WO2005077863A1 - VERFAHREN ZUR CC-BINDUNGSKNÜPFUNG ZWISCHEN ELEKTROPHILEN SUBSTRATEN UND π-NUCLEOPHILEN IN NEUTRALEN BIS BASISCHEN WÄSSRIGEN ODER ALKOHOLISCHEN LÖSUNGSMITTELN OHNE DEN EINSATZ EINER LEWIS- ODER PROTONENSÄURE - Google Patents
VERFAHREN ZUR CC-BINDUNGSKNÜPFUNG ZWISCHEN ELEKTROPHILEN SUBSTRATEN UND π-NUCLEOPHILEN IN NEUTRALEN BIS BASISCHEN WÄSSRIGEN ODER ALKOHOLISCHEN LÖSUNGSMITTELN OHNE DEN EINSATZ EINER LEWIS- ODER PROTONENSÄURE Download PDFInfo
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- WO2005077863A1 WO2005077863A1 PCT/EP2005/001277 EP2005001277W WO2005077863A1 WO 2005077863 A1 WO2005077863 A1 WO 2005077863A1 EP 2005001277 W EP2005001277 W EP 2005001277W WO 2005077863 A1 WO2005077863 A1 WO 2005077863A1
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- 0 COc1ccc(C(*)*)cc1 Chemical compound COc1ccc(C(*)*)cc1 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/04—Substitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
- C07D307/36—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Definitions
- the invention relates to a method for carbon-carbon bond formation by 5 conversion of electrophilic substrates with a solvolysis rate k Et0H (25 ° C)> 10 "6 s " 1 and ⁇ compounds, characterized in that the intermediate carbocations in neutral to basic aqueous or alcoholic solvents or solvent mixtures are generated without the use of a Lewis acid or protonic acid.
- Lewis acid (or proton acid) induced reactions of electrophiles e.g.
- metal halides of the formula type MX n such as A1C1 3 , 25 AlBr 3 , BC1 3 , BF 3 , FeCl 3 , TiCl 4 , SnC, SbF 5 , GaCl 3 , ZnCl 2 ( GA Olah, S. Kobayashi, M. Tashiro, J. Am. Chem. Soc. 1972, 94, 7448.) or POCl 3 used in the Workup of the reaction batches can be irreversibly deactivated by hydrolysis.
- MX n metal halides of the formula type MX n , such as A1C1 3 , 25 AlBr 3 , BC1 3 , BF 3 , FeCl 3 , TiCl 4 , SnC, SbF 5 , GaCl 3 , ZnCl 2 ( GA Olah, S. Kobayashi, M. Tashiro, J. Am. Chem. Soc. 1972, 94, 7448.)
- Chlorinated hydrocarbons which have a low ability to coordinate with metal halides are frequently used as solvents. Since the Lewis acids 30 are sensitive to moisture, work is carried out with strict exclusion of moisture, which requires great preparative effort.
- aqueous reaction media has gained great importance in synthetic organic chemistry. CC-linking reactions that are carried out in such solvents can be a great challenge (A. Lubineau, J. Ange, Y. Queneau, Synthesis 1994, 741-760; CJ Li, Chem. Rev. 1993, 93, 2923-2035.). Furthermore, better reactivities and selectivities are often achieved in aqueous media than under anhydrous conditions (S. Kobayashi, K. Manabe, Chem. Eur. J. 2002, 18, 4094-4101; S. Kobayashi, Eur. J. Org. Chem. 1999, 15-27.).
- Substrates containing acid labile groups such as e.g. Alkyleneol ethers, silyl enol ethers, ketene acetals or enamines can be decomposed by Lewis or protonic acids.
- the present invention is therefore based on the object of providing a process by which a carbon-carbon bond formation in the sense of a Friedel-Crafts or related reaction is accomplished without the use of a Lewis or protonic acid in non-chlorinated solvents and thus the A large number of additional substrates can be used under moderate reaction conditions, which offers significant ecological and economic advantages compared to the established synthesis options.
- the relative rate of formation of carbocations can be given, among other things, using the ethanolysis constant k Et0H , ie the rate constant of solvolysis in 100% ethanol at 25 ° C.
- This parameter has been used in particular to indicate the relative reactivity of alkyl halides, especially of chlorides or bromides.
- k EtOH 25 ° C.
- substituents R 1 , R 2 and R 3 on the compounds of type (I) with the specified minimum values of k Et0H which, however, do not constitute an exhaustive list, are substituents which are selected independently of one another from the group of branched or unbranched alkyl , preferably C 1 -C 4 alkyl, especially methyl, aryl, preferably C 6 -C 10 aryl, especially phenyl, substituted aryl, preferably by amino, alkoxy or alkyl substituents, especially 4-methoxyphenyl (anisyl) and 4-methylphenyl ( Tolyl), substituted or unsubstituted heteroaryl, in particular thiophene, furan and pyrrole, branched or unbranched alkenyl, preferably C 2 -C 0 -alkenyl, in particular 3-methylbut-2-enyl, cycloalk-2-enyl, preferably C 4 -C 7 cycloalk-2-eny
- Halogen represents fluorine, chlorine, bromine or iodine, preferably chlorine and bromine.
