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WO2024011559A1 - Préparation d'amine aromatique fusionnée à partir d'isocyanure et de cyclopropène - Google Patents

Préparation d'amine aromatique fusionnée à partir d'isocyanure et de cyclopropène Download PDF

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Publication number
WO2024011559A1
WO2024011559A1 PCT/CN2022/105897 CN2022105897W WO2024011559A1 WO 2024011559 A1 WO2024011559 A1 WO 2024011559A1 CN 2022105897 W CN2022105897 W CN 2022105897W WO 2024011559 A1 WO2024011559 A1 WO 2024011559A1
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group
formula
compound
heteroaryl
aryl
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English (en)
Inventor
Chun-Yu HO
Jianqiang Huang
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Southern University of Science and Technology
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Southern University of Science and Technology
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Priority to PCT/CN2022/105897 priority Critical patent/WO2024011559A1/fr
Priority to CN202280098051.5A priority patent/CN119948008A/zh
Publication of WO2024011559A1 publication Critical patent/WO2024011559A1/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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes

Definitions

  • the present application is directed to organic synthesis chemistry, in particular to a process for preparing fused aromatic amines from cyclopropenes and isocyanides.
  • fused aromatic amines are one of the most important aspects in organic synthesis chemistry, they are the core structures of many important functional materials and bioactive molecules.
  • Fused aromatic compounds may serve as primary starting point for preparations of various materials via subsequent transformations, such as electrophilic and nucleophilic aromatic substitution, aromatic CH activations, and dearomatization.
  • the present application is directed to a process for preparing a compound of formula (III) with a compound of formula (I) and a compound of formula (II) in the presence of a carbene and a transition metal catalyst or a precursor thereof,
  • Ar 1 is optionally substituted aryl, heteroaryl, and alkenyl
  • R 1 , R 2 and R 3 is independently selected from the group consisting of H, halide or optionally substituted alkyl, aryl, heteroaryl, alkenyl, alkynyl or metalloid,
  • Substituents on a compound of formula (I) is optionally being connected by alkylene chains.
  • R 4 is optionally substituted alkyl, aryl, heteroaryl, alkenyl, alkynyl or metalloid, and is optionally being connected with the substituents on a compound of formula (I) .
  • Ar 2 is optionally substituted aryl, heteroaryl came from the substituted aryl and heteroaryl of Ar 1 , or is optionally substituted aliphatic structures came from the substituent alkenyl of Ar 1 .
  • Transition metal catalyst is selected from Groups 3 to 12.
  • Carbene is selected from any member of a class of molecules containing divalent carbon atom.
  • C 7 -C 12 alkyl describes an alkyl group, as defined below, having a total of 7 to 12 carbon atoms
  • C 4 -C 12 cycloalkyl describes a cycloalkyl group, as defined below, having a total of 4 to 12 carbon atoms.
  • the total number of carbons in the shorthand notation does not include carbons that may exist in substituents of the group described.
  • C m to C n or “C m to n ” in which “m” and “n” are integers refers to the number of carbon atoms in an alkyl, alkenyl or alkynyl group or the number of carbon atoms in the ring of a cycloalkyl or cycloalkenyl group. That is, the alkyl, alkenyl, alkynyl, ring of the cycloalkyl or ring of the cycloalkenyl can contain from “m” to “n” , inclusive, carbon atoms.
  • a “C 1 to C 4 alkyl” group refers to all alkyl groups having from 1 to 4 carbons, that is, CH 3 -, CH 3 CH 2 -, CH 3 CH 2 CH 2 -, (CH 3 ) 2 CH-, CH 3 CH 2 CH 2 CH 2 -, CH 3 CH 2 CH (CH 3 ) -and (CH 3 ) 3 C-. If no “m” and “n” are designated with regard to an alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group, the broadest range described in these definitions is to be assumed.
  • alkyl as used herein alone or as part of a group means any unbranched or branched, substituted or unsubstituted, saturated hydrocarbon group.
  • the alkyl moiety may be branched or straight chain.
  • the alkyl group may have 1 to 20 carbon atoms (whenever it appears herein, a numerical range such as “1 to 20” refers to each integer in the given range; e.g., “1 to 20 carbon atoms” means that the alkyl group may consist of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms, although the present definition also covers the occurrence of the term “alkyl” where no numerical range is designated) .
  • the alkyl group may also be a medium size alkyl having 1 to 10 carbon atoms.
  • the alkyl group could also be a lower alkyl having 1 to 5 carbon atoms.
  • the alkyl group may be designated as “C 1 -C 4 alkyl” or similar designations.
