WO2023080106A1 - Procédé de production d'une amine contenant un cycle aromatique - Google Patents

Procédé de production d'une amine contenant un cycle aromatique Download PDF

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Publication number
WO2023080106A1
WO2023080106A1 PCT/JP2022/040658 JP2022040658W WO2023080106A1 WO 2023080106 A1 WO2023080106 A1 WO 2023080106A1 JP 2022040658 W JP2022040658 W JP 2022040658W WO 2023080106 A1 WO2023080106 A1 WO 2023080106A1
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production method
aromatic ring
acetal
ring
group
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PCT/JP2022/040658
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English (en)
Japanese (ja)
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智明 桐野
大典 大野
清隆 中島
淳 福岡
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三菱瓦斯化学株式会社
国立大学法人北海道大学
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Priority to JP2023558025A priority Critical patent/JPWO2023080106A1/ja
Publication of WO2023080106A1 publication Critical patent/WO2023080106A1/fr

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    • 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

Definitions

  • the present invention relates to a method for producing an amine containing an aromatic ring.
  • Non-Patent Document 1 describes obtaining an aromatic ring-containing amine by the following reaction.
  • the method for producing an amine containing an aromatic ring described in Non-Patent Document 1 has various problems when applied to industrial production.
  • the method for producing amines described in Non-Patent Document 1 produces a large amount of by-products. Therefore, there is a need for a novel method for producing amines containing aromatic rings.
  • a method for producing aromatic ring-containing amines with a high yield and a small amount of by-products is to solve such problems, and an object of the present invention is to provide a method for producing an amine containing an aromatic ring with a high yield and a small amount of by-products.
  • ⁇ 4> The production method according to any one of ⁇ 1> to ⁇ 3>, wherein the acetal compound containing an aromatic ring contains an aromatic hetero ring.
  • ⁇ 5> The production method according to any one of ⁇ 1> to ⁇ 3>, wherein the acetal compound containing an aromatic ring contains a furan ring.
  • ⁇ 6> The production method according to any one of ⁇ 1> to ⁇ 5>, wherein the acetal compound containing an aromatic ring contains 1 to 3 acetal groups in one molecule.
  • ⁇ 7> The production method according to any one of ⁇ 1> to ⁇ 3>, wherein the acetal compound containing an aromatic ring is represented by the following formula (S1).
  • R s2 and R s3 are each independently a hydrocarbon group having 1 to 10 carbon atoms, and R s2 and R s3 may combine with each other to form a ring.
  • ms2 is 0 or 1
  • ns is 1 or 2.
  • each acetal group may be the same or different.
  • ⁇ 11> The production method according to any one of ⁇ 1> to ⁇ 10>, wherein the amination reaction is performed in the presence of a solvent.
  • the solvent contains a compound represented by A-(OH) m (where A is a hydrocarbon group having 1 to 10 carbon atoms and m is 1 or 2); Method of manufacture as described.
  • A-(OH) m where A is a hydrocarbon group having 1 to 10 carbon atoms and m is 1 or 2
  • the volume ratio of the compound represented by A-(OH) m to water in the solvent is 0 or more and less than 1 with respect to the compound 1 represented by A-(OH) m . 12>.
  • ⁇ 14> The volume ratio of water to the compound represented by A-(OH) m is more than 0 and less than 1 relative to the compound 1 represented by A-(OH) m , ⁇ 12> The manufacturing method described in .
  • ⁇ 15> The production method according to any one of ⁇ 12> to ⁇ 14>, wherein the compound represented by A-(OH) m contains methanol.
  • ⁇ 16> The production method according to any one of ⁇ 11> to ⁇ 15>, wherein the solvent contains water.
  • ⁇ 17> The production method according to any one of ⁇ 1> to ⁇ 13> and ⁇ 15>, wherein water is not supplied to the reaction system for the amination reaction.
  • ⁇ 18> The production method according to any one of ⁇ 1> to ⁇ 17>, including adding the acetal compound containing the aromatic ring to the reaction system.
