CN105693711A - Novel synthesis method for high-selectivity 2-amino and beta-amino five-membered heterocyclic compound - Google Patents
Novel synthesis method for high-selectivity 2-amino and beta-amino five-membered heterocyclic compound Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- C07D307/66—Nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
The invention belongs to the field of technical research of organic synthetic chemistry, and discloses a direct amination method for generating a 2-amino and beta-amino five-membered heterocyclic compound through a five-membered heterocyclic compound and various nitrogen sources by combining metal catalysis and organic catalysis.The limitation of direct amination of the five-membered heterocyclic compound is overcome, high selectivity of a 2-amino and beta-amino product is broken through, and various amination reagents can achieve the reaction.The amination reaction has the advantages that steps are simple, operation is easy, and raw materials, reagents and catalysts are easy to obtain, is applicable to synthesizing various 2-amino and beta-amino five-membered heterocyclic compounds, and is applicable to large-scale industrial production.
Description
Technical field:
The invention belongs to the technical field of research of Synthetic Organic Chemistry, relate to organic catalysis and the synthetic method of transition metal-catalyzed 2-amido and beta-amido five member ring heterocyclic compound。
Background technology:
Nitrogen-containing heterocycle compound is widely present in the middle of natural product and drug molecule, plays an important role in medicine and pesticide synthesis。Wherein, nitrogenous five member ring heterocyclic compound, due to the bio-pharmacology activity of its uniqueness, is synthesized in a large number by chemist and is studied (Davyt, D.；Serra, G.Mar.Drugs.8,2755, (2010)；Sheng, C.；Zhang, W.Eur.J.Med.Chem.45,3531, (2010))。Such as, the Olanzapine Tablets (Zyprexa) containing 2-amido thiophene molecular skeleton is constantly in before international drugs sales volume ranking list 100 in recent years；APE1 containing beta-amido thiophene molecular skeleton has good tubulin polymerization inhibitory action (Wang, X.；Sun, K.；Lv, Y.-H.；Ma, F.-J.；Li, G.；Li, D.-H.；Zhu, Z.-H.；Jiang, Y.-Q.Zhao, F.Chem.AsianJ.9,3413 (2014))。Therefore, the method particular importance of environmental protection, new and effective nitrogenous five-ring heterocycles class compound is developed。
Synthesizing nitrogenous five member ring heterocyclic compound before this to need to prepare complex precursor, reactions steps is loaded down with trivial details, and transformation efficiency is low, and by-product is more, and this method also faces the puzzlement that substrate spectrum is wide in range not simultaneously。(Stacy, G.W.；Villaescusa, F.W.；Wollner, T.E.J.Org.Chem.30,4074, (1965)；DelAmo, V.；Dubbaka, S.R.；Krasovskiy, A.；Knochel, P.Angew.Chem., Int.Ed.45,7838, (2006)；Androsov, D.A.；Solovyev, A.Y.；Petrov, M.L.；Butcher, R.J.；Jasinski, J.P.Tetrahedron, 66,2474, (2010)；Ablenas, F.；George, B.；Maleki, M.；Jain, R.；Hopkinson, A.；Lee-Ruff, E.Can.J.Chem.65,1800, (1987))。Along with in recent years intersect the developing rapidly of dehydrogenation coupling strategies (Li, C.-J.Acc.Chem.Res., 42,335, (2009)；LiZ.；Li, C.-J.J.Am.Chem.Soc., 127,3672, (2005)), it is possible to use simple raw material, experiences the atom utilization ratio of shorter synthetic route and Geng Gao, the organic molecule of synthesis series of complex。But five member ring heterocyclic compound, as: pyrroles, furan, thiophene is in intersection dehydrogenation aminating process, it is easy to oxidation reaction and the coupling reaction of self occur。Therefore, the catalyst system and catalyzing of novel and high-efficiency is developed, it is achieved the aminating reaction of five member ring heterocyclic compound is of crucial importance。
Documents:
1. publication number: CN1213048C title: a kind of heterocyclic compound-2-amido imidazo pyrroles's-6-ketone and method for making thereof and purposes
2. the patent No.: CN1890213 title: the method preparing the heterocyclic compound that N-amino replaces
3.KaiSun, etal.Copper-CatalyzedCross-DehydrogenativeC-NBondFormati onofAzineswithAzoles:OvercomingtheLimitationofOxidizingN-OActivationStrategy. < < ACSCatalysis > > 2015,5 (12), pp7194-7198.
