CN103864702B - A kind of in water microwave catalysis prepare the method for Quinazolinone compounds - Google Patents
A kind of in water microwave catalysis prepare the method for Quinazolinone compounds Download PDFInfo
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- CN103864702B CN103864702B CN201410068513.6A CN201410068513A CN103864702B CN 103864702 B CN103864702 B CN 103864702B CN 201410068513 A CN201410068513 A CN 201410068513A CN 103864702 B CN103864702 B CN 103864702B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
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Abstract
The invention discloses<b>A kind of in water microwave catalysis prepare the method for Quinazolinone compounds</b>, utilize water-soluble complex (as: copper 8-quinolinolate) as catalyst, pure water mutually in by the reaction of microwave efficient catalytic 2-halogen benzoic acid and amidine salt, invent a kind of environmental friendliness, easy and simple to handle, safety is cheap, prepares efficiently the method for Quinazolinone compounds. Compared with prior art, the method not only can be suitable for a large amount of functional groups, and productive rate is high, and accessory substance is few, and simple to operate, and safety is with low cost, environmental protection.<b></b>
Description
Technical field
The invention discloses the method for synthetic Quinzolone derivatives. Adopting 2-halogen benzoic acid and amidine salt is that raw material is with nothingMachine mantoquita is catalyst, and in water, the method for Quinazolinone compounds is prepared in microwave catalysis reaction.
Background technology
Quinazolone is the nitrogen-containing heterocycle compound that a class has good biological medicinal activity, because it has biological widelyAnd pharmaceutically active, cause that scientists greatly studies interest. Research in recent years shows, the multi-biological of Quinazolinone compoundsActivity, is mainly manifested in EGF-R ELISA (EGFR) or its TYR kinases (EGFR-TK), vascular endothelial growth factorSub-acceptor (VEGFR), platelet derived growth factor receptor (PDGFR), trk C (NGFR) and other are multipleThe inhibition activity of action target spot, thus bring into play the multiple pharmacologically actives such as anticancer, antibacterial, antiviral. The natural biological that some are importantAlkali also contains quinazolone class skeleton, as has the orixine of anti-malarial effect. Quinazolone or fine chemistry industry and medicine are producedImportant intermediate, if the 4-amido quinazoline being obtained after chlorination, ammonification by quinazolone is that a series of medicines are as Gefitinib(Gefitinib), the basic framework of Tarceva (Erlotinib). Therefore, the new method of synthetic quinazolone is subject to extensively alwaysPay close attention to.
According to raw materials used difference, the synthetic method of current common quinazolone mainly contains: (1) taking ortho-aminobenzoic acid asRaw material (referring to: (a) M.Endicott, E.Wick, M.L.Mercury, J.Am.Chem.Soc., 1946,68,1299;(b)G.Liu,D.Y.Hu,L.H.Jin,Bioorg.Med.Chem.,2007,15,6608.); (2) taking anthranilamide as raw material (referring to (a) R.J.abdel-Jalil, W.Volter, M.Saeed,Tetrahed.Lett.,2004,45,3475;(b)M.M.Heravi,S.Sadjadi,N.M.Haj, Tetrahed.Lett., 2009,50,943.); (3) taking ortho-nitrophenyl formamide as raw material (referring to P.Mangeney, T.Tejere, A.Alexakis, Synthesis, 1988,255). These methods more or less due toRaw material obtains difficulty, the murder by poisoning of part reagent is large, reaction condition is violent and need the problems such as special reaction container, uses and is limitSystem.
It was the new problem growing up for nearly 10 years that microwave technology is applied to organic synthesis, since Gedye head in 1986Inferior delivering is applied to microwave technology after the paper of organic synthesis, and the application of microwave technology in organic synthesis is increasingly wideGeneral, compared with prior synthesizing method, microwave assisted synthesizing method has that the reaction time is short, energy-conservation, productive rate is high and environmental friendlinessEtc. advantage. In pure water phase system, prepare a method that replaces benzothiazole compound so far by microwave catalysis inorganic sulphideRarely has report. Water is widely distributed on earth, and organic solvent, cheap and easy to get relatively, and aqueous phase reactions product is simple, productive rateHigh, selectively good, easily separated purifying, pollute less and nontoxic, meet the idea of Green Chemistry and sustainable development, simple to operate,Safety, does not have the problem such as inflammable and explosive of organic solvent, aspect organic synthesis, can omit such as the protection of functional group and goThe synthesis steps such as protection (referring to: (a) U.M.Lindstrom, Chem.Rev.2002,102,2751; (b) S.Kobayahi,K.Manabe,Acc.Chem.Res.2002,35,209;(c)M.Poliakoff,J.M.Fitzpatrick,T.R.Farren,P.T.Anastas,Science2002,297,807;(d)C.-J.Li,Chem.Rev.2005,105,3095;(i)S.Minakata,M.Komatsu,Chem.Rev.2009,109,711.）。
The invention discloses the method for synthetic Quinzolone derivatives. Adopting 2-halogen benzoic acid and amidine salt is raw material, withInorganic mantoquita is catalyst, and in water, the method for Quinazolinone compounds is prepared in microwave catalysis reaction. Described in prior artMethod is compared, and this system not only can be suitable for a large amount of functional groups, and productive rate is high, and accessory substance is few, and simple to operate, and safety becomesThis is cheap, environmental protection.