  • an "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the notations that do not describe substituted and unsubstituted are preferably unsubstituted. If the measurement methods, etc. described in the standards shown in this specification differ from year to year, they shall be based on the standards as of January 1, 2021 unless otherwise stated.
  • the method for producing an amine containing an aromatic ring includes supplying a hydrogen source and a nitrogen source to an acetal compound containing an aromatic ring to allow an amination reaction to proceed.
  • the acetal compound containing an aromatic ring is a compound that serves as a starting material for the reaction in this embodiment.
  • An acetal compound containing an aromatic ring is usually introduced into the reaction system, but it may be an intermediate starting from another compound.
  • an acetal compound as a starting material, an amine compound containing an aromatic ring can be obtained in a state where the amination reaction proceeds quickly and by-products are reduced.
  • the reason for this is that when an aldehyde compound, which is a precursor of an acetal compound, is used as a starting material, a side reaction in which formyl groups react with the resulting amine compound proceeds, whereas when an acetal compound is used as a starting material, the side reaction proceeds. It is presumed that this is because no reaction occurs.
  • Acetal is a compound having a structure represented by (R 1 O—)(R 2 O—)R 3 C— (hereinafter referred to as “acetal group”).
  • R 1 and R 2 are each independently a substituent (usually a hydrocarbon group, preferably a hydrocarbon group having 1 to 10 carbon atoms), and R 3 is a hydrogen atom or a substituent (preferably is a hydrogen atom).
  • R 1 and R 2 may combine with each other to form a ring, but preferably do not form a ring. By not forming a ring, the amination reaction tends to proceed easily.
  • the acetal compound containing an aromatic ring preferably contains 1 to 3 acetal groups per molecule.
  • the acetal compound containing an aromatic ring used in this embodiment preferably has an acetal group directly bonded to the aromatic ring.
  • the fact that the acetal group is directly bonded to the aromatic ring means that the acetal group is bonded to a ring-constituting atom (for example, a carbon atom) of the aromatic ring. Since the acetal compound used in the present embodiment contains an aromatic ring, the stability of the transition state of the reaction differs from that of the conventional acetal compound.
  • One example of the number of acetal groups in one molecule of the acetal compound containing an aromatic ring is one.
  • Another example of the number of acetal groups in one molecule of the acetal compound containing an aromatic ring is two.
  • the aromatic ring contained in the acetal compound containing the aromatic ring is preferably an aromatic ring having 3 to 14 carbon atoms.
  • the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, preferably an aromatic heterocyclic ring.
  • the aromatic ring is preferably a 5- or 6-membered ring, more preferably a 5-membered ring.
  • the aromatic ring may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring. In the case of condensed rings, preferably 2 to 4 rings are condensed, more preferably 2 or 3 rings are condensed, and more preferably 2 rings are condensed.
  • the aromatic hydrocarbon ring is preferably a benzene ring, naphthalene ring, or anthracene ring
  • the aromatic hetero ring is a furan ring, thiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxazole ring, or thiazole ring.
  • a pyridine ring, a pyrimidine ring, a pyran ring, etc., and a furan ring is preferred.
  • the molecular weight of the acetal compound containing the aromatic ring is preferably 140 or more, more preferably 180 or more, and preferably 1000 or less, more preferably 800 or less.
  • the acetal compound containing the aromatic ring is preferably represented by the following formula (S).
  • Ar is a group containing an aromatic ring having 4 to 10 carbon atoms
  • R s1 is —COOH or a hydrocarbon group having 1 to 10 carbon atoms
  • R s2 and R s3 are each independently a hydrocarbon group having 1 to 10 carbon atoms
  • R s2 and R s3 may be bonded to each other to form a ring
  • m is an integer of 0 to 9
  • n is 1 is an integer of up to 3.
  • each R s1 may be the same or different
  • each acetal group may be the same, may be different.
  • Ar is a group containing an aromatic ring having 4 to 10 carbon atoms, preferably a 5-membered heterocyclic group, a 6-membered heterocyclic group, a benzene ring group, a biphenyl group and a naphthyl group.