Summary of the invention:
Instant invention overcomes current 2-amido five member ring heterocyclic compound synthesis step numerous and diverse, the limitation that combined coefficient is relatively low, utilize transition metal-catalyzed system, be prepared for series 2-amido five member ring heterocyclic compound by intersection dehydrogenation coupling。In conjunction with organic catalytic system, it is to avoid the route of synthesis that first halo replaces again, develop the synthetic method of the beta-amido ketone compounds of a kind of green, be prepared for a series of beta-amido five member ring heterocyclic compound。
Its reaction equation is as follows:
In formula, compound 1 can be furan, 2-methylfuran, 2-chlorine furan, 2-cyanofuran, 2-acetyl furan, 2-acetyl group-5-methylfuran, 3-fluoromethane man, thiophene, 2-acetyl thiophene, 2-methylthiophene, 2 acetyl thiophene, 2-methoxythiophene, 3-chlorothiophene, 3-methoxythiophene, pyrroles, N-methylpyrrole, N-benzenesulfonyl pyrroles, 2-acetyl pyrrole, N-methyl-2-acetyl pyrrole, 2-pyrrol-carboxylic acid's methyl ester, 3-bromine pyrroles etc.。Compound 2 can be saccharin and derivant, N-fluoro double; two benzsulfamide (NFSI), BTA, 1,2,4-triazole, pyrazoles, benzopyrazoles, imidazoles, purine, 6-chloropurines etc.。In condition A, slaine is the various salt compounds of copper, palladium, ruthenium, as: Schweinfurt green, copper trifluoromethanesulfcomposite, dichloride copper, Cu-lyt., palladium, palladium trifluoroacetate, ruthenium trichloride, ruthenous chloride；Oxidant is selectfluor；Solvent is Nitrocarbol. (CH3NO2), nitroethane (C2H5NO2), dichloroethanes (DCE)；In condition B, catalyst is tetrabutylammonium iodide (TBAI), tetrabutyl ammonium bromide (TBAB), tetrabutyl ammonium fluoride (TBAF), potassium iodide (KI)；Oxidant is tert-Butanol peroxide (TBHP), di-tert-butyl peroxide (DTBP), hydrogen peroxide (H2O2)；Solvent is ethyl acetate (EtOAc)。
Technical solution of the present invention is as follows:
Five yuan of heterocompounds are utilized to synthesize specifically comprising the following steps that of 2-amido five member ring heterocyclic compound with saccharin and derivant thereof
With pyrroles, furan, thiophene and derivatives for raw material；In reaction, nitrogenous source used is saccharin and derivant, N-fluoro double; two benzsulfamide (NFSI), BTA, 1,2,4-triazole, pyrazoles, benzopyrazoles, imidazoles, purine, 6-chloropurines etc.；Catalyst is Schweinfurt green, copper trifluoromethanesulfcomposite, dichloride copper, Cu-lyt., palladium, ruthenium trichloride, ruthenous chloride；Oxidant is selectfluor。To organic solvent Nitrocarbol. (CH3NO2), nitroethane (C2H5NO2) or dichloroethanes (DCE) 3.0～5.0 milliliters in add 1.0 mMs of above-mentioned heterocyclic compounds and 1.1 mMs of nitrogenous sources。Add above-mentioned 0.1 mM of metallic catalyst, 1.5 mMs of oxidants finish, oil bath 90～120 degrees Celsius, stir 3～12 hours, post-treated separation obtains 2-amido heterocyclic compound, productivity depending on differential responses between 71%～97% (above quantity can scale up)。Refer to the embodiment in detailed description of the invention。
Five yuan of heterocompounds are utilized to synthesize specifically comprising the following steps that of beta-amido five member ring heterocyclic compound with saccharin and derivant thereof
With the pyrroles of acetyl group replacement, furan, thiophene and derivatives for raw material；In reaction, nitrogenous source used is nitrogenous source is saccharin and derivant, N-fluoro double; two benzsulfamide (NFSI), BTA, 1,2,4-triazole, pyrazoles, benzopyrazoles, imidazoles, purine, 6-chloropurines etc.；Catalyst is tetrabutylammonium iodide, tetrabutyl ammonium bromide, tetrabutyl ammonium fluoride, potassium iodide；Oxidant is tert-Butanol peroxide, di-tert-butyl peroxide, hydrogen peroxide。1.0 mMs of above-mentioned heterocyclic compounds and 1.1 mMs of nitrogenous sources are added in organic solvent ethyl acetate 3.0～5.0 milliliters。Add above-mentioned 0.2 mM of organic catalyst, 2.0 mMs of oxidants finish, oil bath 90～120 degrees Celsius, stir 3～12 hours, post-treated separation obtains beta-amido heterocyclic compound, productivity depending on differential responses between 76%～92% (above quantity can scale up)。Refer to the embodiment in detailed description of the invention。
Accompanying drawing explanation
Fig. 1 to Fig. 5 is representative 2-amido heterocyclic compound1H-NMR spectrum。
Fig. 6 and Fig. 7 is representative beta-amido heterocyclic compound1H-NMR spectrum。
Detailed description of the invention
Embodiment 1:
In 50 milliliters of round-bottomed flasks; add 0.1103 gram of (1.0 mMs) 2-acetyl furan; 0.2015 gram of (1.1 mMs) saccharin; 0.0182 gram of (0.1 mM) Schweinfurt green; 0.7080 gram of (2.0 mMs) selectfluor; 6.0 milliliters of dimethyl sulfoxides (DMSO), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to 2-acetyl furan。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2648 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 91%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid.Mp:247-249 DEG C；1HNMR (400MHz；CDCl3): δ=2.54 (s, 3H), 6.81 (d, J=3.6Hz, 1H), 7.32 (d, J=3.6Hz, 1H), 7.95-8.03 (m, 3H), 8.20 (d, J=7.2Hz, 1H).