Summary of the invention
The object of this invention is to provide a kind of in water microwave catalysis prepare the method for Quinazolinone compounds, in more detailSay pure water mutually in the method for the synthetic Quinazolinone compounds of water-soluble catalyst catalysis 2-halogen benzoic acid and amidine salt.
Realize technical scheme of the present invention as follows: one of the present invention microwave catalysis in water is prepared quinazoloneThe method of compound, as chemical equation (B), its concrete steps are as follows: in reaction vessel, add catalytic amount water-soluble catalystAnd 2-halogen benzoic acid substrate (B), amidine salt, inorganic base and water, be placed in microwave reactor and react, after certain hour, coolingTo room temperature, be extracted with ethyl acetate out product, reduced pressure concentration, product is through column chromatography purification; Described technical scheme is reactionSubstrate 2-halogen benzoic acid and amidine salt are raw material, under the effect of catalyst, react and form, and reaction equation is as follows:
Wherein R1Be selected from halogen atom, hydroxyl, C1-7Low alkyl group, phenyl, aralkyl, C1-4Lower alkoxy, nothing replaceOr have the phenoxy group of replacement, without replacing or having aralkoxy, pyridine radicals, Phenoxymethyl, acetyl group, nitro or the cyano group of replacement;R1Substituting group is preferably placed at the ortho position of halogen X, and a position and contraposition, more preferably in contraposition; R2For F, Cl, Br, I.
Described catalyst (B) be a kind of water-soluble transition metal complex (as: copper 8-quinolinolate) (B), be preferablyOxine copper complex. Following formula is shown in by catalyst (B):
(B)
Wherein M can be the transition metal such as iron, cobalt, nickel, manganese, copper, platinum, palladium, preferably palladium, copper, iron, more preferably copper.
According to the present invention, substrate (I) is 2-halogen benzoic acid, can in this aqueous phase reactions system, synthesize quinazolone derivativeThing.
(I)。
R in above formula (I)1For F, Cl, Br, I; Hydroxyl, C1-7Low alkyl group, phenyl, aromatic hydrocarbons, aralkyl, C1-4Rudimentary alcoxylBase, nothing replace or also can have the phenoxy group of replacement, aralkoxy, pyridine radicals, the benzene oxygen first that nothing replaces or also can have replacementBase, acetyl group, nitro, cyano group.
X is halogen atom Cl, Br, I.
According to the present invention, be amidine salt as shown in the formula (II):
（II）
Wherein R2For F, Cl, Br, I, hydroxyl, C1-7Low alkyl group, phenyl, aromatic hydrocarbons, aralkyl, pyridine radicals, Phenoxymethyl,Acetyl group, nitro, cyano group.
Products therefrom (III), wherein R1For halogen atom, hydroxyl, C1-7Low alkyl group, phenyl, aralkyl, C1-4RudimentaryAlkoxyl, nothing replace or also can have the phenoxy group of replacement, aralkoxy, pyridine radicals, the benzene that nothing replaces or also can have replacementOxygen methyl, acetyl group, nitro, cyano group.
R2For F, Cl, Br, I, hydroxyl, C1-7Low alkyl group, phenyl, aromatic hydrocarbons, aralkyl, pyridine radicals, Phenoxymethyl, acetylBase, nitro, cyano group.
（III）
In preferred version of the present invention, the consumption that it is characterized in that concrete steps amidine salt is substrate (2-halogen benzoic acid)The 1-30 of mole doubly.