  • “C 1 -C 4 alkyl” indicates that there are one to four carbon atoms in the alkyl chain, i.e., the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and t-butyl.
  • the alkyl group may be substituted or unsubstituted.
  • the substituent group (s) is (are) one or more group (s) individually and independently selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted cylcloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, heterocyclyl, heterocyclooxy, heteroalicyclyl, hydroxy, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, acyl, thiol, substituted or unsubstituted thioalkoxy, alkylthio, arylthio, cyano, halo, carbonyl, thiocarbonyl, acylalkyl, acylamino, acyloxy, aminoacyl, aminoacyloxy, oxyacylamino,
  • Typical alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl, hexyl, and the like. Wherever a substituent is described as being “optionally substituted” , that substitutent may be substituted with one or more of the above substituents.
  • alkenyl as used herein alone or as part of a group refers to a straight or branched hydrocarbon chain group consisting solely of carbon and hydrogen atoms, containing at least one double bond, having from two to twelve carbon atoms, preferably two to eight carbon atoms and which is attached to the rest of the molecule by a single bond, e.g., ethenyl, propenyl, butenyl, pentenyl, penta-1, 4-dienyl, cyclohexenyl, and the like.
  • alkynyl as used herein alone or as part of a group refers to a straight or branched hydrocarbon chain group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to twelve carbon atoms, preferably two to eight carbon atoms and which is attached to the rest of the molecule by a single bond, e.g., ethynyl, propynyl, butynyl, pentynyl, hexynyl, and the like.
  • aryl as used herein alone or as part of a group is intended to mean a carbocyclic aromatic ring or ring system.
  • a aryl group may be unsubstituted or substituted.
  • aryl includes fused ring systems wherein at least two aryl rings, or at least one aryl and at least one C 3-8 -cycloalkyl share at least one chemical bond.
  • Some examples of “aryl” rings include optionally substituted phenyl, naphthalenyl, phenanthrenyl, anthracenyl, tetralinyl, fluorenyl, indenyl, and indanyl.
  • aryl relates to aromatic, including, for example, benzenoid groups, connected via one of the ring-forming carbon atoms, and optionally carrying one or more substituents selected from heterocyclyl, heteroaryl, halo, hydroxy, amino, cyano, nitro, alkylamido, acyl, C 1-6 -alkoxy, C 1-6 -alkyl, C 1-6 -hydroxyalkyl, C 1-6 -aminoalkyl, C 1-6 -alkylamino, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, sulfamoyl, or trifluoromethyl.
  • the aryl group can be substituted optionally at the para, ortho and/or meta positions.
  • heteroaryl as used herein alone or as part of a group is intended to mean a heterocyclic aromatic group where one or more carbon atoms in an aromatic ring have been replaced with one or more heteroatoms selected from the group comprising nitrogen, sulfur, and oxygen.
  • heteroaryl comprises fused ring systems wherein at least one aryl ring and at least one heteroaryl ring, at least two heteroaryl rings, at least one heteroaryl ring and at least one heterocyclyl ring, or at least one heteroaryl ring and at least one cycloalkyl ring share at least one chemical bond.
  • heteroaryl is understood to relate to aromatic, C 3-8 cyclic groups further containing one oxygen or sulfur atom or up to four nitrogen atoms, or a combination of one oxygen or sulfur atom with up to two nitrogen atoms, and their substituted as well as benzo-and pyrido-fused derivatives, for example, connected via one of the ring-forming carbon atoms.
  • Heteroaryl groups can carry one or more substituents, selected from halo, hydroxy, amino, cyano, nitro, alkylamido, acyl, C 1-6 -alkoxy, C 1-6 -alkyl, C 1-6 -hydroxyalkyl, C 1-6 -aminoalkyl, C 1-6 -alkylamino, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, sulfamoyl, or trifluoromethyl.
  • heteroaryl groups can be five-and six-membered aromatic heterocyclic systems carrying 0, 1, or 2 substituents, which can be the same as or different from one another, selected from the list above.
  • heteroaryl groups include, but are not limited to, unsubstituted and mono-or di-substituted derivatives of furan, benzofuran, thiophene, benzothiophene, pyrrole, pyridine, indole, oxazole, benzoxazole, isoxazole, benzisoxazole, thiazole, benzothiazole, isothiazole, imidazole, benzimidazole, pyrazole, indazole, tetrazole, quionoline, isoquinoline, pyridazine, pyrimidine, purine and pyrazine, furazan, 1, 2, 3-oxadiazole, 1, 2, 3-thiadiazole, 1, 2, 4-thiadiazole, borazine, triazole, benzotriazole, pteridine, phenoxazole, oxadiazole, benzopyrazole, quinolizine, cinnoline,
  • the substituents are halo, hydroxy, cyano, O-C 1-6 -alkyl, C 1-6 -alkyl, hydroxy-C 1-6 -alkyl, and amino-C 1-6 -alkyl.