- a compilation of possible leaving groups is shown in list 1.1. List 1.1
- Halogen ⁇ l . -Br, -ci, -F oxygen substituents -OCH 3 , -OC 2 H 5 , -OCH 2 Ph, -OCH 2 CH CH 2 , -OCH 2 CF 3 0 2 N 0 2 N -0 "@, -O - ⁇ - CI, -0 - ⁇ - N0 2> "0- ⁇ 0 2 ( -OH ⁇ ⁇ N0 2) -O ⁇ Q- oo OO II II II -OC-CH 3 , -0-CC ( CH 3 ) 3 , -OC-CF 3 , -0-CC 3 F 7
- the ⁇ compounds which can be used as nucleophilic compounds in the process according to the invention are aliphatic ⁇ nucleophiles, such as e.g. substituted alkenes and alkynes, allyl and propargylsilanes, alkyleneol ethers, silylenol ethers, (silyl) ketene acetals and enamines, or aromatic ⁇ -nucleophiles such as e.g. donor-substituted aromatics, heteroaromatics, preferably substituted or unsubstituted furans, thiophenes, pyrroles or indoles.
- aliphatic ⁇ nucleophiles such as e.g. substituted alkenes and alkynes, allyl and propargylsilanes, alkyleneol ethers, silylenol ethers, (silyl) ketene acetals and enamines, or aromatic
- the ⁇ compounds used are used as solutions in a concentration range from 0.01 M to 20 M, preferably 0.1 M to 5 M, in particular 0.5 M to 2 M, in the solvents or solvent mixtures listed below.
- the solvents or solvent mixtures used are or are composed of the group of alcohols, in particular ethanol, methanol, 2,2,2-trifluoroethanol or 1,1,1,3,3,3-hexafluoroisopropanol, tetrahydrofuran, water, acetone, acetonitrile and dioxane.
- acetone-water mixtures preferably 80% aqueous acetone (80A20W (v / v)), acetonitrile / water mixtures, preferably 90% aqueous acetonitrile (90AN10W (v / v)), or pure 2,2,2-trifluoroethanol for use.
- the intermediate carbocation is captured in a rapid reaction by the corresponding solvent.
- W water
- T 2,2,2-trifluoroethanol
- AN acetonitrile
- A acetone.
- the number in front of the respective solvent abbreviation corresponds to the quantity in%.
- Basic inorganic and organic compounds were used as additives, preferably hydrogen carbonates, carbonates and pyridines, in particular ammonium hydrogen carbonate (NH HCO 3 ), sodium hydrogen carbonate (NaHCO 3 ), ammonium carbonate [(NH) 2 CO 3 ], 2-chloropyridine and 2,6 -Lutidin.
- NH HCO 3 ammonium hydrogen carbonate
- NaHCO 3 sodium hydrogen carbonate
- 2-chloropyridine 2,6 -Lutidin.
- reaction times are generally 1 second to 2 days, preferably 1 minute to 5 hours.
- the course of the reaction can be followed, for example, with GCMS or NMR spectroscopic investigations.
- the electrophile is added so slowly that the heat of reaction can be easily removed.
- the reaction mixture is preferably stirred at room temperature (rt).
- the same volume of water is added to the reaction mixture and the aqueous phase is extracted several times with diethyl ether.
- the combined organic extracts are dried over a drying agent, preferably sodium sulfate or magnesium sulfate, and excess solvent is removed in vacuo.
- the residues are subjected, for example, to distillation or chromatography on silica gel.
- the syntheses can be carried out on a larger scale while maintaining the stoichiometry of the substances used.
- the electrophile is added so slowly that the heat of reaction can be easily removed.
- the reaction mixture is preferably stirred at room temperature (rt).
- the same volume of water is added to the reaction mixture and the aqueous phase is extracted several times with diethyl ether.
- the combined organic extracts are dried over a drying agent, preferably sodium sulfate or magnesium sulfate, and excess solvent is removed in vacuo.
- the residues are subjected, for example, to distillation or chromatography on silica gel.