Reaction system is implemented under inorganic base or organic base existence, preferably inorganic base. Inorganic base can be potassium hydroxide, hydrogen-oxygenChange lithium, NaOH, cesium carbonate, potassium fluoride, potash, sodium carbonate, potassium phosphate, sodium acid carbonate, dipotassium hydrogen phosphate, bicarbonatePotassium, sodium acetate, potassium acetate, sodium butyrate, sodium methoxide, caustic alcohol, sodium tert-butoxide, potassium tert-butoxide, trimethylacetic acid sodium, organic base can be threeEthamine, tripropyl amine (TPA), tri-n-butylamine, diisopropylethylamine. Preferably use NaOH, cesium carbonate, sodium carbonate, potassium hydroxide, phosphoric acidPotassium.
Be standard based on 1 mole of 2-halogen benzoic acid (I), the consumption of described alkali is 0.5 to 8 mole, is preferably 0.5 to 6Mole, more preferably 0.5 to 5 mole.
In preferred version of the present invention, be standard based on 1 mole of 2-halogen benzoic acid (I), the use amount of catalyst is0.01 mole to 0.5 mole, preferably 0.02 mole to 0.4 mole, more preferably 0.05 to 0.3 mole.
In preferred version of the present invention, metal in catalyst (M) can be the transition gold such as iron, cobalt, nickel, manganese, copper, platinum, palladiumBelong to, preferably palladium, copper, iron, more preferably copper.
In preferred version of the present invention, preferred quinolines of organic matter etc. in catalyst, more preferably 8-hydroxylQuinoline.
Consumption as the water of solvent can change in wide scope. The concentration of reaction substrate (2-halogen benzoic acid) is preferredBe 0.1 to 0.9mol/L, more preferably 0.3 to 0.4mol/L.
Reaction temperature in microwave reactor is 20 to 160 DEG C, preferably 20 to 150 DEG C, and more preferably 20 to 130DEG C condition under implement.
Reaction time in microwave reactor is 1-300 minute, preferably 5-160 minute.
Microwave irradiation power in microwave reactor is 20-500W, preferably 30-300W.
Advantage of the present invention is: the present invention is a kind of environmental friendliness, easy and simple to handle, and safety is cheap, prepares efficiently quinoline azolesThe method of ketonic compound. Compared with prior art, the method not only can be suitable for a large amount of functional groups, and productive rate is high, and accessory substance is few,And simple to operate, safety, with low cost, environmental protection.
Detailed description of the invention
Embodiment 1:4(3H) quinazolone: in reaction vessel, add 2-iodo-benzoic acid 1mmol, hydrochloric acid carbonamidine (claim again:Amitraz hydrochloride, molecular formula: CH4N2HCl) 1mmol, copper 8-quinolinolate (B) 0.05mmol, NaOH 1mmol, water 3ML. After putting under microwave reactor, put in microwave reactor and under 150W power, heat 100 DEG C to 30 minutes, be cooled to chamberTemperature. Be extracted with ethyl acetate out product, reduced pressure concentration, product, through column chromatography purification, obtains white solid, productive rate 94%.
Embodiment 2:6-methyl-4(3H) quinazolone: in reaction vessel, add the iodo-5-methyl benzoic acid of 2-1mmol,Hydrochloric acid carbonamidine 1mmol, copper 8-quinolinolate (B) 0.05mmol, NaOH 1mmol, water 3mL. Put into microwave reactionAfter under device, put in microwave reactor and under 150W power, heat 100 DEG C to 30 minutes, be cooled to room temperature. Extract with ethyl acetateTake out product, reduced pressure concentration, product, through column chromatography purification, obtains white solid, productive rate 92%.
Embodiment 3:6-methoxyl group-4(3H) quinazolone: preparation method, with embodiment 2, adds the iodo-5-methoxybenzene of 2-firstAcid 1mmol, obtains colorless solid, productive rate 93%.
Embodiment 4:6-nitro-4(3H) quinazolone: preparation method, with embodiment 2, adds the iodo-5-nitrobenzoic acid 1 of 2-Mmol, obtains yellow solid, productive rate 92%.
The bromo-4(3H of embodiment 5:6-) quinazolone: preparation method, with embodiment 2, adds the iodo-5-bromobenzoic acid of 2-1mmol,Obtain yellow solid, productive rate 84%.
The chloro-4(3H of embodiment 6:6-) quinazolone: preparation method, with embodiment 2, adds the iodo-5-chlorobenzoic acid of 2-1mmol,Obtain white solid, productive rate 81%.
The fluoro-4(3H of embodiment 7:6-) quinazolone: preparation method, with embodiment 2, adds the iodo-5-fluobenzoic acid of 2-1mmol,Obtain white liquid, productive rate 55%.
Embodiment 8:6-acetyl group-4(3H) quinazolone: preparation method, with embodiment 2, adds the iodo-5-acetylbenzene of 2-firstAcid 1mmol, obtains white liquid, productive rate 75%.