Embodiment 2:
In 50 milliliters of round-bottomed flasks; add 0.1260 gram of (1.0 mMs) 2-acetyl thiophene; 0.2015 gram of (1.1 mMs) saccharin; 0.0182 gram of (0.1 mM) Schweinfurt green; 0.7080 gram of (2.0 mMs) selectfluor; 6.0 milliliters of dimethyl sulfoxides (DMSO), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to 2-acetyl thiophene。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2671 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 87%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid.Mp:238-239 DEG C；1HNMR (400MHz；CDCl3): δ=2.59 (s, 3H), 7.38 (d, J=4.0Hz, 1H), 7.69 (d, J=4.4Hz, 1H), 7.95-8.05 (m, 3H), 8.21 (d, J=6.8Hz, 1H).
Embodiment 3
In 50 milliliters of round-bottomed flasks; add 0.1103 gram of (1.0 mMs) 2-acetyl furan; 0.1309 gram of (1.1 mMs) BTA; 0.0182 gram of (0.1 mM) Schweinfurt green; 0.7080 gram of (2.0 mMs) selectfluor; 6.0 milliliters of dimethyl sulfoxides (DMSO), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to 2-acetyl furan。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2648 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 91%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid.Mp:234-235 DEG C；1HNMR (400MHz；CDCl3): δ=2.43 (s, 3H), 7.17-7.47 (m, 3H), 7.60 (t, J=7.6,1H), 7.77 (d, J=8.4,1H), 8.15 (d, J=8.4,1H).
Embodiment 4
In 50 milliliters of round-bottomed flasks; add 0.1103 gram of (1.0 mMs) 2-acetyl furan; 0.3153 gram of (2.0 mMs) N-fluoro-diphenyl sulfimide; 0.0182 gram of (0.1 mM) Schweinfurt green; 0.7080 gram of (2.0 mMs) selectfluor; 6.0 milliliters of dimethyl sulfoxides (DMSO), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to 2-acetyl furan。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2648 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 91%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid.Mp:214-216 DEG C；1HNMR (400MHz；CDCl3): δ=2.39 (s, 3H), 6.38 (d, J=3.6Hz, 1H), 7.17 (d, J=3.6Hz, 1H), 7.61 (t, J=7.6Hz, 4H), 7.73 (d, J=7.2Hz, 2H), 8.01 (t, J=7.2Hz, 4H).
Embodiment 5:
In 50 milliliters of round-bottomed flasks, add 0.0670 gram of (1.0 mMs) pyrroles, 0.2015 gram of (1.1 mMs) saccharin, 0.0182 gram of (0.1 mM) Schweinfurt green, 0.7080 gram of (2.0 mMs) selectfluor, 6.0 milliliters of dimethyl sulfoxides (DMSO), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to pyrroles。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2331 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 94%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid；Mp:212-214 DEG C；1HNMR (500MHz；CDCl3): δ=6.35 (dd, J1=3.0Hz, J2=6.0Hz, 1H), 6.48-6.50 (m, 1H), 6.90-6.91 (m, 1H), 7.87-7.95 (m, 2H), 8.00 (d, J=7.5Hz, 1H), 8.14 (d, J=7.5,1H), 8.68 (s, 1H).
Embodiment 6:
In 50 milliliters of round-bottomed flasks; add 0.1103 gram of (1.0 mMs) 2-acetyl furan; 0.2015 gram of (1.1 mMs) saccharin; 0.0739 gram of (0.2 mM) tetrabutylammonium iodide; 0.1802 gram of (2.0 mMs) tert-Butanol peroxide; 6.0 milliliters of ethyl acetate (EtOAc), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to 2-acetyl furan。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2794 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 96%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid.Mp:252-254 DEG C；1HNMR (400MHz；CDCl3): δ=5.04 (s, 2H), 6.63 (t, J=2.8Hz, 1H), 7.36 (d, J=2.8Hz, 1H), 7.87-7.98 (m, 4H), 8.12 (d, J=7.2Hz, 1H).