  • R s1 is —COOH or a hydrocarbon group having 1 to 10 carbon atoms, preferably —COOH or a hydrocarbon group having 1 to 8 carbon atoms, and —COOH or an alkyl group having 1 to 5 carbon atoms is more preferred, and -COOH is even more preferred.
  • R s2 and R s3 are each independently a hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrocarbon group having 1 to 5 carbon atoms, and a hydrocarbon group having 1 to 3 carbon atoms. is more preferred.
  • R s2 and R s3 are preferably alkyl groups, more preferably methyl groups, ethyl groups or propyl groups, and even more preferably methyl groups.
  • R s2 and R s3 may combine with each other to form a ring.
  • the total carbon number of R s2 and R s3 is preferably 2-8.
  • R s2 and R s3 preferably do not form a ring.
  • m is an integer of 0 to 9, preferably 0 to 3, and particularly preferably 0 or 1.
  • n is preferably 1 or 2, more preferably 1.
  • the acetal compound containing the aromatic ring is more preferably represented by the following formula (S1).
  • X is a heteroatom
  • R s1 is —COOH or a hydrocarbon group having 1 to 10 carbon atoms
  • R s2 and R s3 each independently represent a a hydrocarbon group
  • R s2 and R s3 may be bonded to each other to form a ring
  • ms is an integer of 0 to 2
  • ns is 1 or 2
  • ms is 2
  • each R s1 may be the same or different
  • each acetal group may be the same or different.
  • X is preferably a nitrogen atom, an oxygen atom or a sulfur atom, more preferably an oxygen atom.
  • R s1 , R s2 and R s3 have the same meanings as R s1 , R s2 and R s3 in formula (S), and the preferred ranges are also the same.
  • An example of this embodiment is where ms is 0 and ns is 2.
  • Another example of this embodiment is where ms is 1 and ns is 1.
  • An example of this embodiment is also in the heterocycle of formula (S1), wherein R s1 is at least one of the 2-, 3-, 4- and 5-positions and an acetal group is at the 2- and/or 3-positions.
  • R s1 is bonded to the 5-position and the acetal group is bonded to the 2-position.
  • Another example of this embodiment is that in the heterocycle of formula (S1), R s1 is absent and two acetal groups are attached at the 2- and 5-positions.
  • Formula (S1) is preferably represented by formula (S2).
  • R s2 and R s3 are each independently a hydrocarbon group having 1 to 10 carbon atoms, and R s2 and R s3 may combine with each other to form a ring.
  • ms2 is 0 or 1
  • ns is 1 or 2.
  • each acetal group may be the same or different.
  • R s2 and R s3 have the same meanings as R s2 and R s3 in formula (S1), and the preferred ranges are also the same.
  • An example of this embodiment is where ms2 is 0 and ns is 2.
  • Another example of this embodiment is where ms2 is 1 and ns is 1.
  • the above compounds are sold as commercial products by multiple manufacturers, and can be obtained, for example, from Tokyo Kasei Kogyo Co., Ltd.
  • the amine containing an aromatic ring obtained in the present embodiment is a compound in which the acetal group in the acetal compound containing an aromatic ring as a raw material is aminated.
  • the aromatic ring-containing amine obtained by the production method of the present embodiment is preferably represented by the following formula (S-1).
  • Ar is a group containing an aromatic ring having 4 to 10 carbon atoms
  • R s1 is —COOH or a hydrocarbon group having 1 to 10 carbon atoms
  • m is 0 to 9 and n is an integer of 1 to 3.
  • each R s1 may be the same or different.
  • each acetal group may be the same or different).
  • R s1 , Ar, m and n in formula (S-1) are synonymous with R s1 , Ar, m and n in formula (S), respectively, and the preferred ranges are also the same.
  • the aromatic ring-containing amine obtained by the production method of the present embodiment is more preferably represented by the following formula (S1-1).
  • X is a heteroatom
  • R s1 is —COOH or a hydrocarbon group having 1 to 10 carbon atoms
  • ms is an integer of 0 to 2
  • ns is 1 or 2.
  • each R s1 may be the same or different.