Embodiment 9:6-carboxyl-4(3H) quinazolone: preparation method, with embodiment 2, adds 4-iodine M-phthalic acid 1Mmol, obtains white solid, productive rate 63%.
Embodiment 10:4(3H) quinazolone: in reaction vessel, add 2-bromobenzoic acid 1mmol, hydrochloric acid carbonamidine 1Mmol, copper 8-quinolinolate (B) 0.05mmol, NaOH 1mmol, water 3mL. After putting under microwave reactor, put micro-In ripple reactor, under 150W power, heat 100 DEG C to 30 minutes, be cooled to room temperature. Be extracted with ethyl acetate out product, decompressionConcentrated, product, through column chromatography purification, obtains white solid, productive rate 84%.
Embodiment 11:6-methyl-4(3H) quinazolone: in reaction vessel, add the bromo-5-methyl benzoic acid of 2-1mmol,Hydrochloric acid carbonamidine 1mmol, copper 8-quinolinolate (B) 0.05mmol, NaOH 1mmol, water 3mL. Put into microwave reactionAfter under device, put in microwave reactor and under 150W power, heat 100 DEG C to 30 minutes, be cooled to room temperature. Extract with ethyl acetateTake out product, reduced pressure concentration, product, through column chromatography purification, obtains white solid, productive rate 82%.
Embodiment 12:6-methoxyl group-4(3H) quinazolone: preparation method, with embodiment 2, adds the bromo-5-methoxybenzene of 2-firstAcid 1mmol, obtains colorless solid, productive rate 83%.
Embodiment 13:6-nitro-4(3H) quinazolone: preparation method, with embodiment 2, adds the bromo-5-nitrobenzoic acid 1 of 2-Mmol, obtains yellow solid, productive rate 82%.
The bromo-4(3H of embodiment 14:6-) quinazolone: preparation method, with embodiment 2, adds 2,5-dibromobenzoic acid 1mmol,Obtain yellow solid, productive rate 74%.
The chloro-4(3H of embodiment 15:6-) quinazolone: preparation method, with embodiment 2, adds the bromo-5-chlorobenzoic acid of 2-1mmol,Obtain white solid, productive rate 72%.
The fluoro-4(3H of embodiment 16:6-) quinazolone: preparation method, with embodiment 2, adds the bromo-5-fluobenzoic acid 1 of 2-Mmol, obtains white solid, productive rate 45%.
Embodiment 17:6-acetyl group-4(3H) quinazolone: preparation method, with embodiment 2, adds the bromo-5-acetylbenzene of 2-firstAcid 1mmol, obtains white liquid, productive rate 65%.
Embodiment 18:6-carboxyl-4(3H) quinazolone: preparation method, with embodiment 2, adds 4-bromine M-phthalic acid 1Mmol, obtains white solid, productive rate 59%.
Embodiment 19:7-methyl-4(3H) quinazolone: in reaction vessel, add the iodo-4-methyl benzoic acid of 2-1mmol,Hydrochloric acid carbonamidine 1mmol, copper 8-quinolinolate (B) 0.05mmol, NaOH 1mmol, water 3mL. Put into microwave reactionAfter under device, put in microwave reactor and under 150W power, heat 100 DEG C to 30 minutes, be cooled to room temperature. Extract with ethyl acetateTake out product, reduced pressure concentration, product, through column chromatography purification, obtains white solid, productive rate 82%.
Embodiment 20:7-methoxyl group-4(3H) quinazolone: preparation method, with embodiment 2, adds the bromo-4-methoxybenzene of 2-firstAcid 1mmol, obtains colorless solid, productive rate 83%.
Embodiment 21:7-nitro-4(3H) quinazolone: preparation method, with embodiment 2, adds the bromo-4-nitrobenzoic acid 1 of 2-Mmol, obtains yellow solid, productive rate 82%.
The bromo-4(3H of embodiment 22:7-) quinazolone: preparation method, with embodiment 2, adds 2,4-dibromobenzoic acid 1mmol,Obtain yellow solid, productive rate 74%.
The chloro-4(3H of embodiment 23:7-) quinazolone: preparation method, with embodiment 2, adds the bromo-4-chlorobenzoic acid of 2-1mmol,Obtain white solid, productive rate 72%.
The fluoro-4(3H of embodiment 24:7-) quinazolone: preparation method, with embodiment 2, adds the bromo-4-fluobenzoic acid 1 of 2-Mmol, obtains white solid, productive rate 45%.