  • substituent is a group that may be substituted with one or more group (s) individually and independently selected from morpholinoalkanoate, cycloalkyl, aryl, heteroaryl, heterocyclyl, heteroalicyclic, hydroxy, alkoxy, aryloxy, mercapto, alkylthio, arylthio, cyano, halo, carbonyl, thiocarbonyl, O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, C-amido, N-amido, S-sulfonamido, N-sulfonamido, C-carboxy, O-carboxy, isocyanato, thiocyanato, isothiocyanato, nitro, silyl, trihalomethanesulfonyl, and amino, including mono
  • optionally substituted aryl means that the aryl may or may not be substituted and that the description includes both substituted aryl and aryl having no substitution.
  • transition metal refers to any element in the d-block of the periodic table of the elements. This corresponds to groups 3 (IIIB) to 12 (IIB) on the periodic table.
  • ligand in chemistry generally refers to an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons.
  • the metal-ligand bonding ranges from covalent to more ionic.
  • carrier (s) refers to an organic molecule containing a carbon atom with six valence electrons and having the general formula RR’C: .
  • alkylene or “alkylene chain” as used herein alone or as part of a group refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule to a radical group, consisting solely of carbon and hydrogen, containing no unsaturation and having from one to twelve carbon atoms, e.g., methylene, ethylene, propylene, n-butylene, and the like.
  • the alkylene chain is attached to the rest of the molecule through a single bond and to the radical group through a single bond.
  • the points of attachment of the alkylene chain to the rest of the molecule and to the radical group can be through one carbon or any two carbons within the chain.
  • alkenylene or “alkenylene chain” as used herein alone or as part of a group refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule to a radical group, consisting solely of carbon and hydrogen, containing at least one double bond and having from two to twelve carbon atoms, e.g., ethenylene, propenylene, n-butenylene, and the like.
  • the alkenylene chain is attached to the rest of the molecule through a single bond and to the radical group through a double bond or a single bond.
  • the points of attachment of the alkenylene chain to the rest of the molecule and to the radical group can be through one carbon or any two carbons within the chain.
  • alkynylene or “alkynylene chain” as used herein alone or as part of a group refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule to a radical group, consisting solely of carbon and hydrogen, containing at least one triple bond and having from two to twelve carbon atoms, e.g., propynylene, n-butynylene, and the like.
  • the alkynylene chain is attached to the rest of the molecule through a single bond and to the radical group through a double bond or a single bond.
  • the points of attachment of the alkynylene chain to the rest of the molecule and to the radical group can be through one carbon or any two carbons within the chain.
  • amine refers to a compound that comprises an amino group.
  • amino as used herein alone or as part of a group refers to the substituted N-groups.
  • Metalloid or semi metal, is a term used in chemistry when classifying the chemical elements. On the basis of their general physical and chemical properties, nearly every element in the periodic table can be termed either a metal or a nonmetal. However, a few elements are referred to as metalloids. There is no rigorous definition of the term, but the following properties are usually considered characteristic of metalloids: (1) metalloids often form amphoteric oxides; and (2) metalloids often behave as semiconductors (B, Si, Ge) .
  • the following elements are generally considered metalloids: Boron (B) , Silicon (Si) , Germanium (Ge) , Arsenic (As) , Antimony (Sb) , Tellurium (Te) , and Polonium (Po) .
  • the present application is directed to a process for preparing a compound of formula (III) with a compound of formula (I) and a compound of formula (II) in the presence of a N-heterocyclic carbene and transition metal catalyst or a precursor thereof,
  • Ar 1 is optionally substituted aryl, heteroaryl, and alkenyl
  • R 1 , R 2 and R 3 is independently selected from the group consisting of H, halide or optionally substituted alkyl, aryl, heteroaryl, alkenyl, alkynyl or metalloid,
  • Substituents on a compound of formula (I) is optionally being connected by alkylene chains.
  • R 4 is optionally substituted alkyl, aryl, heteroaryl, alkenyl, alkynyl or metalloid, and is optionally being connected with the substituents on a compound of formula (I) .