  • X, R s1 , ms and ns in formula (S1-1) have the same meanings as X, R s1 , ms and ns in formula (S1), respectively, and the preferred ranges are also the same.
  • Formula (S1-1) is preferably represented by formula (S2-1).
  • ms2 is 0 or 1
  • ns is 1 or 2.
  • ms2 and ns in formula (S2-1) are synonymous with ms2 and ns in formula (S2), respectively, and preferred ranges are also the same.
  • Preferred examples of amines produced by the production method of the present embodiment are as follows. Needless to say, the amines produced in the present invention are not limited to these.
  • a hydrogen source and a nitrogen source are supplied to an acetal compound containing an aromatic ring to advance the amination reaction of the acetal group.
  • the hydrogen source and the nitrogen source may be supplied simultaneously, the hydrogen source may be supplied first, or the nitrogen source may be supplied first.
  • the hydrogen source is not particularly limited as long as it can supply a hydrogen source capable of reducing an acetal compound containing an aromatic ring, but hydrogen is preferred.
  • the production method of the present embodiment is preferably carried out under hydrogen pressure.
  • the pressure with hydrogen is preferably greater than or equal to 1 bar and preferably less than or equal to 10 bar.
  • the nitrogen source is not particularly limited, but preferably contains ammonia and/or an ammonium salt, and more preferably contains an ammonium salt.
  • the ammonium salt a salt obtained by neutralizing an organic acid or an inorganic acid with ammonia can be used.
  • Ammonium salts of organic acids include ammonium carbonate, ammonium formate, ammonium acetate, ammonium propionate, ammonium butyrate, ammonium isobutyrate, ammonium oxalate, ammonium succinate, ammonium adipate, ammonium benzoate, and diammonium phthalate.
  • ammonium salts of inorganic acids include ammonium phosphate, monoammonium phosphate, diammonium phosphate, ammonium borate, ammonium pentaborate, and ammonium tetraborate.
  • ammonium salts of organic acids are preferable, and more preferably at least one selected from the group consisting of ammonium carbonate, ammonium formate, ammonium acetate, ammonium propionate, and ammonium butyrate, including ammonium acetate. is more preferred.
  • the amount of the nitrogen source is preferably 1 mol or more, and may be 4 mol or more, per 1 mol of the raw material (acetal group contained in the acetal compound containing an aromatic ring). . Further, the amount of the nitrogen source is preferably 50 mol or less, may be 40 mol or less, or may be 30 mol or less per 1 mol of the raw material (acetal group contained in the acetal compound containing an aromatic ring). may be 20 mol or less, or may be 15 mol or less. In the production method of the present embodiment, one type of nitrogen source may be used, or two or more types may be used. When two or more are used, the total amount is preferably within the above range.
  • the amination reaction is preferably carried out in the presence of a metal catalyst.
  • a metal catalyst By using a metal catalyst, the reduction with hydrogen can be effectively advanced.
  • the metal catalyst a wide range of metal catalysts used for reduction with hydrogen can be used, and the type thereof is not particularly limited.
  • the metal catalyst is preferably metallic nickel, metallic cobalt, a nickel compound, or a cobalt compound, and more preferably metallic nickel, metallic cobalt, nickel phosphide, or cobalt phosphide. Among these, cobalt phosphide is preferred, and particles of cobalt phosphide are more preferred.
  • the amount of the metal catalyst in the production method of the present embodiment is preferably 0.01 mol or more per 1 mol of the raw material (acetal group contained in the acetal compound containing an aromatic ring) when the metal catalyst is used. It may be 0.05 mol or more, or may be 0.08 mol or more. Further, the catalyst may be 10 mol or less, 5 mol or less, or 3 mol or less per 1 mol of the raw material (acetal group contained in the acetal compound containing an aromatic ring). It may be 0.4 mol or less, or 0.2 mol or less. In the production method of the present embodiment, one type of metal catalyst may be used, or two or more types may be used. When two or more are used, the total amount is preferably within the above range.
  • the amination reaction is preferably carried out in the presence of a solvent.