Embodiment 25:7-acetyl group-4(3H) quinazolone: preparation method, with embodiment 2, adds the bromo-4-acetylbenzene of 2-firstAcid 1mmol, obtains white solid, productive rate 65%.
Embodiment 26:2-methyl-4(3H) quinazolone: in reaction vessel, add 2-iodo-benzoic acid 1mmol, hydrochloric acid secondAmidine 1mmol, copper 8-quinolinolate (B) 0.05mmol, NaOH 1mmol, water 3mL. After putting under microwave reactor,Put in microwave reactor and under 150W power, heat 100 DEG C to 30 minutes, be cooled to room temperature. Be extracted with ethyl acetate and produceThing, reduced pressure concentration, product, through column chromatography purification, obtains white solid, productive rate 82%
Embodiment 27:2-phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds benzamidine hydrochloride 1mmol,Colorless solid, productive rate 93%.
Embodiment 28:2-(4-methyl) phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds 4-aminomethyl phenylAmidine 1mmol, obtains yellow solid, productive rate 93%.
Embodiment 29:2-(4-nitro) phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds 4-nitro base benzeneBase amidine 1mmol, obtains yellow solid, productive rate 87%.
Embodiment 30:2-(4-methoxyl group) phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds 4-methoxyl groupBenzene carbon amidine 1mmol, obtains white solid, productive rate 85%.
Embodiment 31:2-ethyl-4(3H) quinazolone: preparation method, with embodiment 26, adds hydrochloric acid the third amidine 1mmol,Colorless solid, productive rate 93%.
Embodiment 32:2-(4-fluorine) phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds 4-fluorophenyl amidine 1Mmol, obtains yellow solid, productive rate 93%.
Embodiment 33:2-(4-chlorine) phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds 4-chlorphenyl amidine 1Mmol, obtains yellow solid, productive rate 86%.
Embodiment 34:2-(4-bromine) phenyl-4(3H) quinazolone: preparation method, with embodiment 26, adds 4-bromophenyl amidine 1Mmol, obtains white solid, productive rate 80%.
Embodiment 35:2-propyl group-4(3H) quinazolone: preparation method, with embodiment 26, adds hydrochloric acid fourth amidine 1mmol,Colorless solid, productive rate 89%.
Embodiment 36:2-butyl-4(3H) quinazolone: preparation method, with embodiment 26, adds hydrochloric acid the third amidine 1mmol,Yellow solid, productive rate 83%.
Embodiment 37:2-amyl group-4(3H) quinazolone: preparation method, with embodiment 26, adds hydrochloric acid fourth amidine 1mmol,Yellow solid, productive rate 77%.
Embodiment 38:2-hexyl-4(3H) quinazolone: preparation method, with embodiment 26, adds hydrochloric acid penta amidine 1mmol,Yellow solid, productive rate 67%.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all in essence of the present inventionAny amendment of doing within god and principle, is equal to replacement and improvement etc., within all should being included in protection scope of the present invention.
Claims (4)
1. in water, microwave catalysis is prepared the method for Quinazolinone compounds, as shown in following reaction equation, and its concrete stepsAs follows: in reaction vessel, to add catalytic amount water-soluble catalyst (B) and replace 2-halogen benzoic acid substrate, replace amidine hydrochlorideSalt, inorganic base and water, be placed in microwave reactor and react, and after certain hour, is cooled to room temperature, is extracted with ethyl acetate and producesThing, reduced pressure concentration, product is through column chromatography purification;
Wherein R1For halogen, methoxyl group, nitro, methyl, acetyl group, and R1Be positioned at X between position or contraposition; X is Br, I; R2For nitreBase, 4-fluorophenyl, 4-chlorphenyl, 4-bromophenyl, methyl, ethyl, propyl group, butyl;
Described catalyst (B) is oxine copper complex;
Described inorganic base is NaOH;
Described replacement 2-halogen benzoic acid substrate, the mol ratio that replaces amidine hydrochloride salt, catalyst, NaOH are 1:1:0.05:1；
The concentration of described 2-halogen benzoic acid substrate is 0.1-0.9mol/L.
2. method according to claim 1, is characterized in that in concrete steps that reaction temperature is in microwave reactor20－130℃。
3. method according to claim 1, is characterized in that in concrete steps that the reaction time is 5-in microwave reactor160 minutes.
4. according to the method described in claim 1 or 2 or 3, it is characterized in that in concrete steps microwave spoke in microwave reactorPenetrating power is 30-300W.
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| CN106631915B (en) * | 2016-12-22 | 2018-04-03 | 福建医科大学 | The synthesis technique of sulfamide compound in a kind of Microwave system |
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