  • Ar 2 is optionally substituted aryl, heteroaryl came from the substituted aryl and heteroaryl of Ar 1 , or is optionally substituted aliphatic structures came from the substituent alkenyl of Ar 1 .
  • Transition metal catalyst is selected from Groups 3 to 12.
  • Carbene is optionally substituted with one or more than one heteroatom.
  • the ring size is optionally ranged from 4 to 12.
  • Ar 1 is optionally substituted phenyl, naphthalenyl, phenanthrenyl, anthracenyl, tetralinyl, fluorenyl, alkenyl, indenyl, or indanyl.
  • the compound of formula (I) is selected from the group consisting of cyclopropene and substituted derivatives.
  • R 1 , R 2 , and R 3 is independently selected from the group consisting of H, halide or optionally substituted alkyl, aryl, heteroaryl, alkenyl, alkynyl or metalloid.
  • substituents on a compound of formula (I) is optionally being connected by alkylene chains.
  • R 4 is optionally substituted alkyl, aryl, heteroaryl, alkenyl, alkynyl or metalloid.
  • the compound of formula (II) is selected from the group consisting of isocyanides, such as phenyl isocyanide, furanyl isocyanide, tertiary butyl isocyanide and their substituted derivatives.
  • the transition metal catalyst of the present invention may include any catalytic transition metal and/or catalyst precursor as it is introduced into the reaction vessel and which may be, if needed, converted in situ into active form, as well as the active form of the catalyst which participates in the reaction.
  • the transition metal is selected from Groups 3 to 12.
  • Exemplary transition metal that can be used in the present application includes, but is not limited to, Scandium (Sc) , Titanium (Ti) , Vanadium (V) , Chromium (Cr) , Manganese (Mn) , Iron (Fe) , Cobalt (Co) , Nickel (Ni) , Copper (Cu) , Zinc (Zn) , Yttrium (Y) , Zirconium (Zr) , Niobium (Nb) , Molybdenum (Mo) , Technetium (Tc) , Ruthenium (Ru) , Rhodium (Rh) , Palladium (Pd) , Silver (Ag) , Cadmium (Cd) , Hafnium (Hf) , Tantalum (Ta) , Tungsten (W) , Rhenium (Re) , Osmium (Os) , Iridium (Ir) , Platinum (Pt) , Gold (A
  • the transition metal is selected from Group 10.
  • the transition metal is selected from the group consisting of Nickel (Ni) , Palladium (Pd) and Platinum (Pt) . In some embodiments of the present application, the transition metal is Nickel (Ni) .
  • a ligand on the transition metal catalyst is selected from the group consisting of carbenes, heterocyclic carbenes (NHCs) , biscarbenes, bisheterocyclic carbenes, phosphines, amines, imines, arsines, and their hybrids, combinations, and derivatives.
  • the ligand or metal bears a weakly or non-nucleophilic stabilizing ion, including but not limited to halogen, boronates, sulfonates, and phosphonates.
  • the ligand can be added to the reaction mixture in the form of a metal complex, or added as separate reagent relative to the addition of the metal.
  • the ligand if chiral, can be provided as a racemic mixture or a purified stereoisomer.
  • the transition metal catalyst is NiCl 2 DME, or its dimer, trimer or higher order oligomers, optionally used with NaBArF together, where NaBArF is employed in stoichiometric or catalytic amount.
  • the transition metal catalyst is provided in the reaction in a catalytic amount. In certain embodiments, that amount is in the range of ⁇ 10 mol%, with respect to the limiting reagent, which may be either the compound of formula (I) or the compound of formula (II) , depending upon which reagent is in stoichiometric excess.
  • the reaction can be carried out optionally with a solvent.
  • the solvent is selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons, halohydrocarbons, alcohols, ethers, esters, ketones, nitriles and diol derivatives.
  • Exemplary aromatic hydrocarbons that can be used in the present application include, but are not limited to, benzene, toluene, xylene, and the like.
  • Exemplary aliphatic hydrocarbons that can be used in the present application include, but are not limited to, pentane, hexane, heptane, octane, and the like.
  • Exemplary alicyclic hydrocarbons that can be used in the present application include, but are not limited to, cyclohexane, cyclohexanone, methylcyclohexanone, and the like.
  • Exemplary alcohols that can be used in the present application include, but are not limited to, methanol, ethanol, isopropanol, and the like.
  • Exemplary ethers that can be used in the present application include, but are not limited to, diethyl ether, methyl ethyl ether, propyl ether, propylene oxide, and the like.
  • Exemplary esters that can be used in the present application include, but are not limited to, methyl formate, ethyl formate, butyl formate, pentyl formate, methyl acetate, ethyl acetate, propyl acetate, benzyl phenylacetate, and the like.