  • the solvent used in this embodiment preferably contains a compound represented by A—(OH) 2 m (where A is a hydrocarbon group having 1 to 10 carbon atoms and m is 1 or 2).
  • A is a hydrocarbon group having 1 to 10 carbon atoms and m is 1 or 2.
  • the solvent used in this embodiment contains water. By including water in the solvent, the effect of improving the reaction rate is obtained.
  • A is preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrocarbon group having 1 to 5 carbon atoms, and 1 to 5 carbon atoms. 3 is more preferably a hydrocarbon group.
  • the hydrocarbon group is preferably an alkyl group.
  • A is preferably a methyl group or an ethyl group, more preferably a methyl group.
  • A is preferably an ethylene group, a propylene group, or a butylene group.
  • m is preferably 1.
  • compounds represented by A—(OH) m include methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, 3-pentanol, 2 -methyl-1-butanol, 3-methyl-1-butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, alkyl monoalcohols such as neopentyl alcohol, ethylene glycol, 1,3-propanediol, Examples include alkylene diols such as 1,4-butanediol, alkyl monoalcohols are preferred, methanol and ethanol are more preferred, and methanol is even more preferred.
  • the volume ratio of the compound represented by A-(OH) m to water in the solvent is the compound 1 represented by A-(OH) m
  • water is 0 or more and less than 1.
  • the volume ratio of water and the compound represented by A-(OH) m is 0.1 or more with respect to the compound 1 represented by A-(OH) m. or 0.3 or more, preferably 0.9 or less, more preferably 0.7 or less.
  • the volume ratio of the compound represented by A-(OH) m to water is relative to the compound 1 represented by A-(OH) m , water is greater than 0 and less than 1.
  • the volume ratio of water and the compound represented by A-(OH) m is 0.1 or more with respect to the compound 1 represented by A-(OH) m. or 0.3 or more, preferably 0.9 or less, more preferably 0.7 or less.
  • the solvent used in the present embodiment is the total amount of the compound represented by A-(OH) m and water (however, it is not essential to contain both the compound represented by A-(OH) m and water. is preferably 90% by volume or more, more preferably 95% by volume or more, and even more preferably 99% by volume or more, of the solvent.
  • the reaction temperature of the amination reaction in the production method of the present embodiment is preferably 50° C. or higher, more preferably 90° C. or higher, even more preferably 95° C. or higher, and 100° C. or higher. is more preferable, and 105° C. or higher is even more preferable.
  • the reaction temperature of the amination reaction is preferably 200° C. or lower, more preferably 150° C. or lower, even more preferably 140° C. or lower, even more preferably 130° C. or lower, 125° C. or lower is even more preferable.
  • the reaction temperature may be the same temperature (however, a variation of ⁇ 5 ° C.
  • reaction temperature is the same (however, a variation of ⁇ 5° C. is regarded as an error) except for the initial temperature increase and the final temperature decrease.
  • the reaction time of the amination reaction in the production method of the present embodiment is preferably 1 minute or longer, may be 30 minutes or longer, may be 1 hour or longer, or may be 2 hours or longer. .
  • the reaction time of the amination reaction may be 50 hours or less, 30 hours or less, 20 hours or less, or 9 hours or less.
  • Separation of the reaction mixture and the catalyst after the reaction can be performed by general methods such as sedimentation, centrifugation, and filtration. Separation of the catalyst is preferably carried out under an atmosphere of an inert gas such as nitrogen or argon, depending on the catalyst to be used, in order to prevent ignition.
  • the reaction mixture may be used as a raw material or an intermediate as it is, or the reaction mixture may be purified by post-treatment as appropriate. Specific post-treatment methods include known purification methods such as extraction, distillation, and chromatography. These purification methods may be performed in combination of two or more.
  • the higher the raw material conversion rate of the acetal compound containing an aromatic ring the better, preferably 35% or more, more preferably 50% or more, and 80% or more. is more preferable, and 90% or more is even more preferable.
  • the ideal upper limit is 100 mol %, but even if it is 99.99% or less, the required performance is satisfied.