- n H amount of substance electrophile
- n Nu amount of substance nucleophile
- Vs 0 i v + Nu total volume of the 1 molar solution of the nucleophile.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05701385A EP1716087A1 (de) | 2004-02-11 | 2005-02-09 | Verfahren zur cc-bindungsknüpfung zwischen elektrophilen substraten und pi-nucleophilen in neutralen bis basischen wässrigen oder alkoholischen lösungsmitteln ohne den einsatz einer lewis- oder protonensäure |
JP2006552532A JP2007523077A (ja) | 2004-02-11 | 2005-02-09 | 中性から塩基性の水性またはアルコール性溶媒中でルイス酸またはプロトン酸を使用せずに求電子基質とπ求核剤との間にCC結合を形成する方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004006785A DE102004006785A1 (de) | 2004-02-11 | 2004-02-11 | Verfahren zur CC-Bindungsknüpfung zwischen elektrophilen Substraten und TT-Verbindungen in neutralen bis basischen wässrigen oder alkoholischen Lösungsmitteln ohne den Einsatz einer Lewis- oder Protonensäure |
DE102004006785.6 | 2004-02-11 |
Publications (1)
Publication Number | Publication Date |
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WO2005077863A1 true WO2005077863A1 (de) | 2005-08-25 |
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PCT/EP2005/001277 WO2005077863A1 (de) | 2004-02-11 | 2005-02-09 | VERFAHREN ZUR CC-BINDUNGSKNÜPFUNG ZWISCHEN ELEKTROPHILEN SUBSTRATEN UND π-NUCLEOPHILEN IN NEUTRALEN BIS BASISCHEN WÄSSRIGEN ODER ALKOHOLISCHEN LÖSUNGSMITTELN OHNE DEN EINSATZ EINER LEWIS- ODER PROTONENSÄURE |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1716087A1 (de) |
JP (1) | JP2007523077A (de) |
CN (1) | CN1942419A (de) |
DE (1) | DE102004006785A1 (de) |
WO (1) | WO2005077863A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106866610A (zh) * | 2017-04-19 | 2017-06-20 | 齐齐哈尔大学 | 一种Lewis/Bronsted酸促进下醇参与的2‑氨基色烯衍生物N‑烷基化方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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MX2011005577A (es) | 2008-11-26 | 2011-08-03 | Arena Pharm Inc | Derivados de acido carbonico substituidos con pirazolilo como moduladores del receptor de prostaciclina (pgi2) utiles para el tratamiento de trastornos relacionados con estos. |
EP2370413B1 (de) | 2008-12-08 | 2015-08-05 | Arena Pharmaceuticals, Inc. | Modulatoren des prostacyclin(pgi2)-rezeptors zur behandlung von damit einhergehenden erkrankungen |
AU2015335841B2 (en) | 2014-10-23 | 2020-06-25 | Arena Pharmaceuticals, Inc. | Method of treating conditions related to the PGI2 receptor |
KR20220119169A (ko) | 2017-03-01 | 2022-08-26 | 아레나 파마슈티칼스, 인크. | Pgi2-수용체 효능제를 포함하는 조성물 및 그의 제조 방법 |
-
2004
- 2004-02-11 DE DE102004006785A patent/DE102004006785A1/de not_active Withdrawn
-
2005
- 2005-02-09 WO PCT/EP2005/001277 patent/WO2005077863A1/de active Application Filing
- 2005-02-09 EP EP05701385A patent/EP1716087A1/de not_active Withdrawn
- 2005-02-09 CN CNA2005800109361A patent/CN1942419A/zh active Pending
- 2005-02-09 JP JP2006552532A patent/JP2007523077A/ja not_active Withdrawn
Non-Patent Citations (4)
Title |
---|
FRANZ EFFENBERGER UND KARL-HEINZ SCHÖNWALDER: "Die Acylierung von Ketonenolethern mit Malonyldichlorid - Eine neue Synthese von Phloroglucinen", CHEM. BER., vol. 117, 1984, pages 3270 - 3279, XP008047037 * |
HERBERT MAYR ET AL.: "Pi-Nucleophilicity in Carbon-Carbon Bond Forming Reactions", ACC. CHEM. RES., vol. 36, no. 1, 2003, pages 66 - 77, XP002328019 * |
JOHN P. RICHARD ET AL.: "Solvent Effects on Carbocation-Nucleophilic Combination Reactions: A Comparison of pi-Nucleophilicity in Aqueous and Organic Solvents", J. AM. CHEM. SOC., vol. 120, 1998, pages 10372 - 10378, XP002328017 * |
WEI ZHUANG AND KARL ANKER JORGENSON: "Friedel-Crafts reactions in water of carbonyl compounds with heteroaromatic compounds", CHEM. COMMUN., 2002, pages 1336 - 1337, XP002328018 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106866610A (zh) * | 2017-04-19 | 2017-06-20 | 齐齐哈尔大学 | 一种Lewis/Bronsted酸促进下醇参与的2‑氨基色烯衍生物N‑烷基化方法 |
CN106866610B (zh) * | 2017-04-19 | 2019-06-25 | 齐齐哈尔大学 | 一种Lewis/Bronsted酸促进下醇参与的2-氨基色烯衍生物N-烷基化方法 |
Also Published As
Publication number | Publication date |
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JP2007523077A (ja) | 2007-08-16 |
DE102004006785A1 (de) | 2005-09-08 |
CN1942419A (zh) | 2007-04-04 |
EP1716087A1 (de) | 2006-11-02 |
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