  • Exemplary ketones that can be used in the present application include, but are not limited to, acetone, methylbutanone, methyl isobutyl ketone, and the like.
  • Exemplary nitriles that can be used in the present application include, but are not limited to, acetonitrile, propionitrile, acrylonitrile, and the like.
  • Exemplary diol derivatives that can be used in the present application include, but are not limited to, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, and the like.
  • the solvent is an aromatic hydrocarbon. In some embodiments of the present application, the solvent is selected from the group consisting of benzene, toluene and xylene.
  • reaction can be carried out in neat condition.
  • Ionic liquid such as imidazolium salts, can be also used as reaction medium.
  • the process may be carried out optionally in a buffer to minimize the problems related to isomerization, oligomerization and polymerization.
  • a buffer which can be used in the present application include but not limited to ammonium salt, phosphorous buffer, carbonates.
  • the reaction is oxygen and moisture sensitive, the substrates shall be dried and degassed before use (normally over CaH 2 , or over powdered CaCl 2 overnight) . Unless otherwise indicated, all reactions were performed under an oxygen-free atmosphere of nitrogen or argon with rigid exclusion of moisture from reagents and glassware.
  • NiBr 2 DME was purchased from ACROS or IL, stored under nitrogen atmosphere and used without further purification.
  • IPr and NaBARF were purchased from Aldrich or Strem. Isocyanide or isonitrile were filtered through a short plug of silica gel and dried before use to remove possible stabilizer. Substituted cyclopropenes were prepared according to common procedure. Toluene was distilled over sodium before use.
  • the catalyst with a general formula of [ (NHC) NiX 2 ] (NaBArF) n , [ (IPr) NiBr 2 ] / (NaBArF) 2 as an example in this case, can be generated according to but not limited to the following method: IPr, NiBr 2 DME and NaBArF in 1: 1: 2 ratio was stirred in toluene for 3-5 mins at 80°C.
  • the [ (NHC) NiBr 2 ] / (NaBARF) 2 catalyst can be also generated by other methods, include but not limited to mixing a Ni source with 1) an imidazolium salt or an ionic liquid in general with or without a base; or 2) alkyl, aryl, benzyl, vinyl, alkenyl or alkynyl X; or 3) a hydride or hydrogen source in general, optionally with the use of activators and buffers, this include but not limited to Lewis acidic additives, protic acid and or nucleophiles; or 4) other common organometallic transformations and manipulations techniques, such as hydride addition or elimination steps as well as substitutions and alike.
  • the mixture was then filtered through a short plug of silica gel and rinsed with 20%ethyl acetate/hexane (50 mL) .
  • the solvent was removed under reduced pressure, and purification via flash chromatography on silica gel and afforded the product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention concerne un procédé de préparation d'amine aromatique fusionnée à partir d'isocyanure et de cyclopropène.
PCT/CN2022/105897 2022-07-15 2022-07-15 Préparation d'amine aromatique fusionnée à partir d'isocyanure et de cyclopropène Ceased WO2024011559A1 (fr)

Priority Applications (2)

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PCT/CN2022/105897 WO2024011559A1 (fr) 2022-07-15 2022-07-15 Préparation d'amine aromatique fusionnée à partir d'isocyanure et de cyclopropène
CN202280098051.5A CN119948008A (zh) 2022-07-15 2022-07-15 一种以异腈和环丙烯为原料制备稠环芳胺的方法

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JP4136717B2 (ja) * 2003-02-27 2008-08-20 独立行政法人科学技術振興機構 シクロペンタジエン誘導体の製造方法

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"Master's Thesis", 1 June 2021, JILIN INSTITUTE OF CHEMICAL TECHNOLOGY, CN, article FENG WANZHONG: "[3+3] Cyclization Reaction of Active Methylene Isocyanides with Cyclopropene Derivatives", pages: 1 - 95, XP009551839, DOI: 10.27911/d.cnki.ghjgx.2021.000048 *
JIAN‐QIANG HUANG; CHUN‐YU HO: "[(NHC)NiIIH]‐Catalyzed Cross‐Hydroalkenylation of Cyclopropenes with Alkynes: Cyclopentadiene Synthesis by [(NHC)NiII]‐Assisted C−C Rearrangement", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 58, no. 17, 8 March 2019 (2019-03-08), Hoboken, USA, pages 5702 - 5706, XP072104068, ISSN: 1433-7851, DOI: 10.1002/anie.201901255 *
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