  • the higher the selectivity of the amine compound containing an aromatic ring the better, preferably 30% or more, more preferably 50% or more, and 70% or more. is more preferable, and 80% or more is even more preferable.
  • the ideal upper limit is 100 mol %, but even if it is 99% or less, the required performance is satisfied.
  • the raw material addition rate and selectivity are measured according to the description of the examples described later.
  • Example 1 Amination was carried out according to the following scheme. Specifically, an autoclave was charged with 0.5 mmol of the following raw material (FFCA-acetal), 3 mL of a solvent, 0.05 mmol of the cobalt phosphide catalyst obtained above, and 5 mmol of a nitrogen source (ammonium acetate salt), and a hydrogen pressure of 5 bar. and a reaction temperature of 120° C. for 1.5 hours. Water and methanol (MeOH) were used as solvents in a volume ratio of 1:2.
  • NH 4 OAc represents ammonium acetate.
  • the conversion rate was calculated by quantifying the raw material by HPLC (High Performance Liquid Chromatography) measurement. The unit of conversion is %. Table 1 shows the results.
  • the reaction solution was subjected to HPLC measurement, and raw materials and products were identified and quantified.
  • the selectivity of AMFCA in the product was calculated.
  • the selectivity means the ratio (unit %) of the number of moles of AMFCA to the total number of moles of the product. Table 1 shows the results.
  • Example 2 Reference Examples 1 and 2 In Example 1, changes were made as shown in Table 1, and the others were carried out in the same manner.
  • FFCA indicates 5-formyl-2-furancarboxylic acid.

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de production d'une amine contenant un cycle aromatique avec un rendement élevé, le procédé générant moins de sous-produits. La présente invention concerne un procédé de production d'une amine contenant un cycle aromatique, le procédé comprenant un procédé dans lequel une réaction d'amination est provoquée par l'apport d'une source d'hydrogène et d'une source d'azote dans un composé acétal contenant un cycle aromatique.
PCT/JP2022/040658 2021-11-08 2022-10-31 Procédé de production d'une amine contenant un cycle aromatique WO2023080106A1 (fr)

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Citations (3)

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Publication number Priority date Publication date Assignee Title
JPS58128356A (ja) * 1982-01-28 1983-07-30 Ube Ind Ltd ２−アルコキシメチレン−３，３−ジアルコキシブロパンニトリル類
WO2008114506A1 (fr) * 2007-03-19 2008-09-25 Daiichi Sankyo Company, Limited Procédé de fabrication d'acide 4-aminométhylbenzoïque
CN112020490A (zh) * 2018-03-15 2020-12-01 罗地亚经营管理公司 用于在包含水的溶剂体系中生产胺的方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58128356A (ja) * 1982-01-28 1983-07-30 Ube Ind Ltd ２−アルコキシメチレン−３，３−ジアルコキシブロパンニトリル類
WO2008114506A1 (fr) * 2007-03-19 2008-09-25 Daiichi Sankyo Company, Limited Procédé de fabrication d'acide 4-aminométhylbenzoïque
CN112020490A (zh) * 2018-03-15 2020-12-01 罗地亚经营管理公司 用于在包含水的溶剂体系中生产胺的方法

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ABELL ANDREW D., DEBORAH A. HOULT, EMILY J. JAMIESON: "Synthesis of 1,2-Disubstituted Pyrroles: A Cis Peptide Bond Surrogate", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 33, no. 39, 22 September 1992 (1992-09-22), Amsterdam , NL , pages 5831 - 5832, XP093045195, ISSN: 0040-4039, DOI: 10.1016/0040-4039(92)89043-C *
NAKAMOTO, K. ; TSUKADA, I. ; TANAKA, K. ; MATSUKURA, M. ; HANEDA, T. ; INOUE, S. ; MURAI, N. ; ABE, S. ; UEDA, N. ; MIYAZAKI, M. ;: "Synthesis and evaluation of novel antifungal agents-quinoline and pyridine amide derivatives", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 20, no. 15, 1 August 2010 (2010-08-01), Amsterdam NL , pages 4624 - 4626, XP027137555, ISSN: 0960-894X *

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