiation method in organic solvent with compound A and obtained, synthetic route is：
The amine is selected from any one in following compound：
Methylamine, ethamine, propylamine, isopropylamine, butylamine, sec-butylamine, isobutyl amine, tert-butylamine, amylamine, 2- amylamines, 3- amylamines, 1,5- bis- Tuaminoheptane, the amylamine of 4- methyl -3, n-hexylamine, 2 ethyl hexylamine, 1- nonyl amines, decyl amine, lauryl amine, tridecyl amine, tetradecy lamine, 16 Amine, octadecylamine, 2- allylamines, 2- butenylamines, propargylamine, 2- methyl -3- crotonylenes-amine, cyclopropylamine, ring butylamine, 3- methyl rings Butylamine, cyclopentamine, cyclohexylamine, 4- methyl cyclohexylamines, cycloheptyl alkanamine, 2-thenylaminine, 2 thiophene ethyl amine, 2- furylamines, 2- Aminomethyl-pyridine, the picoline of 2- amino -4, aniline, o-toluidine, m-toluidine, open-chain crown ether, 2,3- dimethyl Aniline, 2,4- dimethylanilines, 2,5- dimethylanilines, 2,6- dimethylanilines, 3,4- dimethylanilines, 3,5- dimethyl benzenes Amine, 2,4,6- dimethylanilines, o ethyl aniline, 2,6- diethylanilines, to butylaniline, 4- tert-butyl groups aniline, adjacent chlorobenzene Amine m-chloroaniline, parachloroanilinum, 2,3- dichloroanilines, 2,4 dichloro aniline, 2,5- dichloroanilines, 2,6- dichloroanilines, 3,4- Dichloroaniline, 3,5- dichloroanilines, o-aminoanisole, m-anisidine, P-nethoxyaniline, 2,4,6- dimethyl benzenes Amine, ortho-nitraniline, paranitroanilinum, paranitroanilinum, naphthalidine, 2- naphthylamines, 1,2,3,4- tetrahydrochysenes naphthalidine, 4- nitros- Naphthalidine and 2- aminobphenyls；
The compound A is selected from any one in following compound：
Oxalyl chloride, oxalic acid, malonyl chloride, methyl malonyl chloride, dimethyl propylene diacid chloride, ethyl malonyl chloride, malonic acid, fourth two It is acyl chlorides, succinic acid, glutaryl chlorine, glutaric acid, Adipoyl Chloride, adipic acid, Isosorbide-5-Nitrae-hexamethylene diacid chloride, pimeloyl chloride, pimelic acid, pungent Diacid chloride, suberic acid, azelaoyl chloride, azelaic acid, sebacoyl chloride, decanedioic acid, heneicosanedioic acid, decyl diacid chlorides, dodecane Diacid, o-phthaloyl chloride, m-phthaloyl chloride, paraphthaloyl chloride, 2,3,5,6- tetrachloro-p-phenylenes dimethyl chloride, equal benzene front three Acyl chlorides, 2,5- furans dimethyl chloride, 2,5- thiophene dimethyl chloride, 2,6- pyridines dimethyl chloride, 2,6- naphthalenes dimethyl chloride, adjacent benzene two Formic acid, 3- nitrophthalic acids, 3- chloro-o-phthalic acids, 4- methylphthalic acids, 4- phthalate bromines, 4- fluorine neighbour's benzene Dioctyl phthalate, 4- hydroxyl phthalics, 4- nitrophthalic acids, tetrachlorophthalic acid, M-phthalic acid, 4- hydroxyl isophthalic Dioctyl phthalate, 4- bromines M-phthalic acid, 4- fluorine M-phthalic acid, 5- nitroisophthalic acids, 5- Hydroxy M Phthalic Acids, to benzene two Formic acid, 2- chlorine terephthalic acid (TPA), 2- bromo terephthalic acids, 2,5- dihydric para-phthalic acids, methylterephthalic acid, tetrafluoro pair Phthalic acid, nitroterephthalic, l,2,3 benzene tricarboxylic acid, trimesic acid, 3,3'4,4'- biphenyltetracarboxyacid acids, equal benzene four Formic acid and 1,4,5,8 naphthalenetetracarboxylic acid.
5. universal synthesis method according to claim 4, it is characterised in that the amine is selected from any in following compound It is a kind of：
Methylamine, ethamine, propylamine, cyclopropylamine, 2- allylamines, propargylamine, butylamine, cyclopentamine, 2-thenylaminine, 2- furylamines, 2- aminomethyl-pyridines aniline, open-chain crown ether, 23 dimethyl aniline, 4- tert-butyl groups aniline, parachloroanilinum, to methoxybenzene Amine, paranitroanilinum and 2- naphthylamines.
6. universal synthesis method according to claim 4, it is characterised in that：The compound A is selected from following compound Any one：
O-phthaloyl chloride, m-phthaloyl chloride, paraphthaloyl chloride, pyromellitic trimethylsilyl chloride, 2,5- furans dimethyl chloride, 2,5- Thiophene dimethyl chloride, 2,6- naphthalenes dimethyl chloride, phthalic acid, M-phthalic acid, terephthalic acid (TPA), trimesic acid, 3,3', 4,4'- biphenyltetracarboxyacid acids, Pyromellitic Acid and 1,4,5,8 naphthalenetetracarboxylic acid.
7. according to any described universal synthesis method in claim 4-6, it is characterised in that：The organic solvent is selected from saturation Alkyl halide hydro carbons, arene or alcohols solvent.
8. universal synthesis method according to claim 7, it is characterised in that：The organic solvent is selected from saturation halogenated alkane Dichloromethane or chloroform in class solvent；
Or, the organic solvent is selected from the toluene in aromatic hydrocarbon solvent, dimethylbenzene or mesitylene；
Or, the organic solvent is selected from the methyl alcohol in alcohols solvent, ethanol or butanol.
9. universal synthesis method according to claim 8, it is characterised in that：The organic solvent be dichloromethane, toluene, Dimethylbenzene or ethanol.
10. synthetic method according to claim 9, it is characterised in that：The ultrasonic radiation method reaction temperature is 20~60 DEG C, the reaction time is 15~60 minutes.
11. universal synthesis methods according to claim 4, it is characterised in that：As n=2, described compound (I) is Bridging type bisamide derivatives, amine is 2~2.1 with the mol ratio of compound A:1；
As n=3, described compound (I) is bridging type trigalloyl amine derivative, and amine is 3~3.1 with the mol ratio of compound A: 1；
As n=4, described compound (I) is the amide derivatives of bridging type four, and amine is 4~4.1 with the mol ratio of compound A: 1。
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