Embodiment 7:
In 50 milliliters of round-bottomed flasks; add 0.1260 gram of (1.0 mMs) 2-acetyl thiophene; 0.2015 gram of (1.1 mMs) saccharin; 0.0739 gram of (0.2 mM) tetrabutylammonium iodide; 0.1802 gram of (2.0 mMs) tert-Butanol peroxide; 6.0 milliliters of ethyl acetate (EtOAc), heat 120 DEG C, react 3 hours and react completely (thin layer chromatography TLC monitoring) to 2-acetyl furan。Reactant mixture is poured in 20 milliliters of water, with extraction into ethyl acetate (10 milliliters × 3)。Merge organic facies, dry with anhydrous sodium sulfate。After solvent is evaporated off, it is 0.2794 gram that residue obtains white solid through silica gel column chromatography separation (eluent: petrol ether/ethyl acetate=6/1), productivity 96%。Following formula is shown in reaction:
Spectrum elucidation data
Whitesolid.Mp:227-229 DEG C；1HNMR (400MHz；CDCl3): δ=5.08 (s, 2H), 7.23 (dd, J1=4.0Hz, J2=4.8Hz, 1H), 7.77 (dd, J1=0.8Hz, J2=4.8Hz, 1H), 7.87-8.11 (m, 4H), 8.12 (d, J=6.8Hz, 1H)。
Claims (6)
1. utilizing metallic catalyst or organic catalyst to achieve the efficient selective aminating reaction of five member ring heterocyclic compound and amination reagent, be prepared for series 2-amido and beta-amido five member ring heterocyclic compound, its characteristic reaction formula is as follows:
。
2. in formula, compound 1 can be furan, 2-methylfuran, 2-chlorine furan, 2-cyanofuran, 2-acetyl furan, 2-acetyl group-5-methylfuran, 3-methylfuran, thiophene, 2-acetyl thiophene, 2-methylthiophene, 2 acetyl thiophene, 2-methoxythiophene, 3-chlorothiophene, 3-methoxythiophene, pyrroles, N-methylpyrrole, N-benzenesulfonyl pyrroles, 2-acetyl pyrrole, N-methyl-2-acetyl pyrrole, 2-pyrrol-carboxylic acid's methyl ester, 3-bromine pyrroles etc.。Compound 2 can be saccharin and derivant, N-fluoro double; two benzsulfamide (NFSI), BTA, 1,2,4-triazole, pyrazoles, benzopyrazoles, imidazoles, purine, 6-chloropurines etc.。
3. the metal salt catalyst in claim 1 is Schweinfurt green, copper trifluoromethanesulfcomposite, dichloride copper, Cu-lyt., palladium, palladium trifluoroacetate, ruthenium trichloride, ruthenous chloride；Organic catalyst is tetrabutylammonium iodide, tetrabutyl ammonium bromide, tetrabutyl ammonium fluoride, potassium iodide；Catalyst is 0.02～0.2: 1 with the amount ratio of heterocyclic compound in claim 1。
4. in claim 1, oxidant is selectfluor, tert-Butanol peroxide, di-tert-butyl peroxide, hydrogen peroxide, and oxidant is 1.1～2: 1 with the amount ratio of heterocyclic compound in claim 1。
5. in claim 1, solvent is Nitrocarbol., nitroethane, dichloroethanes, ethyl acetate。
6. in claim 1, temperature controls at 90～120 DEG C。
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| CN107619379A (en) * | 2017-10-17 | 2018-01-23 | 安阳师范学院 | A kind of preparation method of 2 amido azo aromatic compound |
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| CN103623714A (en) * | 2013-12-02 | 2014-03-12 | 厦门理工学院 | Method for preparing nonpolar polyvinylidene fluoride ultrafiltration membrane |
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| KAI SUN ET AL.: "Copper-Catalyzed Cross-Dehydrogenative C-N Bond Formation of Azines with Azoles:Overcoming the Limitation of Oxidizing N-O Activation Strategy", 《ACS CATAL.》 * |
| SICHANG WANG ET AL.: "Copper-Catalyzed Direct Amidation of Heterocycles with N-Fluorobenzenesulfonimide", 《ORG. LETT.》 * |
| XIN WANG ET AL.: "Regioselective C-H Imidation of Five-Membered Heterocyclic Compounds through a Metal Catalytic or Organocatalytic Approach", 《CHEM. ASIAN J.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107619379A (en) * | 2017-10-17 | 2018-01-23 | 安阳师范学院 | A kind of preparation method of 2 amido azo aromatic compound |
| CN107619379B (en) * | 2017-10-17 | 2018-07-24 | 安阳师范学院 | A kind of preparation method of 2- amidos azo aromatic compound |
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